NZ748767B2 - Picolinamide compounds with fungicidal activity - Google Patents
Picolinamide compounds with fungicidal activity Download PDFInfo
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- NZ748767B2 NZ748767B2 NZ748767A NZ74876715A NZ748767B2 NZ 748767 B2 NZ748767 B2 NZ 748767B2 NZ 748767 A NZ748767 A NZ 748767A NZ 74876715 A NZ74876715 A NZ 74876715A NZ 748767 B2 NZ748767 B2 NZ 748767B2
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- 230000000855 fungicidal effect Effects 0.000 title abstract description 37
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 151
- 239000000417 fungicide Substances 0.000 claims abstract description 36
- -1 arthropodicides Substances 0.000 claims description 126
- 239000000203 mixture Substances 0.000 claims description 102
- 239000000575 pesticide Substances 0.000 claims description 7
- 239000002917 insecticide Substances 0.000 claims description 4
- 239000000642 acaricide Substances 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 239000003899 bactericide agent Substances 0.000 claims description 3
- 239000012876 carrier material Substances 0.000 claims description 3
- 230000001069 nematicidal effect Effects 0.000 claims description 2
- 239000005645 nematicide Substances 0.000 claims description 2
- 241000233866 Fungi Species 0.000 abstract description 6
- 238000011160 research Methods 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 547
- 101150041968 CDC13 gene Proteins 0.000 description 543
- 238000005481 NMR spectroscopy Methods 0.000 description 439
- 238000005160 1H NMR spectroscopy Methods 0.000 description 405
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 249
- 239000012230 colorless oil Substances 0.000 description 192
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 158
- 239000006260 foam Substances 0.000 description 156
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 86
- 239000003921 oil Substances 0.000 description 86
- 235000019198 oils Nutrition 0.000 description 86
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 77
- 239000007787 solid Substances 0.000 description 70
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- IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 60
- 241000196324 Embryophyta Species 0.000 description 59
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- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 35
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- 238000000034 method Methods 0.000 description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 201000010099 disease Diseases 0.000 description 28
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- 238000002360 preparation method Methods 0.000 description 28
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
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- 235000011152 sodium sulphate Nutrition 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- 239000007832 Na2SO4 Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- 206010003402 Arthropod sting Diseases 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
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- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
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- 230000002950 deficient Effects 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000011081 inoculation Methods 0.000 description 7
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- 125000001424 substituent group Chemical group 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
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- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
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- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
-
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- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/20—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
-
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
-
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
This disclosure relates to picolinamides of Formula I and their use as fungicides. Fungicides are compounds, of natural or synthetic origin, which act to protect and/or cure plants against damage caused by agriculturally relevant fungi. Generally, no single fungicide is useful in all situations. Consequently, research is ongoing to produce fungicides that may have better performance, are easier to use, and cost less.
Description
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by an
PICOLINAMIDE COMPOUNDS WITH FUNGICIDAL TY
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a divisional of New Zealand patent application no. 732641, which
claims the benefit of U.S. Provisional Patent Application Serial Nos. 62/098120 filed December 30,
2014 and 62/098122 filed December 30, 2014, which are expressly incorporated by reference
herein.
BACKGROUND & SUMMARY
[0002] ides are compounds, of natural or synthetic origin, which act to protect and/or
cure plants against damage caused by agriculturally relevant fungi. Generally, no single fungicide is
useful in all ions. Consequently, research is ongoing to produce fungicides that may have
better performance, are easier to use, and cost less.
The present disclosure relates to picolinamides and their use as fungicides. The
compounds of the t disclosure may offer protection t ascomycetes, basidiomycetes,
deuteromycetes and oomycetes.
One embodiment of the present disclosure may include compounds of Formula I:
in which: X is hydrogen or C(O)R5;
Y is hydrogen, C(O)R5, or Q;
wherein: Z is N or CH;
R1 is hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R8;
R2 is methyl;
R1 is chosen from aryl or heteroaryl, each ally substituted with 0, I or multiple
R? is chosen from hydrogen, halo, hydroxyl, alkyl or alkoxy;
R5 is chosen from alkoxy or oxy, each optionally substituted with 0, 1, or
multiple Rx;
&, is chosen from hydrogen, alkoxy, or halo, each optionally tuted with 0, 1, or
multiple Rx;
R7 is chosen from hydrogen,-C(O)R9, or-CH2OC(O)R9;
R8 is chosen from hydrogen, alkyl, aryl, acyl, halo, alkenyl, l, alkoxy, cyano or
l 0 heterocyclyl, each optionally substituted with 0, 1, or multiple R10;
R9 is chosen from alkyl, alkoxy, or aryl, each optionally substituted with 0, 1, or
multiple Rx;
R10 is chosen from hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkoxy, or heterocyclyl;
R11 is chosen fromhydrogen or alkyl, substituted with 0, I, or multiple R8;
R12 is chosen from aryl or heteroaryl, each ally substituted with 0, 1 or multiple
Another embodiment ofthe present disclosure may include a fungicidal composition
for the control or prevention offungal attack comprising the compounds described above and a
ogically acceptable carrier material.
[00061 Yet another embodiment ofthe present disclosure may inclucle a method for the
control or prevention of fungal attack on a plant, the method including the steps of applying a
fungicidally effective amount ofone or more ofthe compounds bed above to at least one of
the fungus, the plant, and an area adjacent to the plant.
[00071 It will be understood by those skilled in the art that the following terms may include
generic "R"-groups within their definitions, e.g., "the term alkoxy refers to an-OR substituent". It is
also tood that within the definitions for the following terms, these "R" groups are included for
illustration purposes and should not be construed as limiting or being limited by substitutions about
Formula I.
The term "alkyl" refers to a branched, unbranched, or saturated cyclic carbon chain,
ing, but not limited to, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tertiary butyl, pentyl,
hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
100091 The term yl" refers to a branched,unbranched or cyclic carbon chain containing
one or more double bonds including, but not limited to, ethenyl,propenyl,butenyl, isopropenyl,
enyl,cyclobutenyl,cyclopentenyl,cyclohexenyl,and the like.
The term "alkynyl" refers to a branched or unbranched carbon chain containing one or
more triple bonds including,but not limited to,propynyl,butynyl,and the like.
The terms "aryl" and "Ar" refer to any ic ring, mono- or bi-cyclic,containing 0
heteroatoms.
[0012J The term "heterocyclyl" refers to any aromatic or non-aromatic ring, mono- or bicyclic
,containing one or more heteroatoms.
[0013J The term y" refers to an-OR substituent.
[00141 The term "acyloxy" refers to an-OC(O)R substituent.
[0015J The term "cyano" refers to a-C=N substituent.
The term "hydroxyl" refers to an-OH tuent.
100171 The term "amino" refers to a-N(Rh substituent.
[0018] The term "arylalkoxy" refers to-O(CH2)11Ar where n is an integer selected from the
list l,2,3,4,5,or6.
The term "haloalkoxy" refers to an-OR-Xsubstituent, wherein Xis Cl,F, Br, or I,or
any combination thereof
The term "haloalkyl" refers to an alkyl,which is substituted with Cl, F,I,or Br or any
ation thereof
[0021J The term "halogen" or "halo" refers to one or more halogen atoms, defined as F, Cl,
Br, and I.
[0022J The term "nitro" refers to a-N02 substituent.
[00231 The term thioalkyl refers to an-SR substituent.
[0024J Throughout the sure, reference to the compounds ofFormula I is read as also
including all isomers, for example diastereomers, enantiomers, and mixtures thereof. In
r embodiment, Formula I is read as also including salts or hydrates thereof. Exemplary salts
include, but are not limited to: hydrochloride, hydrobromide, hydroiodide, trifluoroacetate, and
trifluoromethane sulfonate.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
100251 It is also understood by those skilled in the art that additional substitution is allowable,
unless otherwise noted, as long as the rules of chemical bonding and strain energy are satisfied and
the product still exhibits fungicidal activity
Another embodiment ofthe present disclosure is a use ofa nd ofFormula I,
for protection of a plant against attack by a phytopathogenic organism or the treatment of a plant
infested by a phytopathogenic organism, comprising the application of a compound ofFormula I, or
a composition comprising the compound to soil, a plant, a part ofa plant, foliage, and/or roots.
[0027J Additionally, another embodiment ofthe present disclosure is a composition useful for
protecting a plant against attack by a phytopathogenic organism and/or treatment of a plant infested
by a phytopathogenic organism comprising a compound ofFormula I and a phytologically
acceptable carrier material.
DETAILED DESCRIPTION
100281 The compounds ofthe present sure may be applied by any of a variety of known
techniques, either as the compounds or as formulations comprising the compounds. For example,
the compounds may be applied to the roots or e of plants for the control of various fungi,
without damaging the commercial value ofthe plants. The als may be applied in the form of
any of the generally used formulation types, for example, as solutions, dusts, wettable powders,
flowable concentrate, or emulsifiable concentrates.
[00291 Preferably, the compounds ofthe present disclosure are applied in the form of a
formulation, comprising one or more ofthe nds ofFormula I with a phytologically
able carrier. Concentrated formulations may be sed in water, or other s, for
application, or formulations may be dust-like or granular, which may then be applied without
further treatment The formulations can be prepared according to procedures that are conventional
in the agricultural chemical a11.
The present disclosure contemplates all es by which one or more of the
compounds may be formulated for ry and use as a fungicide. Typically, formulations are
applied as aqueous suspensions or emulsions. Such suspensions or emulsions may be ed
from water-soluble, water-suspendible, or emulsifiable ations which are solids, usually
known as le powders; or liquids, usually known as emulsifiable concentrates, aqueous
suspensions, or suspension concentrates. As will be readily appreciated, any material to which these
[Annotation] Mel.Chan
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[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
compounds may be added may be used, provided it yields the desired utility without significant
interference with the ty of these compounds as ngal agents.
100311 le powders, which may be ted to form water-dispersible es,
comprise an intimate mixture ofone or more of the compounds ofFormula I, an inert r and
surfactants The concentration ofthe compound in the wettable powder may be from about l 0
percent to about 90 percent by weight based on the total weight of the wettable powder, more
preferably about 25 ,veight t to about 75 weight t In the preparation of wettable
powder formulations, the compounds may be compounded with any finely divided solid, such as
prophyllite, talc, chalk, gypsum, 's earth, bentonite, attapulgite, starch, casein, gluten,
l O montmorillonite clays, diatomaceous earths, purified silicates or the like. In such ions, the
finely d carrier and surfactants are typically blended with the compound(s) and milled.
[0032J fiable concentrates of the compounds of Formula I may comprise a convenient
concentration, such as from about I weight percent to about 50 weight percent of the compound, in
a suitable liquid, based on the total weight ofthe concentrate. The compounds may be dissolved in
an inert carrier, which is either a water-miscible solvent or a mixture of water-immiscible organic
solvents, and emulsifiers. The concentrates may be diluted with water and oil to form spray
mixtures in the form of oil-in-water emulsions. Useful organic solvents include aromatics,
especially the oiling naphthalenic and olefinic portions of petroleum such as heavy aromatic
naphtha. Other organic solvents may also be used, for example, terpenic solvents, including rosin
derivatives, aliphatic ketones, such as cyclohexanone, and complex alcohols, such as 2-
ethanol.
[00331 Emulsifiers which may be advantageously employed herein may be readily
determined by those skilled in the art and include various nonionic, anionic, cationic and amphoteric
emulsifiers, or a blend oftwo or more emulsifiers. Examples of nonionic emulsifiers useful in
ing the emulsifiable concentrates include the polyalkylene glycol ethers and condensation
products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene
oxide, propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with
the polyol or polyoxyalkylene. Cationic emulsifiers include nary ammonium compounds and
fatty amine salts. Anionic emulsifiers include the oil-soluble salts (e.g., calcium) of alkylaryl
sulfonic acids, oil-soluble salts or sulfated polyglycol ethers and appropriate salts ofphosphated
polyglycol ether.
[Annotation] Mel.Chan
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[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
100341 Representative organic s which may be employed in preparing the emulsifiable
concentrates of the compounds of the present disclosure are the aromatic liquids such as xylene,
propyl benzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic
liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, particularly the
dimethyl amides of fatty glycols and glycol derivatives such as then-butyl ether, ethyl ether or
methyl ether of diethylene glycol, the methyl ether of ylene glycol, petroleum fractions or
hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such
as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, t oil, corn oil, cottonseed
oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the
l O above vegetable oils; and the like. es of two or more organic liquids may also be employed in
the preparation of the emulsifiable concentrate. Organic liquids include xylene, and propyl e
fractions, with xylene being most preferred in some cases. Sutiace-active dispersing agents are
typically employed in liquid formulations and in an amount of from 0.1 to 20 percent by weight
based on the combined weight of the dispersing agent with one or more of the compounds. The
formulations can also contain other compatible additives, for example, plant growth tors and
other biologically active compounds used in agriculture.
Aqueous suspensions comprise sions of one or more water-insoluble
compounds of Formula I, dispersed in an aqueous vehicle at a concentration in the range from about
1 to about 50 weight percent, based on the total weight of the aqueous suspension. Suspensions are
prepared by finely grinding one or more of the nds, and vigorously mixing the ground
material into a vehicle comprised of water and tants chosen from the same types discussed
above. Other components, such as inorganic salts and tic or natural gums, may also be added
to increase the density and ity of the aqueous vehicle.
[00361 The compounds of a I can also be applied as granular formulations, which are
particularly useful for applications to the soil. ar formulations generally contain from about
0.5 to about 10 weight percent, based on the total weight of the granular formulation of the
compound(s), dispersed in an inert carrier which consists entirely or in large part of coarsely divided
inert material such as attapulgite, bentonite, diatomite, clay or a similar inexpensive substance. Such
formulations are usually prepared by dissolving the compounds in a suitable solvent and ng it
to a granular carrier which has been preformed to the appropriate particle size, in the range of from
about 0.5 to about 3 mm. A suitable solvent is a solvent in which the compound is substantially or
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
completely soluble. Such formulations may also be prepared by making a dough or paste of the
carrier and the compound and solvent, and crushing and drying to obtain the desired granular
particle.
Dusts containing the compounds of a I may be prepared by intimately mixing
one or more of the compounds in powdered form with a suitable dusty agricultural carrier, such as,
for example, kaolin clay, ground ic rock, and the like. Dusts can suitably contain from about
1 to about 10 weight t of the compounds, based on the total weight of the dust
[0038J The formulations may additionally contain adjuvant surfactants to enhance deposition,
wetting, and penetration of the compounds onto the target crop and sm. These adjuvant
tants may optionally be employed as a component of the formulation or as a tank mix. The
amount of adjuvant surfactant will typically vary from 0.01 to 1.0 percent by volume, based on a
spray-volume of water, preferably 0.05 to 0.5 volume percent le adjuvant swfactants include,
but are not limited to ethoxylated nonyl phenols, ethoxylated synthetic or l alcohols, salts of
the esters or sulfosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines, blends of
surfactants with mineral or ble oils, crop oil concentrate (mineral oil (85%) + emulsifiers
( 15%)); henol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of
petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9- Cu
alkylpolyglycoside; phosphated alcohol ethoxylate; l primary alcohol (C 12 - C 1r,) ethoxylate;
di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate +
urea ammonium nitrrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate
(8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99. The formulations may also include
oil-in-water emulsions such as those sed in US Patent Application Serial No. 11/495,228, the
disclosure of which is sly incorporated by nce herein.
[00391 The formulations may optionally include ations that contain other pesticidal
compounds. Such additional idal compounds may be fungicides, insecticides, herbicides,
cides, miticides, arthropodicides, bactericides or combinations thereof that are compatible
with the compounds of the present disclosure in the medium selected for application, and not
antagonistic to the activity of the present compounds. Accordingly, in such embodiments, the other
pesticidal compound is employed as a supplemental toxicant for the same or for a different
pesticidal use. The compounds of Formula I and the pesticidal compound in the combination can
generally be present in a weight ratio of from 1:100 to100:1.
[Annotation] Mel.Chan
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ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
100401 The compounds of the present disclosure may also be ed with other fungicides
to form fungicidal mixtures and synergistic mixtures thereof. The fungicidal compounds of the
present disclosure are often applied in conjunction with one or more other fungicides to control a
wider variety of undesirable diseases. When used in conjunction with other ide(s), the
presently claimed compounds may be formulated with the other fungicide(s), ixed with the
other fungicide(s) or applied sequentially with the other fungicide(s). Such other fungicides may
include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline e,
ametoctradin, amisulbrom, antimycin, myces quisqualis, azaconazole, azoxystrobin, Bacillus
subti!is, Bacillus subti!is strain QST713, benalaxyl, benomyl, benthiavalicarb-isopropyl,
indiflupyr, benzylaminobenzene-sulfonate (BABS) salt, bicarbonates, biphenyl,
bismerthiazol, anol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole,
bupirimate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, carvone,
chlazafenone, chloroneb, chlorothalonil, chlozolinate, Coniothyrium ns, copper hydroxide,
copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), coumoxystrobin,
cuprous oxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet,
debacarb, diammonium ethylenebis-(dithiocarbamate), dichlotluanid, dichlorophen, diclocymet,
diclomezine, dichloran, fencarb, difenoconazole, difenzoquat ion, diflumetorim,
dimethomorph, dimoxystrobin, nazole, diniconazole-M, dinobuton, dinocap, diphenylamine,
dipymetitrone, dithianon, dodemorph, dodemorph acetate, dodine, dodine free base, edifenphos,
enestrobin, enestroburin, enoxastrobin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole,
famoxadone, fenamidone, fenaminostrobin, fenarimol, fenbuconazole, fenfuram, fenhexamid,
fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, azamine, fentin, fentin acetate, fentin
hydroxide, , one, fluazinam, fludioxonil, flufenoxystrobin, flumorph, fluopicolide,
tluopyram, imide, tluoxastrobin, tluquinconazole, tlusilazole, tlusulfamide, tlutianil,
anil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminium, fuberidazole,
furalaxyl, furametpyr, guazatine, guazatine acetates, GY-81, hexachlorobenzene, hexaconazole,
hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine, tadine triacetate,
iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione,
iprovalicarb, isofetamid, isoprothiolane, isopyrazam, nil, kasugamycin, kasugamycin
hydrochloride hydrate, kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin,
mandipropamid, maneb, mefenoxam, mepanipyrim, mepronil, -dinocap, mercuric chloride,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
mercuric oxide, mercurous chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metampotassium
, metam-sodium, metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate,
metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl,
nuarimol, octhilinone, ofurace, oleic acid (fatty acids), orysastrobin, yl, oxathiapiprolin,
oxine-copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron,
penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercury acetate,
phosphonic acid, phthalide, picarbutrazox, picoxystrobin, polyoxin B, polyoxins, polyoxorim,
potassium bicarbonate, potassium hydroxyquinoline sulfate, azole, prochloraz, procymidone,
propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothioconazole,
l 0 pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyraziflumid, pyrazophos, pyribencarb,
pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyrisoxazole, pyroquilon, quinoclamine,
quinoxyfen, quintozene, Rey11011tria sachalinensis extract, sedaxane, silthiofam, simeconazole,
sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, amine,
sulfur, SYP-Z048, tar oils, tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole,
thifluzamide, anate-methyl, thiram, tiadinil, tolclofos-methyl, carb, luanid,
triadimefon, triadimenol, triazoxide, triclopyricarb, tricyclazole, tridemorph, xystrobin,
triflumizole, triforine, triticonazole, validamycin, nalate, valiphenal, vinclozolin, zineb, ziram,
zoxamide, Candida ila,F11sari11m l)()rllm, Gliodadi11m spp., Phlehiopsis gigan/ea,
Streptomyces griseoviridis, Trichoderma spp., (RS)-N-(3,5-dichl oropheny1)(methoxymethy1)-
succinimide, 1,2-dichloropropane, 1,3-dichloro-1, 1,3,3-tetrafluoroacetone hydrate, 1-chloro-2,4-
dinitronaphthalene, l-chloronitropropane, 2-(2-heptadecylimidazolin-l-yl)ethanol, 2,3-
dihydrophenyl-1,4-dithi-ine 1,1,4,4-tetraoxide, 2-methoxyethylmercury acetate, 2-
methoxyethylmercury chloride, 2-methoxyethylmercury silicate, hlorophenyl)
methylrhodanine, 4-(2-nitropropenyl)phenyl thiocyanateme, ampropylfos, ine, azithiram,
barium polysulfide, Bayer 32394, benodanil, benquinox, bentaluron, acril, acrilisobutyl
, benzamorf, binapacryl, thylmercury) sulfate, bis(tributyltin) oxide, buthiobate,
m calcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone,
chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis(3-phenylsalicylate), copper
zinc chromate, eb, cupric hydrazinium sulfate, cuprobam, cyclafuramid, cypendazole,
cyprofuram, decafentin, dichlone, dichlozoline, diclobutrazol, dimethirimol, dinocton, dinosulfon,
dinoterbon, dipyrithione, ditalimfos, dodicin, drazoxolon, EBP, ESBP, etaconazole, etem, ethirim,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
nosult? fenapanil, fenitropan, imazole, furcarbanil, furconazole, furconazole-cis,
furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos,
ICIA0858, isopamphos, isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam,
methylmercury dicyandiamide, fovax, , mucochloric anhydride, myclozolin, N-3,SS
dichlorophenyl-succinimide, trophenylitaconimide, natamycin, N-ethylmercurio
toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercury
dimethyldithiocarbamate, phenylmercury e, phosdiphen, prothiocarb, prothiocarb
hydrochloride, pyracarbolid, nitril, pyroxychlor, pyroxyfur, quinacetol, quinacetol sulfate,
quinazamid, quinconazole, rabenzazole, salicylanilide, 9, sultropen, tecoram, thiadifluor,
l O thicyofen, thiochlo1fonphim, thiophanate, thioquinox, id, triamiphos, triarimol, triazbutil,
trichlamide, urbacid, zarilamid, and any combinations thereof.
[0041J Additionally, the compounds bed herein may be combined with other pesticides,
including insecticides, nematocides, miticides, arthropodicides, bactericides or combinations thereof
that are compatible \vith the compounds of the present disclosure in the medium selected for
application, and not antagonistic to the activity of the present compounds to form idal
es and istic mixtures thereof The fungicidal compounds ofthe present disclosure may
be applied in ction with one or more other pesticides to control a wider variety of undesirable
pests. When used in conjunction with other pesticides, the presently claimed compounds may be
formulated with the other pesticide(s), tank-mixed with the other pesticide(s) or applied sequentially
with the other pesticide(s). Typical insecticides include, but are not limited to: 1,2-dichloropropane,
abamectin, acephate, acetamiprid, acethion, acetoprole, acrinathrin, acrylonitrile, afidopyropen,
alanycarb, aldicarb, carb, aldrin, allethrin, allosamidin, allyxycarb, alpha-cypermethrin,
alpha-ecdysone, alpha-endosulfan, amidithion, aminocarb, amiton, amiton oxalate, amitraz,
anabasine, thion, azadirachtin, azamethiphos, azinphos-ethyl, azinphos-methyl, azothoate,
barium hexafluorosilicate, in, bendiocarb, benfuracarb, bensultap, beta-cyfluthrin, betacypermethrin
, bifenthrin, bioallethrin, anomethrin, biopermethrin, bistrifluron, borax, boric
acid, broflanilide, nvinfos, bromocyclen, bromo-DDT, bromophos, bromophos-ethyl,
bufencarb, buprofezin, butacarb, butathiofos, butocarboxim, butonate, butoxycarboxim, cadusafos,
calcium arsenate, calcium lfide, camphechlor, carbanolate, yl, carbofuran, carbon
disulfide, carbon tetrachloride, carbophenothion, carbosulfan, cartap, cartap hydrochloride,
chlorantraniliprole, chlorbicyclen, chlordane, chlordecone, chlordimeform, chlordimeform
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
hydrochloride, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlortluazuron, chlormephos,
chloroform, picrin, chlorphoxim, chlorprazophos, chlorpyrifos, chlorpyrifos-methyl,
chlorthiophos, chromafenozide, cinerin I, n II, cinerins, cismethrin, clacyfos, cloethocarb,
closantel, clothianidin, copper acetoarsenite, copper arsenate, copper naphthenate, copper ,
coumaphos, coumithoate, crotamiton, crotoxyphos, cmfomate, cryolite, cyanofenphos, cyanophos,
cyanthoate, cyantraniliprole, cyclaniliprole, cyclethrin, cycloprothrin, cytluthrin, cyhalothrin,
cypermethrin, cyphenothrin, cyromazine, cythioate, DDT, decarbofuran, deltamethrin, demephion,
demephion-O, demephion-S, n, demeton-methyl, demeton-O, demeton-O-methyl, demeton
S, demeton-S-methyl, demeton-S-methylsulphon, thiuron, dialifos, diatomaceous earth,
l O on, dicapthon, dichlofenthion, dichlorvos, dicloromezotiaz, dicresyl, dicrotophos, dicyclanil,
dieldrin, ditlubenzuron, dilor, dimefluthrin, dimefox, dimetan, dimethoate, dimethrin,
dimethylvinphos, dimetilan, dinex, dinex-diclexine, dinoprop, dinosam, dinotefuran, diofenolan,
dioxabenzofos, dioxacarb, dioxathion, disulfoton, dithicrofos, d-limonene, DNOC, DNOC
ammonium, DNOC-potassium, DNOC-sodium, ctin, ecdysterone, tin, emamectin
te, EMPC, hrin, endosulfan, endothion, endrin, EPN, epofenonane, eprinomectin,
esdepallethrine, alerate, etaphos, ethiofencarb, ethion, ethiprole, ethoate-methyl, ethoprophos,
ethyl formate, ethyl-DDD, ne dibromide, ethylene dichloride, ethylene oxide, etofenprox,
os, EXD, famphur, fenamiphos, fenazatlor, fenchlorphos, fenethacarb, fentluthrin,
fenitrothion, fenobucarb, fenoxacrim, fenoxycarb, fenpirithrin, fenpropathrin, fensulfothion,
fenthion, fenthion-ethyl, fenvalerate, fipronil, tlometoquin, tlonicamid, tlubendiamide, tlucofuron,
flucycloxuron, flucythrinate, flufenerim, flufenoxuron, prox, flufiprole, fluhexafon,
tlupyradifurone, tluvalinate, fonofos, formetanate, formetanate hloride, formothion,
formparanate, formparanate hloride, fosmethilan, fospirate, fosthietan, furathiocarb,
furethrin, gamma-cyhalothrin, gamma-HCH, halfenprox, halofenozide, HCH, HEOD, hlor,
heptafluthrin, heptenophos, heterophos, hexaflumuron, HHDN, hydramethylnon, hydrogen cyanide,
hydroprene, hyquincarb, imidacloprid, imiprothrin, indoxacarb, iodomethane, IPSP, isazofos,
isobenzan, isocarbophos, isodrin, isofenphos, isofenphos-methyl, isoprocarb, isoprothiolane,
isothioate, isoxathion, ivermectin, jasmolin I, jasmolin II, jodfenphos, juvenile hormone I, juvenile
hormone II, juvenile hormone III, kappa-bifenthrin, kappa-tefluthrin, n, kinoprene, lambda-
cyhalothrin, lead arsenate, lepimectin, leptophos, lindane, os, lufenuron, lythidathion,
malathion, malonoben, mazidox, mecarbam, mecarphon, menazon, mephosfolan, mercurous
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
chloride, mesulfenfos, metaflumizone, methacrifos, methamidophos, methidathion, methiocarb,
methocrotophos, methomyl, methoprene, ychlor, methoxyfenozide, methyl e, methyl
isothiocyanate, methylchloroform, ene chloride, metofluthrin, metolcarb, metoxadiazone,
mevinphos, mexacarbate, milbemectin, milbemycin oxime, mipafox, mirex, molosultap,
momfluorothrin, monocrotophos, hypo, monosultap, morphothion, moxidectin, naftalofos,
naled, naphthalene, nicotine, nifluridide, nitenpyram, nithiazine, nitrilacarb, novaluron,
noviflumuron, omethoate, oxamyl, oxydemeton-methyl, oxydeprofos, oxydisulfoton, paradichlorobenzene
, parathion, ion-methyl, penfluron, pentachlorophenol, permethrin,
phenkapton, phenothrin, oate, phorate, phosalone, phosfolan, phosmet, phosnichlor,
phosphamidon, phosphine, phoxim, phoxim-methyl, pirimetaphos, pirimicarb, pirimiphos-ethyl,
pirimiphos-methyl, potassium arsenite, potassium thiocyanate, pp'-DDT, prallethrin, ene I,
precocene II, precocene III, primidophos, profenofos, profluralin, promacyl, promecarb, propaphos,
propetamphos, propoxur, dathion, ofos, ate, protrifenbute, pyflubumide,
pyraclofos, pyrafluprole, pyrazophos, ethrin, pyrethrin I, pyrethrin II, pyrethrins, pyridaben,
pyridalyl, pyridaphenthion, pyrifluquinazon, pyrimidifen, pyriminostrobin, tate, pyriprole,
oxyfen, quassia, quinalphos, phos-methyl, quinothion, rafoxanide, resmethrin, rotenone,
ryania, sabadilla, schradan, selamectin, silafluofen, silica gel, sodium arsenite, sodium de,
sodium hexafluorosilicate, sodium thiocyanate, sophamide, spinetoram, spinosad, spiromesifen,
spirotetramat, sulcofuron, sulcofuron-sodium, sulfluramid, sulfotep, sulfoxaflor, sulfuryl fluoride,
sulprofos, tau-fluvalinate, tazimcarb, TDE, tebufenozide, tebufenpyrad, tebupirimfos,
teflubenzuron, hrin, temephos, TEPP, terallethrin, terbufos, tetrachloroethane,
tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole, theta-cypermethrin, thiacloprid,
thiamethoxam, thicrofos, thiocarboxime, thiocyclam, clam oxalate, thiodicarb, thiofanox,
thiometon, thiosultap, thiosultap-disodium, thiosultap-monosodium, thuringiensin, tioxazafen,
tolfenpyrad, tralomethrin, transfluthrin, transpermethrin, thene, triazamate, triazophos,
trichlorfon, trichlormetaphos-3, trichloronat, trifenofos, triflumezopyrim, triflumuron, trimethacarb,
ne, thion, vaniliprole, XMC, xylylcarb, zeta-cypermethrin, zolaprofos, and any
combinations thereof.
Additionally, the compounds described herein may be combined with herbicides that
are compatible with the compounds of the present disclosure in the medium selected for application,
and not nistic to the activity of the present compounds to form pesticidal mixtures and
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
synergistic mixtures thereof The fungicidal compounds of the present disclosure may be applied in
conjunction with one or more herbicides to control a wide variety of undesirable plants. When used
in conjunction with herbicides, the presently claimed compounds may be formulated with the
ide(s), tank-mixed with the ide(s) or applied sequentially with the herbicide(s). Typical
herbicides include, but are not limited to 4-CPA, 4-CPB; 4-CPP; 2,4-D; 3,4-DA; 2,4-DB; 3,4-DB;
2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen,
in, alachlor, allidochlor, alloxydim, ally] alcohol, alorac, dione, ametryn, amibuzin,
amicarbazone, amidosulfuron, yclopyrachlor, aminopyralid, amiprofos-methyl, amitrole,
ammonium ate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron,
tryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate,
bensulfuron, bensulide, bentazone, benzadox, benzfendizone, benzipram, benzobicyclon,
benzofenap, benzofluor, benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos, bispyribac,
borax, bromacil, onil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor,
butafenacil, butamifos, butenachlor, buthidazole, buthiuron, in, butroxydim, n, butylate,
cacodylic acid, cafenstrole, calcium te, m cyanamide, cambendichlor, carbasulam,
carbetamicle, carboxazole, chlorprocarb, cait'entrazone, CDEA, CEPC, chlomethoxyfen,
chloramben, chloranocryl, zifop, chlorazine, chlorbromuron, chlorbufam, chloreturon,
chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen,
chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal,
hiamid, cinidon-ethyl, cinmethylin, lfuron, cisanilide, clethoclim, cliodinate, clodinafop,
clofop, one, clomeprop, cloprop, cloproxydim, alid, cloransulam, CMA, copper
sulfate, CPNJF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate,
cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyperquat, cyprazine,
cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate,
dicamba, benil, ralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop, diclosulam,
diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, enican, diflufenzopyr,
dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P,
dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid,
dipropetryn, diquat, disul, dithiopyr, , DMPA, DNOC, DSMA, EBEP, eglinazine, endothal,
epronaz, EPTC, erbon, esprocarb,ethalfluralin, ethametsulfuron, ethidimuron, ethiolate,
ethofumesate,ethoxyfen, ethoxysulfuron, etinofen, etnipromid, zanid, EXD, fenasulam,
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
fenoprop, fenoxaprop, fenoxaprop-P, fenmasulfone, notrione, fenteracol, fenthiaprop,
fentrazamide, fenuron, ferrous sulfate, op, flamprop-M, flazasulfuron, florasulam, fluazifop,
fluazifop-P, fluazolate, flucarbazone, flucetosulfuron, oralin, flufenacet, flufenican, flufenpyr,
flumetsulam, flumezin, flumiclorac, xazin, flumipropyn, fluometuron, fluorodifen,
fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, panate,
flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fen,
foramsulfuron, fosamine, x:yfen, glufosinate, glufosinate-P, glyphosate, halauxifen, halosafen,
halosulfuron, haloxydine, haloxyfop, haloxyfop-P, hexachloroacetone, hexaflurate, hexazinone,
imazamethabenz, imazamox, imazapic, yr, imazaquin, imazethapyr, ulfuron,
indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iofensulfuron, ioxynil, ipazine,
ipfencarbazone, iprymidam, isocarbamid, , isomethiozin, isonoruron, isopolinate, isopropalin,
isoproturon, isouron, isoxaben, isoxachl011ole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox,
lactofen, lenacil, linuron, MAA, MAMA, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop
P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop,
metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin,
methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide,
methyl ocyanate, methyldymron, metobenzuron, metobromuron, chlor, metosulam,
ron, metribuzin, metsulfuron, molinate, monalide, monisouron, monochloroacetic acid,
monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, napropamide-M,
naptalam, neburon, nicosulfuron, clofen, nitralin, nitrofen, nitrofluorfen, razon,
noruron, OCH, orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl,
oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, parafluron, paraquat, pebulate,
pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, azone,
perfluidone, amid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron,
mercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium
azide, potassium e, pretilachlor, primisulfuron, procyazine, prodiamine, profluazol,
profluralin, profoxydim, proglinazine, prometon, prometryn, propachlor, propanil, propaquizafop,
propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin,
prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, ufen, pyrasulfotole,
pyrazolynate, pyrazosulfuron, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol,
pyridate, alid, pyriminobac, sulfan, pyrithiobac, pyroxasulfone, pyroxsulam, quinclorac,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
quinmerac, quinoclamine, amid, quizalofop, quizalofop-P, rhodethanil, rimsulfuron,
saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, n,
simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate,
sulfentrazone, eturon, sulfosulfuron, sulfuric acid, sulglycapin, swep, TCA, tebutam,
tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,
terbuthylazine, ryn, tetrafluron, thenylchlor, thiazafluron, pyr, thidiazimin, thidiazuron,
thiencarbazone-methyl, thifensulfuron, thiobencarb, tiafenacil, tiocarbazil, tioclorim, tolpyralate,
topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tricamba,
triclopyr, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, sulfuron, trifop,
l O trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, ate, and
xylachlor.
[0043J Another embodiment of the t disclosure is a method for the control or
prevention of fungal attack. This method comprises ng to the soil, plant, roots, foliage, or
locus of the fungus, or to a locus in which the infestation is to be prevented (for example applying to
cereal or grape plants), a fungicidally effective amount of one or more of the compounds of Formula
L The compounds are suitable for treatment of various plants at fungicidal levels, while exhibiting
low oxicity. The compounds may be useful both in a protectant and/or an eradicant fashion.
100441 The compounds have been found to have significant fungicidal effect particularly for
agricultural use. Many of the compounds are particularly ive for use with agricultural crops
and horticulturalplants.
[0045J It will be understood by those skilled in the art that the efficacy of the compound for
the foregoing fungi establishes the general utility of the compounds as ides.
[0046J The compounds have broad ranges of activity against fungal pathogens. Exemplary
ens may include, but are not limited to, causing agent of wheat leaf blotch (Zymoseptoria
lritic.:i), wheat brown rust (Puu.:inia tritil:ina), wheat stripe rust inia slriiformis), scab of apple
(Venturia inaequalis), powdery mildew of grapevine (Uncinula necator), barley scald
(Rhynchosporium secalis), blast of rice (Pyricularia oryzae), rust of soybean (Phakopsora
pachyrhizi), glume blotch of wheat (Leptosphaeria nod.arum), powdery mildew of wheat (Blumeria
isf sp.tritici), powdery mildew of barley (Blumeria graminisf sp. hordei), powdery mildew
of cucurbits (Erysiphe cichoracearum), anthracnose of cucurbits (Colletotrichum lagenarium), leaf
spot of beet spora beticola), early blight of tomato (Alternaria solani), and spot blotch of
[Annotation] an
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ation] Mel.Chan
Unmarked set by Mel.Chan
barley (Cochlioho/11s .,ativ11.\) The exact amount of the active material to be applied is dependent
not only on the specific active material being applied, but also on the particular action d, the
fungal species to be lled, and the stage ofgrmvth thereof as well as the part of the plant or
other t to be contacted with the compound. Thus, all the compounds, and ations
ning the same, may not be equally effective at similar concentrations or against the same
fungal species.
[00471 The compounds are effective in use with plants in a disease-inhibiting and
phytologically acceptable amount The term "disease-inhibiting and phytologically acceptable
amount" refers to an amount of a compound that kills or inhibits the plant disease for which control
l 0 is desired, but is not icant!y toxic to the plant This amount will generally be from about 0.1 to
about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of
compound required varies with the fungal disease to be controlled, the type offormulation
employed, the method of application, the particular plant species, climate conditions, and the like. A
le application rate is typically in the range from about O IO to about 4 pounds/acre (about O O I
to 0.45 grams per square meter, g/m2).
100481 Any range or desired value given herein may be e:--;tended or altered without losing the
effects sought, as is apparent to the skilled person for an understanding ofthe teachings herein.
100491 The compounds ofFormula I may be made using well-known chemical procedures.
Intermediates not specifically mentioned in this disclosure are either cially available, may
be made by routes disclosed in the chemical literature, or may be readily synthesized from
commercial starting materials utilizing standard procedures.
GENERAL SCHEMES
[00501 The following schemes rate approaches to generating picolinamide compounds
of Formula L The following descriptions and examples are provided for rative purposes and
should not be construed as limiting in terms of substituents or substitution patterns.
Compounds of Formula 1.1, wherein R3 and R12 are as originally defined and are
equivalent, can be prepared by the methods shown in Scheme 1, step a. The compound of
Formula 1.0 can be treated with an organometallic nucleophile such as phenylmagnesium
bromide (PhMgBr) in a polar aprotic solvent such as tetrahydrofuran (THF) at a temperature of
[Annotation] Mel.Chan
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[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
about 0 °C to 23 °C to afford compounds of Formula 1.1, Vvherein R1 and R12 are as previously
defined, as shown in a.
Scheme 1
CH3 CH3
?0 ------>-
(PMB)Bno (PMS)BnO?:?
OEt R3
1.0 1 .1
100521 Compounds of Formula 2.2, wherein R, is as ally defined and may or may not
be equal to R12, can be prepared by the methods shown in Scheme2, steps a - c. Compounds of
a 2.2, wherein R3 and R12 are as previously defined but not an electron-deficient aryl or
heteroaryl group and may or may not be equivalent, can be obtained by treating the nds
of a 2.0, wherein R, and R12 are as previously defined but not an electron-deficient aryl or
heteroaryl group and may or may not be equivalent, with a mixture of a hydride reagent, such as
triethylsilane (Et3SiH), and an acid, such as 2,2,2-trifluoroacetic acid (TFA) in a halogenated
solvent such as dichloromethane (DCM) at a temperature of about 0 °C to 23 °C, as depicted in
a. Alternatively, compounds of Formula 2.1, wherein R3 and R12 are an electron-deficientaryl or
heteroaryl group and may or may not be equivalent, can be obtained by treating the compounds
of a 2.0, wherein R3 and R12 are an electron-deficient aryl or heteroaryl group and may or
may not be equivalent, with a base, such as sodium hydride (NaH), and a st, such as
imidazole, in a polar aprotic t such as THF at a temperature of about 23 °C, followed by
sequential addition of carbon disulfide (CS2) and an alkyl iodide, such as thane (I\IeI), as
depicted in b. Compounds of Formula 2.2, wherein R3 and R12 are an electron-deficient aryl or
heteroaryl group and may or may not be equivalent, can be obtained by treating the compounds
of Formula 2.1, wherein R3 and R12 are as previously defined and may or may not be equivalent,
with a tin reagent, such as tributyltin hydride, and a radical initiator, such as
azobisisobutyronitrile (AIBN), in a nonpolar t such as toluene at a temperature of about
115 °C, as ed inc.
Scheme2
[Annotation] Mel.Chan
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Unmarked set by Mel.Chan
(0053] Compounds of Formula 3. I, wherein R, and R12 are as originally defined and may
or may not be equivalent, can be prepared according to the method outlined in Scheme 3, step a.
Compounds of Formula 3.1, wherein R1 and R 12 are as originally defined and may or may not be
equivalent, can be prepared from nds of Formula 3.0, wherein R3 and R12 are as
previously defined and may or may not be lent, by ng with a base, such as NaH and
an alkyl halide, such as Mel, in a polar aprotic solvent like N,N-dimethylformamide (DMF) at a
temperature of about O °C to 23 °C, as depicted in a.
Scheme 3
_,,l a
? R12
(PMB) BnO
, ?OH
Compounds of Formula 4.1, wherein R3 and R12 are as originally defined and may
or may not be equivalent, can be prepared according to the method outlined in Scheme 4, step a.
Compounds of Formula 4.1, wherein R3 and R12 are as originally d and may or may not be
equivalent, can be prepared from compounds of Formula 4.0, wherein R3 and R12 are as
previously defined and may or may not be equivalent, by treating with a fluorination reagent,
such as (diethylamino)sulfur trifluoride (DAST), in a nated solvent such as DCM at a
temperature of about O °C to 23 °C, as depicted in a.
[Annotation] an
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Scheme 4
Bn0?=12
(00551 Compounds of Formula 5.3, wherein R3, R4, and R12 are as originally defined and
R3 may or may not be equivalent to R12, can be prepared ing to the methods outlined in
Scheme 5, steps a - c. Compounds of Formula 5.3, wherein R1, R4, and R 12 are as originally
defined and R3 may or may not be equivalent to R12, can be prepared from compounds of
a 5.0, wherein R1, R4, and R12 are as originally defined and R, may or may not be
equivalent to R12, by treating with a catalyst such as palladium on carbon (Pd/C) in a e of
an unsaturated hydrocarbon solvent, such as cyclohexene, and a polar protic solvent, such as
ethanol (EtOH), at an elevated temperature of about 65 °C, as shown in a. Alternatively,
compounds of Formula 5.3, wherein R3 and R12 are an electron-deficient aryl or heteroaryl group
and may or may not be equivalent and R4 is hydroxyl (OH) or alkoxy, can be obtained by
treating nds of Formula 5.1, wherein R3,?, and R12 are as previously defined and R3
may or may not be equivalent to R12, with a mixture of a hydride reagent, such as Et1SiH, and an
acid, such as TFA in a halogenated solvent such as DCM at a temperature of about O °C to 23
°C, as indicated in h. Additionally, compounds of Formula 5.3, wherein R1 and R12 are as
originally defined but not an electron-deficient aryl or heteroaryl group and may or may not be
equivalent, and? is a proton (H), can be obtained by treating the nds of Formula 5.2,
n R3, R4, and R12 are as previously defined and R3 may or may not be equivalent to R12,
with a mixture of a e reagent, such as Et3SiH, and an acid, such as TFA in a halogenated
t such as DCM at a temperature of about O °C to 23 °C, as depicted in c.
Scheme 5
[Annotation] Mel.Chan
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[Annotation] an
Unmarked set by Mel.Chan
CH3 CH3 CH3
BnO?R 12
PMBO?R PMBO?R12
R4 R4 OH
R3 R3 R3
.0 5.1 5.2
a b C
Compounds of Formula 6.2, wherein R3 and R12 are an electron-deficient aryl or
heteroaryl group and equivalent, can be prepared ing to the methods outlined in Scheme 6,
steps a -b. Compounds of Formula 6.1, wherein R3 and R12 are as described previously, can be
prepared from compound of Formula 6.0, by treating with an aryl bromide, such as 4-
bromobenzonitrile, in the presence of a Pd catalyst, such as XPhos Pd G3 (CAS # 14450851
commercially available from Sigma-Aldrich), in a polar aprotic solvent such as THF at a
IO temperature of about 55 °C, as ted in a Compounds of Formula 6.2, wherein R1 and R 12
are as described previously, can be prepared from compound of Formula 6.1, wherein R3 and R12
are as described previously, by treating with a hydride reagent, such as borane yl sulfide
complex, in the presence of a catalyst, such as (R)-(+)Methyl-CBS-oxazaborolidine, in a polar
protic solvent, such as methanol (MeOH), at a temperature of about O °C, as indicated in b.
Scheme 6
0 CH3
A0 a b
R12 R12
H3CAy HO?
H3C CH3
R3 R3
6.0 6.1 6.2
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[Annotation] Mel.Chan
Unmarked set by an
Compounds of Formula 7.2, wherein R3 and R12 are as originally defined and
equivalent, can be prepared according to the methods outlined in Scheme 7, steps a - h.
Compounds of Formula 7.1, wherein R3 and R12 are as described usly, can be prepared
from compounds of Formula 7.0, by treating with a catalyst, such as SbCls, in a halogenated
t such as DCM at a temperature of about 23 °C, as indicated in a. Compounds of Formula
7.2, wherein R, and R 12 are as described previously, can be prepared from compound ofFormula
7.1, n R3 and R12 are as described previously, by treating with a hydride reagent, such as
borane dimethyl sulfide complex, in the presence of a catalyst, such as (R)-(+)Methyl-CBS-
oxazaborolidine, in a polar protic solvent, such as methanol (MeOH), at a temperature of about
23 °C, as ted in b.
Scheme 7
OH 0 CH3
H3C a b
?R12 ?R12 ?R12
R3 HC3 HO
CH3 CH3 CH3
OH R3 R3
7.0 7.1 7.2
[0058J Compounds of Formula 8.1, wherein n is either 0 or 1, and Wis either CH2 or 0,
can be prepared according to the method outlined in Scheme 8, step a. Compounds of Formula
8.1, wherein n is either O or I, and Wis either CH2 or 0, can be prepared from compounds of
Formula 8.0, wherein n is either 0 or 1, and Wis either CH2 or 0, by treating with a base, such as
yllithium Li), and an aldehyde, such as acetaldehyde, in a polar aprotic solvent such
as THF at a temperature of about -78 °C to 23 °C, as indicated in a.
Scheme 8
a HO
[Annotation] Mel.Chan
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[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Compounds of Formula 9.1, n R3 and R12 are as originally defined, can be
prepared according to the method outlined in Scheme 9, step a. Compounds of Formula 9.1,
wherein R3 and R12 are as originally defined, can be prepared from compounds of a 9.0,
wherein R,is as originally defined (Formula 9.0 is either commerically available, or could be
prepared from asymmetric Shi epoxidation of the corresponding £-olefin precursor, as reported
in Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R: Shi, Y. .! Am. ('hem. Soc. 1997, I 19, 11224),
by treating with a pre-mixed suspension of a copper(!) salt, such as copper iodide (Cul), and an
organometallic nucleophile, such as 4-(trifluoromethyl)phenylmagnesium bromide in a polar
aprotic solvent such as THF, at a temperature of about -78 °C to 23 °C, as shown in a.
Scheme 9
.,,,R12
9.0 9.1
[0060] nds of Formula 10.2, n R1, R2, R3, R4 and R12 are as originally
d, can be prepared according to the method outlined in Scheme 10, step a Compounds of
Formula 10.0, wherein R1 is as originally d, can be treated with ls of Formula 10.1,
wherein R2, R3, R-1 and R 12 are as originally defined, and a coupling reagent such as 3-
(ethyliminomethyleneamino)-N,N-dimethylpropanamine hydrochloride (EDC), and a catalyst
such as N,N-dimethylpyridinamine (DMAP) in a halogenated solvent like DCM to afford
compounds of Formula 10.2, wherein R1, R2, R3, R-i and R12 are as previously defined, as shown
1n ll.
Scheme 10
+ ,,. R12 -a
HO.A,
- 'f-R4
10.0 10.1
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[Annotation] Mel.Chan
Unmarked set by Mel.Chan
10061 J Compounds of Formula 11.2, wherein R1, R2, R,, R4, Re" R12 and Z are as ally
defined, can be prepared according to the methods outlined in Scheme 11, steps a - b. As
ed in a, compounds of Formula 11.2, wherein R 1, R2, R1, R4 and R12 are as ally
defined, can be subjected to an acid, such as a 4 normal (N) on of hydrogen chloride (HCl)
in dioxane, in a halogenated solvent such as DCM to afford compounds of Formula 9.0, \vherein
R1, R2, R3, ? and R12 are as originally defined, as shown in a.
[00621 Compounds of Formula 11 0, wherein R1, R2, R1, R4 and R12 are as originally
defined, can be treated with compounds of Formula 11.1, n R6 and Z are as originally
defined, in the presence of a base, such as diisopropylethylamine ), and a peptide
l O coupling reagent, such as benzotriazolyl-oxytripyrrolidinophosphonium hexafluorophosphate
(PyBOP), in an halogenated solvent like DCM, to afford compounds of Formula 11.2, wherein
R,, R2, R,, R4, Re,, R12 and Z are as originally defined, as shown in b.
Scheme 11
?z?OH 11.2
11.1
Compounds of a 12.0, wherein R1, R2, R3, ?' &,, R7, R12 and Z are as
originally defined, can be prepared according to the method outlined in Scheme 12, step a. As
shown in a, compounds of Formula 11.2, wherein R1, R2, R3, R4, R6, R12 and Z are as originally
defined, can be treated with an appropriate alkyl halide with or without a reagent such as sodium
iodide (Nal) and an alkali carbonate base, such as sodium carbonate (Na2C03) or potassium
1002106834
carbonate (K2CO3), in a solvent like acetone at a temperature of about 55 °C, or by treatment
with an acyl halide in the presence of an amine base, such as pyridine, ylamine (Et3N),
DMAP, or mixtures thereof, in an aprotic solvent such as DCM, at a temperature of about 23
°C, to afford compounds of Formula 12.0 wherein R1, R2, R3, ?, ?, R7, R12 and Z are as
originally defined.
Scheme 12
- IY6
Rs R7
o R2
a ?::2
0 R1 R3
11.2 12.0
EXAMPLES
[0064) The chemistry in the following examples may be conducted using either
enantiomer of2-((tert-butoxycarbonyl)amino)propanoic acid (Boe-Ala-OH) or either protected
(PMB or Bn) or ected enantiomer ofethyl lactate.
[0065] Example 1: Preparation of (S)(benzyloxy)- l,1-bis(4-fluorophenyl)propan
- BnO
[0066) To a solution of (S)-ethyl2-(benzyloxy)propanoate (2.08 grams (g), 10.0
millimoles (mmol)) in ydrofuran (THF; 20 milliliters (mL)) at O °C was slowly added (4-
fluorophenyl)magnesium bromide (31.3 mL, 25.0 mmol, 0.8 molar (M) in THF) over a 10 minute
(min) period. The reaction vessel was d to warm slowly to room temperature over 2 hours
(h), and the reaction mixture was quenched by careful addition of ted (sat.) aqueous (aq.)
ammonium chloride (N?Cl; 50 mL). The mixture was diluted with diethyl ether (Et2O; 50 mL),
1002106834
the phases were separated, and the aq. phase was extracted with Et2O (2 x 50 mL). The combined
organic phases were washed with sat. aq. sodium chloride (NaCl, brine; 100 mL), dried over
sodium sulfate (Na2SO4), filtered, and concentrated. The resulting oil was purified by flash column
chromatography (silica gel (SiO2), O?5% acetone in hexanes) to afford the title compound (3.28 g,
93%) as a colorless oil: 1H NMR (300 MHz, CDCh) 8 7.47- 7.38 (m, 2H), 7.38 -7.27 (m, 5H),
7.17-7.09 (m, 04-6.89 (m, 4H), 4.64 (dd, J= 11.4, 0.7 Hz, lH), 4.51-4.38 (m, 2H), 3.12
(s, lH), 1.11 (d, J= 6.1 Hz, 3H); 19FNMR (376 MHz, CDCh) 8 -116.19, -116.41; ESIMS m/z 377
([M+Nat).
[0067] Example 2A: Preparation of (S)-4,4'-(2-(benzyloxy)propane-l,1-
diyl)bis(fluorobenzene).
F F
BnO - BnO
F F
To a solution of (S)(benzyloxy)-1,1-bis(4-fluorophenyl)propanol (709
rams (mg), 2.00 mmol) in dichloromethane (DCM; 20 mL) at O °C was added triethylsilane
(Et3SiH; 3.19 mL, 20.0 mmol) followed by 2,2,2-trifluoroacetic acid (TFA; 1.53 mL, 20.0 mmol).
The mixture was stirred at O °C for 1 h. The resulting on was quenched by careful on of
sat. aq. sodium bicarbonate (NaHCO3; 20 mL). The phases were separated, and the aq. phase was
extracted with DCM (2 x 30 mL). The combined organic phases were washed with brine (50 mL),
dried over , filtered, and concentrated. The resulting oil was ed by flash column
chromatography (Si 02, o? 10% acetone in hexanes) to afford the title compound (627 mg, 92%) as
a white solid: 1H NMR (400 MHz, CDCb) 8 7.31- 7.22 (m, 5H), 7.21-7.16 (m, 2H), 7.10-7.03
(m, 2H), 7.00-6.91 (m, 4H), 4.54 (dd, J= 11.5, 0.7 Hz, 1H), 4.31 (dd,J= 11.6, 0.8 Hz, lH), 4.14
(dq, J= 8.1, 6.1 Hz, IH), 3.93 (d, J= 8.1 Hz, lH), 1.18 (d, J= 6.0 Hz, 3H); 19FNMR (376 MHz,
CDCh) 60, -117.10; ESIMS (m/z) 361 ([M+Nat).
Example 2B: Preparation of (S)-(2-(benzyloxy)-l -methoxypropane-1,1-
diyl)dibenzene.
1002106834
BnO - BnO
To a suspension of sodium hydride (NaH; 52.0 mg, 1.30 mmol, 60% weight per
weight (w/w) in mineral oil) inN,N-dimethylformamide (DMF; 3 mL) at 0 °C was added a solution
of(S)(benzyloxy)-l,l-diphenylpropanol (318 mg, 1 mmol) in DMF (1 mL). The reaction
mixture was stirred at room temperature for 30 min and then cooled to O 0C. Iodomethane (Mel;
93.0 iters (µL), 1.50 mmol) was added, and the on mixture was stirred at room
temperature for l h. The resulting solution was quenched by careful addition of sat. aq. NaHCO3
(10 mL). The mixture was diluted with diethyl ether (Et2O; 10 mL), the phases were separated, and
the aq. phase was extracted with Et2O (2 x 10 mL). The combined organic phases were washed
with brine (20 mL), dried over Na2SO4, filtered, and concentrated. The resulting oil was purified by
flash column chromatography (SiO2, 0?5% acetone in hexanes) to afford the title compound (295
mg, 89%) as a colorless oil: 1H NMR (400 MHz, CDCh) 87.47- 7.41(m, 2H), 7.40- 7.35 (m,
2H), 7.33- 7.18 (m, llH), 4.69 (d,J= 11.9 Hz, lH), 4.54 (d,J= 12.3 Hz, lH), 4.50 (q, J= 6.1 Hz,
lH), 3.13 (s, 3H), 1.10 (d,J= 6.1 Hz, 3H); 13CNMR(l01 MHz, CDCh) 8142.96, 141.31, 138.79,
, 128.54, 128.14, 127.61, , 127.08, 126.95, 126.69, 99.99, 85.35, 78.13, 70.80, 52.46,
13.65; ESIMS (mlz) 333 ([M+Ht).
[0071] e 2C: Preparation of (S)-(2-(benzyloxy)-l-fluoropropane-l,1-
diyl)dibenzene.
BnO - BnO
To a solution of (benzyloxy)-l,l-diphenylpropanol (300 mg, 0.942
mmol) in DCM (5 mL) at O °C was added (diethylamino)sulfur trifluoride (DAST; 1.88 mL, 1.88
mmol, 1 Min DCM). The reaction was slowly warmed to room temperature over 3 h. The resulting
1002106834
solution was quenched by careful addition of sat. aq. NaHCO3 (5 mL). The phases were separated,
and the aq. phase was extracted with DCM (2 x 10 mL). The combined organic phases were
washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated. The resulting oil was
purified by flash column chromatography (SiO2, O?10% acetone in hexanes) to afford the title
compound (300 mg, 98%) as a colorless oil: 1H NMR (400 MHz, CDC'3) 87.58-7.49 (m, 2H),
7.43-7.37 (m, 2H), 7.36-7.20 (m, 9H), 7.09-6.99 (m, 2H), 4.47 (d, J= 11.7 Hz, lH), 4.37-
4.25 (m, 2H), 1.26 (dd,J= 6.3, 1.3 Hz, 3H); 13C NMR (101 MHz, CDC13) 8 142.23 (d, J= 22.7
Hz), 141.00 (d,J= 23.5Hz), 138.03, 128.21, 128.16, 127.90 (d, J= 1.5 Hz), 127.80, 127.72 (d, J=
1.7 Hz), 127.52, 127.42 (d,J= 1.3 Hz), 126.23 (d,J= 9.6 Hz), 125.93 (d,J= 8.7 Hz), 99.96 (d,J=
180.8Hz), 78.91 (d,J= ), 71.68, 14.47 (d,J= 3.6Hz); 19FNMR(376 MHz,CDCh)8-
159.80.
Example 2D, Step 1: Preparation of(S)-O-(2-(benzyloxy)-l,l-bis(3,4,5-
trifluorophenyl)propyl) yl carbonodithioate.
F F
BnO F BnO
F F
F F
To a solution of (S)(benzyloxy)-l, l-bis(3,4,5-trifluorophenyl)propanol
(496 mg, 1.16 mmol) in anhydrous THF (5.8 mL) was added NaH (93.0 mg, 2.33 mmol), followed
by ole (3.96 mg, 0.0580 mmol), and the reaction mixture was stirred at ambient temperature
for 1 h. Carbon disulfide (562 µL, 9.30 mmol) was added via syringe in one portion, followed by
Mel (579 µL, 9.30 mmol), and the reaction mixture was stirred at ambeint ature for 2 h. The
reaction mixture was diluted with Et2O (5 mL) and quenched with sat. aq. NH4Cl (10 mL). The
layers were separated, and the aq. layer was ted with Et2O (3 x 10 mL). The ed
organic layers were dried over magnesium sulfate (MgSO4), filtered and concentrated to afford an
orange/brown oil. The crude oil was purified by flash column tography (SiO2, 0?50% ethyl
acetate (EtOAc) in hexanes) to afford the title nd (627 mg, 94%) as a clear, bright yellow
colored oil: 1H NMR (400 MHz, CDC'3) 8 7.40-7.27 (m, 3H), 7.24-7.16 (m, 2H), 7.02 (dd, J=
[Annotation] Mel.Chan
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[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
1002106834
9.1, 6.6 Hz, 2H), 6.96 (dd, J=8.8, 6.5 Hz, 2H), 5.44 (q, J= 6.1 Hz, lH), 4.66 (d, J= 11.6 Hz, lH),
4.51 (d, J= 11.6 Hz, lH), 2.49 (s, 3H), 1.16 (d, J= 6.1 Hz, F NMR (376 MHz, CDCb) 8-
133.89 (d, J= 20.7 Hz), -134.73 (d, J= 20.6 Hz), -159.83 (t,J= 20.6 Hz), -160.56 (t, J= 20.7 Hz);
(Thin film) 2922, 1721, 1622, 1595, 1526, 1436, 1344, 1241, 1217, 1197, 1119, 1088, 1040, 965,
908,861, 822, 730, 712, 697, 672 cm-1•
e 2D, Step 2: Preparation of (S)-5,5'-(2-(benzyloxy)propane-1,1-
diyl)bis(1,2,3-trifluorobenzene).
F F
BnO BnO F
F F
F
A solution of(S)-O-(2-(benzyloxy)-1,1-bis(3,4,5-trifluorophenyl)propyl) S-
methyl carbonodithioate (598 mg, 1.16 mmol) in toluene (200 mL) was degassed by a freezepump-thaw
procedure (3 cycles using liquid nitrogen (N2)) under an here ofN2• Tributyltin
e (3.12 mL, 11.6 mmol) was then added, the reaction flask was fitted with a reflux condenser,
and the reaction mixture was heated to a light reflux (115 °C). A solution ofazobisisobutyronitrile
(AIBN; 0.200 g, 1.22 mr..101) in degassed toluene (3 cycles via liquidN2; 32 mL) was added via
syringe down the reflux condenser over 3 h. Once slow addition ofthe AIBN was te, the
reaction e was stirred at reflux overnight. The solvent was removed in vacuo to provide a
pale yellow oil. The crude oil was purified by flash column chromatography (SiO2, 0?30% EtOAc
in hexanes) to afford the title compound (358 mg, 72%) as a clear, colorless oil:1H NMR ( 400
MHz, CDCb) 8 7.28 (d,J= 6.6 Hz, 3H), 7.17 - 7.06 (m, 2H), 6.92 (dd, J= 8.5, 6.5 Hz, 2H), 6.79
(dd,J= 8.3, 6.4 Hz, 2H), 4.59 (d, J= 11.7 Hz, lH), 4.31 (d, J= 11.7 Hz, lH), 4.02 (p, J= 6.2 Hz,
lH), 3.76 (d,J= 6.8 Hz, lH), 1.19 (d, J= 6.1 Hz, 3H);19F NMR (376 MHz, CDCb) 8-133.80 (d, J
= 20.5 Hz),
-134.34 (d, J= 20.5 Hz), -162.54 (t,J= 20.5 Hz), -162.84 (t, J= 20.5 Hz); (Thin film) 2871, 1621,
1526, 1445, 1345, 1262, 1235, 1116, 1096, 1043, 859,802, 728, 698, 679 cm-1•
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
1002106834
e 3A: Preparation of (S)-1, I-bis(4-fluorophenyl)propanol.
F F
BnO HO
F F
[0078] To a solution of(S)-4,4'-(2-(benzyloxy)propane-l,1-diyl)bis(fluorobenzene)
(575 mg, 1.70 mmol) in ethanol (EtOH; 11 mL) and cyclohexene (5.5 mL) at room temperature
was added palladium on carbon (Pd/C; 362 mg, 0.0850 mmol, 2.5% w/w ofPd). The reaction
mixture was stirred at 65 °C for 2 h, cooled to room temperature, ed through a plug of Celite®,
and concentrated to afford the title compound (415 mg, 98%) as a colorless oil: 1H NMR (400
MHz, CDC'3) 8 7.36-7.29 (m, 2H), .18 (m, 2H), 7.09-6.93 (m, 4H), 4.47 (dqd, J= 8.2,
6.1, 3.3 Hz, IH), 3.80 (d, J= 8.3 Hz, IH), 1.55 (d, J= 3.3 Hz, IH), 1.19 (d, J= 6.1 Hz, 3H); 13C
NMR (101 MHz, CDC'3) 8162.90 (d, J= 23.3 Hz), 160.46 (d, J= 23.1 Hz), 138.15 (d, J= 3.1 Hz),
136.94 (d, J= 3.6 Hz), 130.14 (d, J= 7.8 Hz), 129.55 (d,J= 7.8 Hz), 115.70 (d,J= 18.8 Hz),
115.49 (d, J= 18.8 Hz), 70.07, 58.61, 21.63; 19F NMR (376 MHz, CDC'
3) 8-115.84, -116.19.
Example 3B: Preparation 1,1-bis(2-fluorophenyl)propane-1,2-diol.
To a solution of (S)-1,1-bis(2-fluorophenyl)((4-methoxybenzyl)oxy)propan-
1-ol (790 mg, 2.06 mmol) in DCM (20 mL) at O °C was added Et3SiH (3.28 mL, 20.6 mmol)
followed by TFA (1.57 mL, 20.6 mmol). The mixture was stirred at O °C for 1 h. The resulting
solution was quenched by careful addition of sat. aq. NaHCO3 (20 mL). The phases were separated,
and the aq. phase was extracted with DCM (2 x 30 mL). The combined organic phases were
washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. The ing oil was
purified by flash column chromatography (Si02, O?10% acetone in hexanes) to afford the title
1002106834
nd (388 mg,71%) as a colorless oil:1H NMR (400 MHz,CDCh)o 7.90- 7.77 (m,lH),
7.70 (tt,J= 8.2,1.5 Hz,lH),7.31- 7.10 (m,4H),6.97 (ddd,J= 12.7,8.1,1.3 Hz,IH),6.88 (ddd,J
=11.8,8.0,1.4 Hz,lH),5.11 (qd,J= 6.3,2.3 Hz,lH),3.49 (s,lH),2.27 (s,1H),1.09 (d,J= 6.3
Hz,3H); 19F NMR (376 MHz,CDC1 = 8.3 Hz),-113.92 (d,J= 8.4 Hz); ESIMS
3) o -112.90 (d,J
(m/z) 551 ([2M+Nat).
e 3C: Preparation of(S)-1,1-bis(4-bromophenyl)propanol.
Br Br
PMBO - HO
Br Br
[0082] To a solution of (S)-1,1-bis(4-bromophenyl)((4-methoxybenzyl)oxy)propan-
1-ol (1.80 g,3.56 mmol) in DCM (18 mL) at O °C was added Et3SiH (5.68 mL,35.6 mmol)
followed by TFA (2.72 mL,35.6 mmol). The mixture was warmed slowly to room temperature
over 3 h. The resulting solution was quenched by careful addition of sat. aq. NaHCO3 (20 mL). The
phases were separated,and the aq. phase was ted with DCM (2 x 30 mL). The combined
organic phases were washed with brine (50 mL),dried over Na2SO4, filtered,and concentrated. The
resulting oil was purified by flash column tography (Si02, o?10% acetone in hexanes) to
afford the title compound (742 mg,56%) as a colorless oil: 1H NMR (300 MHz,CDCh)o 7.51-
7.36 (m,4H),7.25- 7.17 (m,2H),7.18- 7.06 (m,2H),4.48 (dq,J= 8.2,6.1 Hz,lH),3.76 (d,J=
1H),2.80(s,lH), 1.19(d,J=6.2Hz,3H);13CNMR(75MHz,CDCh)o ,139.85,
131.98,131.85,130.39,129.84,121.06,120.72,69.82,58.91,21.65; (Thin film) 3390, 3024, 2969,
2900,1486,1072 cm-1•
Example 3D, Step 1: Preparation of(S)-1,1-bis(4-((trimethylsilyl)ethynyl)-
phenyl)propanol.
1002106834
HO HO
To a solution of(S)-1,1-bis(4-bromophenyl)propanol (1.01 g,2.72 mmol) in
THF (9 mL) was added bis(triphenylphosphine)palladium dichloride (0.095 g,0.136 mmol) and
copper(!) iodide (Cul; 0.026 g,0.136 mmol). The mixture was sparged withN2 for 20 min, and
triethylamine (Et3N; 4.53 mL) was added dropwise. To the resulting mixture was added
ethynyltrimethylsilane (1.15 mL, 8.15 mmol) dropwise,and the mixture was heated to reflux and
d overnight. The mixture was cooled to room temperature, and the reaction was quenched with
sat. aq. NaHCO3 • The products were extracted with EtOAc (2x), and the combined organic layers
were washed with brine, dried over Na2SO4, ed and concentrated. The crude e was then
purified by flash column chromatography (SiO2, 0?20% acetone in hexanes) to provide the title
compound (495 mg,45%) as a brown foam: 1H NMR (400 MHz, CDCb) o 7.48-7.42 (m,2H),
7.42-7.37 (m, 2H), 7.33-7.27 (m, 2H), 7.24- 7.17 (m,2H), 4.51 = 12.2,6.1, 3.5 Hz, lH),
3.81 (d, J= 8.3 Hz, lH), 1.60 (d,J= 3.8 Hz,lH),1.18 (d,J= 6.1 Hz, 3H),0.26 (s,9H),0.26 (s,
9H);13C NMR (101 MHz, CDC'3) o 142.55,141.48,132.42, 132.29, 128.69, 128.15,121.90,
121.57, , 104.71, 94.33,69.76,59.96,21.55, 0.00; (Thin flm) 3397, 2960,2156,
1501,1248,861,840 cm-1; HRMS-ESI (m/z) [M+Ht calcd for C25H33OSb, 405.2064; found,
405.2070.
[0085] Example 3D, Step 2: Preparation of (S)-1,1-bis(4-ethynylphenyl)propanol.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
HO HO
....CH3
H3C... 'CH3
To a solution of(S)-1, 1-bis(4-((trimethylsilyl)ethynyl)phenyl)propanol (0.470
g, 1.16 mmol) in methanol (MeOH; 5.8 mL) was added potassium carbonate (K.2CO3; 0.482 g, 3.48
mmol). The mixture was stirred for 1 hat room temperature and then filtered through Celite®. The
filter cake was washed with MeOH, and the filtrate was concentrated. The crude material was
purified by flash column chromatography (SiO2, 0?20% acetone in hexanes) to provide the title
compound (288 mg, 95%) as a yellow oil: 1H NMR (300 MHz, CDCh) o 7.48- 7.43 (m, 2H), 7.43
- 7.39 (m, 2H), 7.35 - 7.29 (m, 2H), 7.24- 7.19 (m, 2H), 4.51 (dqd, J= 8.3, 6.1, 3.7 Hz, lH), 3.82
(d, J= 8.3 Hz, lH), 3.05 (s, IH), 3.04 (s, IH), 1.63 - 1.55 (m, IH), 1.18 (d, J= 6.1 Hz, 3H); 1 3C
NMR (101 MHz, CDCh) o 142.84, 141.82, 132.60, 132.48, 128.74, 128.22, 120.87, 120.57, 83.31,
83.29, 77.39, 77.29, 69.73, 59.96, 21.66; (Thin film) 3436, 3280, 2968, 2106, 1499, 1075, 825 cm-1;
HRMS-ESI (mlz) [M+Ht calcd for C19H17O, 261.1274; found, 261.1272.
Example 3D, Step 3: Preparation 1, 4-ethylphenyl)propanol.
?.::CH1/
HO HO
To a solution of (S)-1,1-bis(4-ethynylphenyl)propanol (0.144 g, 0.553 mmol)
in EtOAc (2.8 mL) was added palladium (5% weight (wt) on carbon, dry basis; 0.235 g, 0.055
mmol). The mixture was d under a balloon ofhydrogen overnight. The e was filtered
1002106834
through Celite®, and the filter cake was washed with EtOAc. The combined filtrate was then
concentrated, and the crude residue was purified by flash column tography (SiO2, 0?25%
acetone in hexanes) to provide the title compound (97.0 mg, 65%) as a clear oil: 1HNMR (400
MHz, CDC'3) 8 7.33-7.25(m, 2H), 7.22-7 .15 (m, 2H), .11 (m, 2H), 7.10 (d, J= 8.1 Hz,
2H), 4.51 (dqd, J= 8.7, 6.1, 2.5 Hz, lH), 3.74 (d, J= 8.9 Hz, IH), 2.65 -2.53 (m, 4H), 1.68 (d, J=
2.8 Hz, lH), 1.23-1.14 (m, 9H); 13C NMR (101 MHz, CDC'3) 8 142.74, 142.33, , 138.91,
128.48, 128.40, 128.07, 128.02, 70.19, 60.02, 28.41, 28.39, 21.37, 15.47, 15.46;(Thin film) 3421,
2963, 1510, 1110, 821 cm-1; HRMS-ESI (m/z) t) calcd for C19H24NaO, 291.1719; found,
291.1 725.
Example 3E: Preparation of l-(9H-xanthenyl)ethanol.
To a solution of 9H-xanthene(364 mg, 2.00 mmol) in THF (10 mL) at -78 °C
was added n-butyllithium (2.5 M in hexanes; 0.880 mL, 2.20 mmol). The mixture was stirred at -78
°C for 30 min. Acetaldehyde (0.226 mL, 4.00 mmol) was added, and the reaction mixture was
warmed slowly to room temperature ght. The resulting solution was quenched by careful
addition of sat. aq. NH4Cl (10 mL). The phases were separated, and the aq. phase was extracted
with Et2O (2 x 15 mL). The combined organic phases were washed with brine (20 mL), dried over
Na2SO4, filtered, and concentrated. The resulting oil was purified by flash column chromatography
(Si02, o?10% acetone in hexanes) to afford the title compound (216 mg, 48%) as a colorless oil:
1H NMR (400 MHz, CDC'3) 8 7.33-7.22 (m, 4H), 7.17-7.04 (m, 4H), 3.99 (d, J= 5. l Hz, lH),
3.96-3.82(m, lH), 1.54(d,J= 6.0 Hz, IH), l.00(d,J= 6.3Hz, 3H); 13CNMR(I01 MHz,
CDC'3)8152.94, 152.65, 129.54, 129.30, 128.19, 128.17, 123.18, 123.14, 122.48, 121.73, ,
116.41, 73.07, 47.06, 18.81; ESIMS (m/z) 475 ([2M+Nat).
Example 3F: ation of(1S,2S)-l -phenyl(4-
(trifluoromethyl)phenyl)propanol.
!002106834
To a mixture ofmagnesium turnings (102 mg, 4.20 mmol) in Et2O (4 mL) was
added 1-bromo(trifluoromethyl)benzene (0.588 mL, 4.20 mmol) at room ature, followed
by Mel (5 µL). Upon warming to a gentle boil using a heat gun, the mixture turned a yellow/brown
color. The reaction was then stirred in a water bath at room temperature for 30 min until almost all
the ium was consumed. This was added to a suspension ofcopper(!) iodide (Cul; 400 mg,
2.10 mmol) in Et2O ( 4 mL) at -78 °C. The reaction was stirred at -20 °C for 30 min, then cooled to -
78 °C, and (2S,3S)methylphenyloxirane (0.201 mL, 1.50 mmol) was added. The resulting
IO mixture was warmed slowly to room temperature overnight. The resulting solution was quenched
by l addition of sat. aq. NH4Cl (10 mL). The phases were separated, and the aq. phase was
extracted with Et2O (2 x 15 mL). The combined c phases were washed with brine (20 mL),
dried over Na2SO4, filtered, and concentrated. The resulting oil was purified by flash column
chromatography (Si02, O? I0% e in hexanes) to afford the title compound (390 mg, 94%) as
a light yellow oil: 1H NMR (400 MHz, CDCh) 8 7.60- 7.50 (m, 2H), 7.48- 7.38 (m, 2H), 7.38-
7.33 (m, 4H), 7.30- 7.23 (m, IH), 4.58 (dqd,J= 8.4, 6.1, 3.5 Hz, IH), 3.88 (d, J= 8.5 Hz, IH),
1.65 (d,J= 3.6 Hz, lH), 1.20 (d,J= 6.1 Hz, 3H); 19F NMR (376 MHz, CDCb) 8 -62.49; ESIMS
(mlz) 263 ([M-OH]l,
[0093) Example 3G, Step 1: Preparation of4,4'-(2-oxopropane-l,1-diyl)dibenzonitrile.
To a suspension of 4-bromobenzonitrile (546 mg, 3.00 mmol) and cesium
carbonate (977 mg, 3.00 mmol) in THF (10 mL) under anN2 atmosphere was added acetone (1.10
mL, 15.00 mmol), followed by X-Phos Pd 03 (50.8 mg, 0.060 mmol). Then, the vial was sealed
and heated to 55 °C for 4 days. The reaction was diluted with EtOAc (30 mL) and washed with sat.
1002106834
NH4Cl (3 x 10 mL), water (15 mL), and brine (15 mL). Then the organic phase was dried over
, filtered, and concentrated. The resulting oil was purified by flash column chromatography
(SiO2, 0?40% EtOAc in hexanes) to affordthe title compound (174 mg, 22%) as a colorless oil:
1HNMR (400 MHz, CDCh) 8 7.66 (d, J= 8.4 Hz, 4H), 7.34 (d, J= 8.3 Hz, 4H), 5.21 (s, IH), 2.29
(s, 3H); 13C NMR (101 MHz, CDCb) 8 203.68, 142.15, 132.75, 129.64, 118.21, , 64.25,
.43; ESIMS m/z 261 ([M+Ht).
Example 3G, Step 2: Preparation of (S)-4,4'-(2-hydroxypropane-1,1-
diyl)dibenzonitrile.
CN CN
CN CN
To a solution of 4,4'-(2-oxopropane-l,1-diyl)dibenzonitrile (174 mg, 0.668
mmol) in e (4.5 mL) was added (R)methyl-3,3-diphenylhexahydropyrrolo[l,2-
c][l,3,2]oxazaborole (1 M solution in toluene, 66.8 µL, 0.067 mmol). Then, the on was
cooled to O °C and a solution of BH3-DMS (69.8 µl, 0.735 mmol) in 0.5 mL toluene was added
over 2 min. The flask was left to stir at O °C. After 2 h, the reaction was quenched with methanol
(0.5 mL), diluted with EtOAc and added water. Phases were separated and the aqueous phase
was extracted with EtOAc x 2. The combined organic phases were washed with brine (20 mL),
dried overNa2SO4, filtered, and trated. The resulting oil was purified by flash column
chromatography (Si02, 0?50% EtOAc in hexanes) to afford the title compound (99.7 mg, 57%)
as a colorless oil: 1HNMR (400 MHz, CDCh) 8 d 7.60 (dd,J = 8.4, 6.8 Hz, 4H), 7.51-7.46 (m,
2H), 7.43 -7.37 (m, 2H), 4.63-4.47 (m, lH), 3.97 (d, J= 7.5 Hz, lH), 1.97 (d, J = 3.8 Hz, lH),
1.21 (d, J= 6.2 Hz, 3H). 13C NMR (101 MHz, CDCh) 8 146.91, 145.86, 132.60, 132.45, 129.90,
129.19, , 118.51, 110.96, 110.92, 69.19, 59.56, 22.27; ESIMS m/z 263 ([M+Ht).
[0097] Example 3H, Step 1: Preparation of 3,3-diphenylbutanone.
1002106834
To a magnetically stirred mixture of 2,3-diphenylbutane-2,3-diol (500 mg, 2.06
mmol) in DCM (10 mL) was added antimony hloride (26.5 µL, 0.206 mmol) under air
atmosphere. The on mixture was stirred at 25 °C for 1 h and then was quenched by slow
addition of sat. aq. NaHCO3• The ing mixture was diluted with water and additional DCM,
and the organic layer was ted by passing through a phase separator. The resulting oil was
purified by flash column chromatography (SiO2, 0?5% acetone in hexanes) to afford the title
compound (330 mg, 71%) as a ess oil: 1HNMR (400 MHz, CDCb) 8 7.36-7.31 (m, 4H),
7.30- 7.25 (m, 2H), .15 (m, 4H), 2.11 (s, 3H), 1.87 (s, 3H); 13C NMR (101 MHz, CDCh) 8
209.16, 143.59, 128.36, 126.91, 62.32, 27.62, 26.42; ESIMS m/z 225 ([M+H]l.
Example 3H, Step 2: Preparation of (S)-3,3-diphenylbutanol.
To a solution of 3,3-diphenylbutanone (150 mg, 0.669 mmol) in toluene (4.5
mL) was added (R)-l-methyl-3,3-diphenylhexahydropyrrolo[l,2-c][l,3,2]0xazaborole (1 M
solution in toluene, 134 µL, 0.134 mmol). Then, a solution ofBH3-DMS (70.2 µL, 0.702 mmol) in
0.5 mL oftoluene was added to the reaction mixture over 2 min. The flask was left to stir at room
temperature. After 1 h, the reaction was quenched with ol (0.5 mL). DCM and water were
added, and the phases were separated. The aqueous phase was ted with DCM (2x). The
combined organic phases were washed with brine (20 mL), dried over Na2SO4, filtered, and
concentrated. The resulting oil was purified by flash column chromatography (SiO2, 0?20%
acetone in hexanes) to afford the title compound (150 mg, 99%) as a colorless oil: 1HNMR (400
MHz, CDCl3) 8 d 7.39 - 7.17 (m, lOH), 4.70-4.61 (m, lH), 1.67 (s, 3H), 1.51 (d,J= 4.9 Hz, lH),
1.11 (d, J= 6.3 Hz, 3H); 13C NMR (101 MHz, CDCh) 8 147.30, 145.86, 128.40, 128.15, 128.05,
127.79, 126.20, 126.01, 72.28, 51.77, 23.26, 18.39; ESIMS mlz 227 ([M+Ht).
Example 31, Step 1: Preparation of(S)-l,l-bis(2,3-dimethoxyphenyl)propane-
1,2-diol.
,...,..o
To a solution ofisopropylmagnesium lithium chloride (1.3 Min THF, 6.1 mL,
8.00 mmol) was added THF (2 mL) and l-bromo-2,3-dimethoxybenzene (1.74 g, 8.00 mmol). The
resulting brown solution was heated to a gentle reflux (75 °C external temp) for 2.5 h, then cooled
to O °C in an ice water bath. (S)-methyl 2-hydroxypropanoate (0.191 ml, 2 mmol) was then added
dropwise via syringe. The reaction was stirred at O °C for 1 h, then removed from the cold bath and
stirred overnight at rt. The reaction was cooled to O °C in an ice water bath, diluted with water (20
mL), brine (20 mL), and Et20 (40 mL), and was quenched with 1 N HCI (8 mL). The phases were
separated, and the aqueous phase was ted with EhO (20 mL). The c phases were
ed, dried over MgS04, filtered, and concentrated to provide an oil. Purification by
automated silica gel column chromatography (5-50% EtOAc in hexanes) provided the title
compound (568 mg, 82%) as a yellow, crystalline solid: 1H NMR (300 MHz, CDCb) 8 7.43 (td, J=
8.0, 1.5 Hz, 2H), 7.11 (td, J= 8.1, 4.9 Hz, 2H), 6.83 (dd, J= 8.1, 1.4 Hz, 2H), 5.06 -4.82 (m, lH),
4.74 (d, J= 1.2 Hz, lH), 3.81 (s, 3H), 3.80 (s, 3H), 3.20 (s, 3H), 3.04 (s, 3H), 2.86 (d, J= 9.5 Hz,
lH), 0.97 (d, J= 6.4 Hz, 3H); 13C NMR (126 MHz, CDCb) 8 152.89, 152.82, 146.94, 145.53,
139.56, 138.92, 123.32, 123.26, 122.01, , 111.30, 79.20, 77.22, 60.07, 59.26, 55.77, 55.64,
18.34; HRMS-ESI (mlz) ([M+Nat) calcd for C19H2406Na, 371.1465; found, 371.1456.
Example 31, Step 2: Preparation of 1, 2,3-dimethoxyphenyl)propanone.
HO - 0
.,.....o .,.....o
0 0
I I
1002106834
To a solution of (S)-1,1-bis(2,3-dimethoxyphenyl)propane-l ,2 -diol (560 mg,
1.61 mmol) in anhydrous CH2Ch (8 mL) at O °C was added triethylsilane (770 µl,4.82 mmol) and
trifluoroacetic acid (TFA, 124 µL,1.61 mmol). The resulting solution was stirred at O °C for 2 h,
then removed from the cold bath and stirred for 2 h. TFA (248 µL,3.2 mmol) was added,and the
reaction was then stirred overnight at rt. The reaction was d with water (25 mL) and extracted
with CH2Ch (3x 25 mL). The organic extracts were dried over Na2S04,filtered,and concentrated
to provide an oil. Purification by automated silica gel column chromatography (5-25% acetone in
hexanes) provided the title compound (396 mg,75%) as a white solid: 1H NMR (300 MHz,CDC13)
8 6.99 (t,J= 8.0 Hz,2H),6.87 (dd,J= 5 Hz,2H),6.67 -6.54 (m,2H),5.86 (s,lH),3.87 (s,
6H),3.75 ,2.25 (s,3H); 13C NMR (126 Ch) 8 207.18,152.69, 147.02, 132.23,
,121.61,111.64,60.36,55.74, 51.96, 29.80; HRMS-ESI(m/z) ([M+Na]l calcd for
C19H2205Na,353.1359; found,353.1353.
Example 31, Step 3: Preparation of l,l-bis(2,3-dimethoxyphenyl)propanol.
0 - HO
,,,,.o ,,,,.o
I 0
] To a solution of 1,1-bis(2,3-dimethoxyphenyl)propanone (356 mg,1.08
mmol) in methanol (3.5 mL) was added sodium borohydride (61 mg,1.6 mmol). The ing
solution was stirred at rt for 20 h,then was quenched with sat'd NHiCl (1 mL),diluted with water
(20 mL) and extracted with CH2Ch (3x 20 mL). The organic extracts were combined,dried over
Na2S04,filtered,and concentrated to provide the title compound (360 mg,100%) as an oil: 1H
NMR(300 MHz,CDCb) 8 7.16-6.88 (m,4H),6.79 (ddd,J= 9.6,7.8,1.9 Hz,2H),4.81 (d,J=
8.3 Hz,lH),4.53-4.32 (m,lH),3.84 (s,3H),3.84 (s,3H),3.77 (s,3H),3.76 (s,3H),2.04 (d,J=
4.2 Hz,lH),1.22 (d,J= 6.2 Hz,3H); 13C NMR (126 Ch) 8 152.98,152.83,147.71,
147.04,136.17,135.33,123.94,123.62,120.96,120.84,110.76,110.48,70.32,60.26,60.20,55.66,
55.63,45.11,21.80; tfilm) 3451,2935,2833,1582,1473,1428,1266, 1215, 1167,1125,
1088, 1068,1004,964,908,835,809,787,748,728.
1002106834
Example 4A: Preparation (S)-1,1-diphenylpropanyl 2-((tert-
butoxycarbonyl)amino)-propanoate.
BocHN,,,,.(o
BocHN HO
,,,,rOH + CH3
[00108] To a on of (S)-1,1-diphenylpropanol (317 mg, 1.493 mmol) in DCM
(15 mL) at O °C were added (S)((tert-butoxycarbonyl)amino)propanoic acid (Boe-Ala-OH; 311
mg, 1.64 mmol) andN,N-dimethylpyridinamine (DMAP; 18.2 mg, 0.149 mmol) followedbyN1-
((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (EDC; 573 mg, 2.99
mmol), and the reaction e was stirred at room temperature overnight and concentrated to give
a yellow oil. The crude material was purified by flash column chromatography (Si02, 1?10%
acetone in hexanes) to afford the title compound (433 mg, 75%) as a colorless oil: 1H NMR (400
MHz, CDCb)87.42-7.07 (m, l0H), 5.80 (dq, J= 10.1, 6.1 Hz, lH), 4.97 (d,J= 8.0 Hz, lH), 4.19
-4.06 (m, 1H), 4.03(d,J= 10.1 Hz, lH), 1.41 (s,9H), 1.23 (d,J=6.l Hz, 3H), 0.76(d,J=7.2Hz,
3H); 13CNMR(101MHz,CDCb)8172.83, 154.96, , 141.26, 128.79, 128.50, 128.10,
128.08, 126.91, 126.67, 79.62, 73.10, 57.98, 49.21, 28.33, 19.31, 17.98; ESIMS m/z 384 ([M+H]l.
Example 5, Step 1: Preparation of(S)(((S)-l,l-diphenylpropanyl)oxy)-l-
oxopropanaminium chloride.
BocHN,,,,.fO
[00110] To a solution of (S)-(S)-1,l-diphenylpropanyl 2-((tertbutoxycarbonyl
)amino)propanoate (Cmpd 2; 433 mg, 1.13 mmol) in DCM (6 mL) was added a 4 N
solution ofHCI in dioxane (2.8 mL, 11.3 mmol), and the mixture was stirred for 3 h at room
temperature. The solvent was evaporated under a stream ofN2 to provide the title compound (360
mg, 100%) as a white solid: ESIMS (mlz) 284 ([M+Ht).
1002106834
Example 5, Step 2: Preparation of(S)-(S)-1,1-diphenylpropanyl 2-(3-
hydroxymethoxypicolinamido)propanoate.
Cl H3N,,,'(Jl,
0 -
[00112] To a solution of (S)(((S)-l,1-diphenylpropanyl)oxy)oxopropan
m de (Cmpd 46; 361 mg, 1.13 mmol) and oxymethoxypicolinic acid (210
mg, 1.24 mmol) in DCM (11 mL) were added benzotriazolyl-oxytripyrrolidinophosphonium
hexafluorophosphate (PyBOP; 646 mg, 1.24 mmol) and N-ethyl-N-isopropylpropanamine
(DIPEA; 0.651 mL, 3.72 mmol), and the reaction mixture was stirred for 2 hat room temperature.
The solvent was evaporated and the crude oil was purified by flash column chromatography (Si02,
1?50% acetone in hexanes) to afford the title compound (340 mg, 70%) as a white foam: 1H NMR
(400 MHz, CDCb) 8 12.10 (s, lH), 8.34 (d, J= 8.0 Hz, lH), 7.98 (d, J= 5.2 Hz, lH), 7.38-7.06
(m, l0H), 6.86 (d, J= 5.3, lH), 5.83 (dq, J= 10.1, 6.1 Hz, lH), 4.52 (dq, J= 8.1, 7.2 Hz, lH), 4.06
(d, J= 10.2 Hz, lH), 3.93 (s, 3H), 1.26 (d, J= 6.1 Hz, 3H), 0.97 (d, J= 7.2 Hz, 3H); 3C NMR (101
MHz, CDCb) 8 171.67, 168.53, 155.34, 148.72, 141.38, 141.13, 140.40, 130.48, 128.80, 128.50,
128.10, , 126.95, 126.70, 109.39, 73.57, 57.93, 56.07, 47.85, 19.24, 17.61; HRMS-ESI (m/z)
([M+Ht) calcd for C25H27N205, 435.1920; found, 435.1925.
Example 6A: ation of(S)-(S)-1,1-diphenylpropanyl 2-(3-acetoxy
ypicolinamido)propanoate.
To a solution of (S)-(S)-1,l-diphenylpropanyl 2-(3-hydroxy
methoxypicolinamido)-propanoate (Cmpd 90; 70.0 mg, 0.161 mmol), Et3N (44.9 µL, 0.332 mmol),
1002106834
and DMAP(3.94 mg, 0.032 mmol) in DCM (3.2 mL) was added acetyl chloride (17.2 µL,0.242
mmol) at room temperature,and the reaction mixture was stirred for 2 h. The solvent was
evaporated,andthe resulting crude oil was ed by flash column chromatography (Si02,
1?40% acetone in hexanes) to afford the title compound (75.0 mg,97%) as a colorless oil: 1H
NMR(4OOMHz,CDC'3)o8.41 (d,J= 7.8 Hz,IH),8.3O(d,J= 5.4Hz,lH), 7.38-7.lO(m,lOH),
6.97 (d,J= 5.4 Hz, lH),5.82 (dq,J= 10.0,6.2 Hz,1H),4.52 (dt,J= 8.2,7.1 Hz,lH), 4.05(d,J=
.1 ,3.87 (s, 3H),2.37(s,3H),1.24 (d,J= 6.1 Hz, 3H),0.89(d,J= 7.1 Hz,3H); 13C
NMR (101 C'3) o 172.23,168.89,162.28, 159.42,146.66,141.55,141.44,141.25,
137.45, 128.77,128.50,128.13,128.11,126.89,126.67,109.73,73.32,57.90,56.27,47.85,20.75,
19.25,17.92; SI (mlz) ([M+Ht) calcd for C27H29N206,477.2025; found,477.2019.
Example 6B: Preparation of(S)-(S)-1,1-diphenylpropanyl 2-(3-
(acetoxymethoxy)methoxypicolinamido)propanoate.
To a suspension of (S)-(S)-1,l-diphenylpropanyl 2-(3-hydroxy
methoxypicolinamido)-propanoate (Cmpd 90; 100 mg,0.230 mmol) and K2C03 (63.6 mg,0.460
mmol) in acetone (4.6 mL) was added bromomethyl acetate (33.9 µL,0.345 mmol) at room
temperature,and the mixture was heated to 55 °C for 3 h and then cooled to room temperature. The
solvent was evaporated and the resulting crude material was ed by flash column
chromatography(Si02,1?40% acetone in hexanes) to afford the title compound(94.0 mg,80%
yield) as a colorless oil: 1H 0 MHz,CDC'3) o 8.25 (d,J= 5.4 Hz,lH), 8.22 (d,J= 7.9 Hz,
lH), 7.34-7.09 (m, !OH),6.92 (d, J= 5.4 Hz,lH),5.83 (dq, J= .2 Hz,lH),5.72 (d,J= 0.7
Hz,2H),4.60 -4.49 (m,lH),4.06(d,J= 10.1 Hz,lH), 3.88(s,3H),2.05(s,3H),1.25 (d, J= 6.1
Hz,3H),0.91(d,1= 7.2 Hz,3H); (101 MHz,CDC'3) o 172.33,170.25,162.88,160.24,
145.70,143.91, 142.54,141.48,141.25,128.76,128.49,128.12,128.09,126.89,126.65, 109.56,
1002106834
89.50, 73.27, 57.92, 56.17, 48.07, 20.86, 19.25, 17.73; HRMS-ESI (m/z) [M+Ht calcd for
C2sH31N207, 507.2131; found, 507.2125.
Example 6C: Preparation of(S)-(S)-1,1-diphenylpropanyl 2-(3-
( (isobutyryloxy)methoxy)methoxypicoIinamido)propanoate.
To a solution of (S)-(S)-1,1-diphenylpropanyl 2-(3-hydroxy
methoxypicolinamido)-propanoate (Cmpd 90; 100 mg, 0.230 mmol) in acetone (4.6 mL) were
added sodium carbonate (Na2C03; 73.2 mg, 0.690 mmol), sodium iodide (Nal; 6.90 mg, 0.046
mmol) and chloromethyl 2-ethoxyacetate (62.9 mg, 0.460 mmol). The mixture was heated to 55 °C
overnight and then cooled to room temperature, and the solvent was evaporated. The resulting
residue was ed by flash column chromatography (S i02, 2?30% acetone in hexanes) to afford
the title compound (79.0 mg, 64%) as a colorless oil: 1H NMR (400 MHz, CDCh) o 8.28 (d, J= 7.9
Hz, IH), 8.25 (d, J= 5.3 Hz, lH), 7.36-7.08 (m, lOH), 6.92 (d, J= 5.4 Hz, IH), 5.83 (dq, J= 10.1,
6.2 Hz, lH), 5.79-5.69 (m, 2H), 4.62-4.44 (m, lH), 4.06 (d, J= 10.1 Hz, lH), 3.86 (s, 3H), 2.53
(hept, J= 7.0 Hz, lH), 1.25 (d, J= 6.2 Hz, 3H), 1.13 (d, J= 7.0 Hz, 6H), 0.91 (d, J= 7.2 Hz, 3H);
1 3CNMR(lO1 MHz, CDC'
3) 8176.22, , 162.85, 160.23, 145.55, 144.16, 142.18, 141.48,
141.26, 128.76, 128.49, 128.12, 128.09, , 126.65, 109.48, 89.90, 73.26, 57.93, 56.12, 48.07,
33.85, 19.26, 18.68, 17.74; HRMS-ESI (m/z) ([M+H]l calcd for C30H35N207, 535.2444; found,
Example A: tion ofFungicidal ty: LeafBlotch of Wheat
(Zymoseptoria i; Bayer code SEPTTR):
[00120] Technical grades of materials were dissolved in acetone, which were then mixed
with nine volumes ofwater (H20) containing 110 ppm Triton X-1OO. The fungicide solutions were
1002106834
applied onto wheat seedlings using an automated booth sprayer to f. All sprayed plants were
allowed to air dry prior to further handling. All fungicides were evaluated using the aforementioned
method for theiractivity vs. all target diseases, unless stated otherwise. Wheat leaf blotch and
brown rust activity were also evaluated using track spray applications, in which case the fungicides
were formulated as EC formulations, containing 0.1% Trycol 5941 in the spray solutions.
Wheat plants (variety Yuma) were grown from seed in a ouse in 50%
mineral 0% soil-less Metro mix until the first leaf was fully emerged, with 7-10 seedlings per
pot. These plants were inoculated with an aqueous spore suspension of Zymoseptoria tritici either
prior to or after fungicide treatments. After inoculation the plants were kept in 100% relative
humidity (one day in a dark dew chamber followed by two to three days in a lighted dew chamber
at 20 °C) to permit spores to ate and infect the leaf. The plants were then transferred to a
greenhouse set at 20 °C for disease to develop. When disease symptoms were fully expressed on the
1st leaves of untreated plants, infection levels were assessed on a scale of0 to 100 percent disease
severity. Percent disease control was calculated using the ratio of disease ty on treated plants
relative to untreated plants.
] Example B: Evaluation of Fungicidal Activity: Wheat Brown Rust (Puccinia
triticina;Synonym: Puccinia recondita f. sp. tritici; Bayer code PUCCRT):
Wheat plants (variety Yuma) were grown from seed in a greenhouse in 50%
mineral soil/50% soil-less Metro mix until the first leaf was fully emerged, with 7-10 seedlings per
pot. These plants were inoculated with an aqueous spore sion of Puccinia triticina either
prior to or after fungicide ents. After inoculation the plants were kept in a dark dew room at
22 °C with 100% relative humidity overnight to permit spores to germinate and infect the leaf. The
plants were then transferred to a ouse set at 24 °C for e, to develop. Fungicide
formulation, application and e ment followed the procedures as described in the
Example A.
Example C: Evaluation of Fungicidal Activity: Wheat Glume Blotch
(Leptosphaeria nodorum;Bayer code ):
[00125] Wheat plants (variety Yuma) were grown from seed in a greenhouse in 50%
mineral soil/50% soil-less Metro mix until the first leaf was fully emerged, with 7-10 seedlings per
pot. These plants were inoculated with an aqueous spore suspension of Leptosphaeria nodorum 24
1002106834
h after ide treatments. After inoculation the plants were kept in 100% ve humidity (one
day in a dark dew chamber followed by two days in a lighted dew chamber at 20 °C) to permit
spores to ate and infect the leaf. The plants were then transferred to a greenhouse set at 20 °C
for disease to develop. Fungicide formulation, application and disease ment followed the
procedures as described in the Example A.
[00126) Example D: Evaluation ofFungicidal ty: Apple Scab (Venturia
inaequalis; Bayer code VENTIN):
[00127) Apple seedlings (variety McIntosh) were grown in soil-less Metro mix, with one
plant per pot. Seedlings with two expanding young leaves at the top (older leaves at bottom ofthe
plants were trimmed) were used in the test. Plants were inoculated with a spore suspension of
Venturia inaequalis 24 h after fungicide treatment and kept in a 22 °C dew r with I00%
ve ty for 48 h, and then moved to a greenhouse set at 20 °C for disease to develop.
Fungicide formulation, application and disease assessment on the sprayed leaves followed the
procedures as described in the Example A.
[00128) Example E: Evaluation ofFungicidal Activity: LeafSpot ofSugar Beets
(Cercospora betico!a; Bayer code CERCBE):
[00129) Sugar beet plants (variety HH88) were grown in soil-less Metro mix and
trimmed regularly to in a uniform plant size prior to test. Plants were inoculated with a spore
suspension 24 h after fungicide treatments. Inoculated plants were kept in a dew chamber at 22 °C
for 48 h then incubated in a greenhouse set at 24 °C under a clear plastic hood with bottom
ation until disease symptoms were fully expressed. Fungicide formulation, application and
disease assessment on the sprayed leaves followed the procedures as described in the Example A.
[00130) Example F: Evaluation of Fungicidal Activity: Asian n Rust
(Phakopsorapachyrhizi; Bayer code PHAKPA):
[00131) Technical grades ofmaterials were ved in acetone, which were then mixed
with nine volumes ofH2O containing 0.011 % Tween 20. The fungicide solutions were applied onto
soybean seedlings using an automated booth sprayer to run-off. All sprayed plants were allowed to
air dry prior to further handling.
1002106834
[00132) n plants ty ms 82) were grown in soil-less Metro mix, with
one plant per pot. Two weeks old seedlings were used for testing. Plants were inoculated either 3
days prior to or 1 day after fungicide treatments. Plants were incubated for 24 h in a dark dew room
at 22°C and 100% relative humidity then transferred to a growth room at 23 °C for e to
develop. Disease severity was assessed on the sprayed leaves.
[00133) Example G: Evaluation ofFungicidal Activity: Barley Scald (Rhyncosporium
s; Bayer code RHYNSE):
[00134) Barley seedlings (variety Harrington) were propagated in soil-less Metro mix,
with each pot having 8 to 12 plants, and used in the test when the fir?t leaf was fully emerged. Test
plants were inoculated by an aqueous spore suspension ofRhyncosporium secalis 24 h after
fungicide treatments. After inoculation the plants were kept in a dew room at 22°C with 100%
relative humidity for 48 h. The plants were then transferred to a greenhouse set at 20 °C for disease
to develop. Fungicide formulation, application and e assessment on the sprayed leaves
followed the procedures as described in the Example A.
[00135) Example H: Evaluation ofFungicidal Activity: Rice Blast (Pyricularia oryzae;
Bayer code ):
[00136) Rice seedlings (variety Japonica) were propagated in soil-less Metro mix, with
each pot having 8 to 14 , and used in the test when 12 to 14 days old. Test plants were
inoculated with an aqueous spore suspension ofPyricularia o,yzae 24 h after fungicide treatments.
After inoculation the plants were kept in a dew room at 22°C with 100% relative humidity for 48 h
to permit spores to germinate and infect the leaf. The plants were then transferred to a greenhouse
set at 24 °C for disease to develop. Fungicide formulation, application and disease assessment on
the sprayed leaves followed the procedures as described in the Example A.
[00137) Example I: Evaluation ofFungicidal Activity: Tomato Early Blight (Alternaria
solani; Bayer code AL TESO):
) Tomato plants (variety Outdoor Girl) were ated in ess Metro mix,
with each pot having one plant, and used when 12 to 14 days old. Test plants were inoculated with
an aqueous spore suspension ofAlternaria solani 24 h after ide treatments. After inoculation
the plants were kept in a dew room at 22 °C with I00% relative humidity for 48 h to permit spores
1002106834
to germinate and infect the leaf. The plants were then transferred to a growth room at 22 cc for
disease to develop. Fungicide formulation, application and disease assessment on the sprayed leaves
followed the procedures as described in the Example A.
[00139] e J: Evaluation ofFungicidal Activity: Cucumber cnose
(Colletotrichum lagenarium; Bayer code COLLLA):
Cucumber seedlings (variety Bush Pickle) were propagated in soil-less Metro
mix, with each pot having one plant, and used in the test when 12 to 14 days old. Test plants were
inoculated with an aqueous spore suspension ofColletotrichum lagenarium 24 hr after fungicide
treatments. After inoculation the plants were kept in a dew room at 22 cc with 100% relative
ty for 48 hr to permit spores to germinate and infect the leaf. The plants were then
transferred to a growth room set at 22 cc for disease to develop. Fungicide formulation, application
and disease assessment on the sprayed leaves followed the procedures as bed in the Example
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Table 1. Compound Structure, Preparation Method, and Appearance
Prepared
*Crnpd. According
Structure Appearance
No. To
H3C O ?'' f ,,, Example l;
0 Example
H 3C::Y Y \:Vhitc Solid
CH 3 0 CH 3 3A:
Example 4A
0 Example l;
H3C O ?'' f ,,, Example
0 2A:
2 H 3C::Y Y Colorless Oil
CH 3 0 CH 3 Example
0 e l;
H3C O ?" ,,, Example
,., f 0 2A:
_, H 3C::Y Y Colorless Oil
CH 3 0 CH 3 E:--;ample
Example 4A
H,C Example l;
OY?'' f ,,, 0 Example
H 3C::Y 2A: Clear,
4 CH 3 0 CH 3 Example Colorless Oil
E:--;arnple 4A
0 E:--;ample I:
H3C O ?" ,,, f Example
0 2B;
H 3C::Y Y Colorless Oil
CH 3 0 CH 3 Example
Example 4A
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
0 Example l;
::?:Y o Y?'"·?
Example
o 28:
6 Colorless Oil
CH3 0 CH3 Example
Example I:
O Y?'"·? 0
: :?:Y Example
7 CH3 0 CH3 F Colorless Oil
Example
Example 4A
0 Example l;
H3C O '' ?,,. Example
0 2C:
8 H3C:Y Y ess Oil
CH3 0 CH3 Example
0 'CH3
Example I;
::?>(o!(?" ?o Example
CH3 0 CH3 2A:
9 Colorless Oil
Example
Example 4A
0 Example l;
? Example
H3C O '' ?,,. 2A;
0 Colorless Oil
H3C:Y Y Example
CH3 0 CH3 3A;
Example 4A
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd. According
Structure Appearance
No. To
Example
0 Example 1:
Example
C O
11 ,,, 0 2A;
Colorless Oil
H3C H3 Y Y ?''f e
CH3 0 CH3
Example 4A
C O ,,, 0 Example
12 H3CH3 Y Y?''f 3E: Colorless Oil
CH3 0 CH3 Example 4A
Example
13 ::?Y0Y?,,.. fO 3E: Colorless Oil
CH3 0 CH3 Example 4A
::?Y0Y?'"·fO Example I:
14 Example
CH3 0 CH3 Colorless Oil
Example 4A
C O Example I;
,,, 0
Example
H3C H3 Y Y?''f ess Oil
CH3 0 CH3 3C;
Example 4A
[Annotation] an
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
::?Y 0 Example 1:
0 Example
CH3 Y?",r
16 0 CH3 Colorless Oil
Example
Example 4A
0 CH3 ?:
::?Y0Y?'",ro _,,, Example
18 3F: Colorless Oil
Example 4A
CH3 0 CH3
H3CYOY?" r,,. Example I:
0 Example
H3C 2A;
19 CH3 0 CH3 Colorless Oil
Example
Example 4A
:3?y o Example
3 y?Jl0 2A;
CH3 0 Clear Oil
Example
Example 4A
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
Example 1:
:3?:yoy?:(o Example
3 2A:
21 CH3 0 Clear Oil
H3C Example
Example 4A
H3C Example l;
O ?:c,,.
0 e
HC3 :Y Y 2A:
22 CH3 0 Clear Oil
H3C CH3 Example
Example 4A
Example l;
::?)( 1(?""·¢0 Example
~-)..,) CH3 0 CH3 Clear Oil
1/" I Example
CH3 Example 4A
Example I:
Example
24 Sticky Wax
Example 4A
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Prepared
*Cmpd. According
Structure Appearance
No. To
0 Example l;
H3C O ?'' f,,, Example
0 Sticky Wax
H3C)( r(
CH3 0 CH3 Example 4A
..,..CH3
H3C O '' f,,,
? 0 Example l;
H3C)( r( Example
26 CH3 0 CH3 Sticky Wax
Example 4A
o Example l;
? o
27 ?:?Y r( " ..f Example
Stich Wax
CH3 0 CH3 3C:
Example 4A
Example l;
Example
28 Example White Foam
3D, Steps
11 Example 4A
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. ing
Structure Appearance
No. To
0 CH3
::?)(o ?,, ?o Example 1:
r( Example
CH3 0 CH3 3C;
29 Example Sticky Wax
. Steps
Example 4A
0 CH3
::?)( o _..,,
?".. ?o Example
31 r( Clear Oil
CH3 0 CH3 3F:
Example 4A
HsC O ?'',,, (
0 Cl Example l;
H3C)( r(
...,..., Example
;):) CH3 0 CH3 White Solid
Example 4A
::?)( o ?'.. (o F Example I:
34 CH3 0 CH3 Example White Solid
Example 4A
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
Example 1:
::?)(ol(?""fo CH3 Example
,., - 2A;
.) ) CH3 0 CH3 White Solid
Example
CH3 Example 4A
H,C O t f,,. e l;
0 Example
36 H3C)( y \Vhite Foam
CH3 0 CH3 F 38:
Example 4A
0 Example I:
::?)( o Example
f 2A: Clear,
CH3 0 CH3 Example Colorless Oil
Example 4A
0 Example I:
HsC O ?'' f,,. Example
0 2A: Clear,
38 H3C)( I(
CH3 0 CH3 Example Colorless Oil
Example 4A
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
Example I:
Example
2A: Clear,
Example Colorless Oil
Example 4A
Example l;
Example
40 White Foam
Example
Example 4A
H3c ?'' f,,, e l;
)( r( 0 Cl e
H3C 2A;
43 CH3 0 CH3 White Solid
Example
Cl Example 4A
? '•-f Example l;
::?)( o
r( o F Example
44 CH3 0 CH3 White Solid
Example
F Example 4A
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example 5,
45 White Solid
Step 1
Example 5,
46 Colorless
Step 1 Oil
N ,,,,_
47 ? O Example 5,
Colorless Oil
Step 1
N "'•·
Example 5, Pale Yello\\
48 CH3
Step 1 Oil
Example 5,
49 Colorless Oil
Step I
Example 5,
50 Colorless
Step 1 Oil
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
E:xa111plc
H2N ,, f,,.
51 CH3 F Colorless Oil
Step 1
Example 5.
Colorless Oil
Step I
,. Jl
CH3 Example 5,
53 Colorless Oil
Step 1
,...0
H2N ,, f,,. E:xa111plc 5.
54 0 Colorless Oil
Step 1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. ing
Structure Appearance
No. To
Example
H2N ,, f,,, 0 Example 5,
55 Colorless Oil
Step 1
H2N ,, f,,, 0 Example 5.
(i Colorless Oil
CH3 Step I
Example 5.
57 Colorless Oil
Step I
58 Example 5,
ess Oil
Step 1
Example 5,
59 Colorless Oil
Step 1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure ance
No. To
Example
,. Jl
60 Example 5,
CH3 Colorless Oil
Step 1
Example 5.
61 White Solid
Step I
H2N,, Jl Example 5.
63 Colorless Oil
'O Step 1
'•·rCH3
Example 5,
64 Colorless Oil
Step 1
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
Example 5,
65 Sticky Oil
Step 1
Example 5,
66 Sticky Oil
Step 1
H2N ,, f,,.
0 e 5,
67 Sticky Oil
CH3 Step 1
H2N ,, f,,,
68 Example 5,
Sticky Wax
CH3 Step 1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
69 Sticky Wax
Step I
Example 5.
70 Sticky Wa:x
Step I
Example 5,
71 White Solid
Step I
Example 5,
72 White Solid
Step 1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure ance
No. To
Example
Example 5,
73 White Solid
Step 1
o F
H2N ,,,,.?
Example 5,
H3C White Solid
y Step 1
Example 5,
75 White Solid
Step 1
Example 5,
77 White Solid
Step l
Example 5,
78 White Solid
Step 1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
ure Appearance
No. To
Example
H2N ,, r,,,
0 Me
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H2N ,, f,,,
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0 Cl
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89 White Solid
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90 White Foam
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91 Colorless Oil
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?'"·?
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92 o \Vhitc Foam
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93 \Vhitc Foam
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Example 5,
95 Colorless Oil
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96 White Foam
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97 ?""? Example 5,
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102 Colorless Oil
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103 Colorless Oil
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104 Colorless Oil
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107 Colorless Gel
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110 Example 5, Clear,
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OH F
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116 White Solid
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118 \:Vhite Foam
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119 White Foam
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Example
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Example
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125 White Solid
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127 l
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135 0 Example 5,
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Colorless
138 Example 6B
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13lJ Example 6A ess Oil
140 Example 6A White Foam
141 Example 6B White Foam
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l.:J-2 Example 6C White Foam
143 Example 6A Colorless Oil
14.:J. Example 6B Colorless Oil
145 Example 6A Colorless Oil
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l.:J-6 Example 6B Colorless Oil
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l.:J-8 Example 6B Colorless Oil
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149 Example 6B Colorless Oil
1.50 Example 6A Colorless Oil
1.52 Example 6A Colorless Oil
153 Example 6B Colorless Oil
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155 Example 6A Colorless Oil
15h Example hA Colorless Oil
157 Example 6A Colorless Oil
158 Example 6B Colorless Oil
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Example 6B ess Oil
160 Example 6B Colorless Oil
161 Example 6A Colorless Oil
162 Example 6A Colorless Oil
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163 Example 6B Colorless Oil
16-J. e 6B Colorless Oil
165 Example 6A Colorless Oil
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166 Example 6A ess Oil
167 Example 6A Colorless Oil
168 Example 6A Colorless Oil
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160 Example 6B Colorless Oil
170 Example 6B Colorless Oil
171 Example 6B Colorless Oil
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173 Example 6A Colorless Oil
174 Example 6A Colorless Oil
17:'i Example 6B Colorless Oil
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176 Example 6B Colorless Oil
Clear.
178 Example 6B
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170 Example 6B
Colorless Oil
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181 Example 6B White Foam
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185 Example 6B White Solid
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186 I E:xarn ple 6 B White Solid
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187 o Example 6A White Solid
188 Example 6A White Solid
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189 Example 6A e Solid
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191 Example 6B White Foam
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Example
192 Example 6B \Vhitc Foam
193 e 6B Sticky Wax
194 Example 6B White Foam
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195 Example 6B White Foam
196 Example 6B White Foam
197 Example 6B White Foam
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198 Example 6B Sticky Wax
I ()l) e 6B White Solid
201 Example 6B White Solid
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202 Example 6B White Solid
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Example
200 Example hA \Vhitc Solid
207 Example 6A White Solid
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208 Example 6A
Colorless Oil
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209 Example 6A Cloudy
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210 Example 6A Cloudy
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211 Example 6C
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212 F Clear Film
Example 6C
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213 Example 6A Viscous Oil
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21--l- Example 6B
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216 Example 6A
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217 Example 6A
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218 Example 6B
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219 Example 6B
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220 Example 6B
221 Example 6B White Foam
222 Example 6B White Foam
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Cl Example 6A \:Vhite Foam
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225 Example 6B Opaque
Colorless Oil
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226 2:
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227 White Glass
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F Clear,
229 Example 6A
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230 Clear.
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F Colorless Oil
232 Example 5, White Semi
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234 F Example 1: Clear.
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238 F Example l; Slightly
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Example 3A: Colorless
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239 F Example l; Slightly
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Example 4A Viscous Oil
240 Example l; White Foam
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241 Example 3H ess Oil
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Example 3G
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F. Example 3G
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Example 4A Colorless Oil
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252 Example l; White
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253 Example l; Clear,
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255 Example l; Clear
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256 Example l; Clear,
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257 Example l; Clear,
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258 CH3 Example 3 L White Foam
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259 F Example l; White Foam
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260 Example l; Colorless Oil
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261 CH3 Example I: Colorless Oil
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262 Example I: Colorless Oil
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263 Example l; Colorless Oil
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Example
264 Example l; White Foam
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F Example 2A;
F Example 3A;
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F F
266 Example l; Sticky Wax
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267 Example l; Sticky .
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268 _.....CH3 Example 3 L Oil
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269 CH3 Example 31, Oil
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Example
270 e l; Colorless Oil
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271 CH3 Example I: Colorless Oil
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272 CH3 Example I: Colorless Oil
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27(-, NF Example 3F.
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277 F Example 3F·
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Example
Example 3F·
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Example 3p
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283 Example-=-3F=--I
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284 NF Example 3F· Colorless Oil
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285 F Example 3F·
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Structure Appearance
Example
Example 3F·
Example 4A
Example 3F· Colorless Oil
Example 4A
F Example 3F· White Foam
CH 3 ,,,y
? Example 4A
1/" CH3
Example 3F· yellow Stich
Example 4A Wax
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. ing
Structure Appearance
No. To
Example
290 F Example 3F· White Foam
CH3 .--,y? Example 4A
o....._
291 Example 3F· yellow Stich
Example 4A Wax
292 Example l· Colorless Oil
Example 2i
e 3A'.
Example 4A.
293 F Example I: Colorless Oil
Example 2A·
Example 3A'.
Example 4A
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
According
Structure Appearance
Example
Example 1.
Example 2A·
Example 3A:
e 4A,
----
Example-=-3F=I_
Example 4A
Example 3F· Colorless Oil
Example 4A
----------- CH
297 Example 3F·
Example 4A
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Prepared
According
Structure Appearance
Example
Example 3F·A
Example 4
Example 3F·A
CH3 ,,,,y
F Example 3p.A Colorless Oil
? Example 4
1/" CH3
Example 3F·
Example 4A
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
Structure ance
Example
Example 3F·
Example 4A
303 Example 3F.
Example 4A
--l- Example 3p.
Example 4A
305 Example 3p. Colorless Oil
Example 4A
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
According
Structure ance
Example
Example 3F·
Example 4A
307 Example 3F·
Example 4A
------
3087 F Example 3F·T___ _Thick Oil
CH3 N,,,,y Example 4A
,::;r F
309 Example 3F-A Colorless Oil
Examplc 4
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
310 Example 5, \\11ite Powder
Step 1.
311 Example 5, White Powder
Step 1.
H3C CH3
312 CH3 e 5, Cleac
Step 1. Colorless
0 Thick Oil
H2N ,, (,,
[Annotation] Mel.Chan
None set by an
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
313 F Example 5, \\11ite Powder
Step 1.
314 F Example 5 \\11ite Semi
Step 1. Solid
315 F Example 5 \\11ite Semi
Step l. Solid
316 Example 5, Clear Glass
Step 1.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
317 F Example l; Pale Purple
0 Example 2A: Sticky Wax
H2N? Example 3A:
. 0 Example 4A,
Fi- F Example 5,
step I.
318 0 e 5 Colorless Oil
Step 1.
. 0
319 Example 5. ·white Foam
Step I
320 F Example 5, White Foam
Step 1
F F
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. ing
Structure Appearance
No. To
Example
321 0 Example 5, \:Vhite Solid
Step 1
Example.:\ Colorless Oil
Step 1.
. 0
323 Example 5, Yellow Oil
Step 1.
. 0
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
324 Example 5, Yellow Oil
Step 1.
CH3 0
325 e .:\ Yellow Oil
Step 1.
. 0
CH3 0
326 Example 5, Yellow Oil
Step I.
- 0
CH3 0
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
ure Appearance
No. To
Example
327 e 5, White Foam
Step 1
328 Example 5, White Foam
Step 1
329 Example 5, White Foam
Step 1
330 Example 5, White Foam
Step 1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure ance
No. To
Example
331 F Example 5, White Foam
Step 1
332 F Example 5, Clear,
Step 1. Colorless Oil
f0 H2N , '· .,....CH3
, 0 0
.,,..,
:):):) H3C, Example 5, LightBrmrn
0 Step 1. Oil
H2N ,, f'· .,....CH3
0 0
H3C, .,....CH3
0 0
334 CH3 Example 5, Pale Yello\\
Step I. Oil
H N , '· .,....CH3
, f0 0
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd. According
Structure Appearance
No. To
Example
335 e 5, PaleYello\\
Step 1. Oil
H2N ,, (,, ,.,..CH3
0 0
336 CH3 Example 5, White
0 Step 1. PowderY
H2N ,, ('· ,.,..CH3 Solid
0 0
337 0 Example 5, Clear,
0 'CH3 Step 1. Colorless Oil
H2N ,, (,,
0 F
338 0 Example 5, White
0 'CH3 Step I. Powder.
H,N ,, (,, Solid
0 CH3
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
339 Example 5, Clear,
Step 1. Colorless Oil
340 Example 5, White Solid
Step 1.
H,N,, ?,,
.,....0
341 Example.:\ Thick Oil
0 Step 1.
H2N ,, ?,,
0 CH3
CH3H3C
342 Example 5, White Solid
Step I.
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
343 Example 5, \:Vhite Solid
Step 1.
344 Example.:\ White Solid
Step l.
345 Example 5, \:Vhite Solid
Step 1.
346 Example 5, Thick Oil
F Step 1.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
347 Example 5, e Solid
Step 1.
. 0
348 Example .:\ White Solid
Step 1.
349 Example 5, Oil
Step 1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by an
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
350 0 Example 5, Oil
Step 1
H2N ,, f,. ,.,..CH3
0 0
CH3H3C
351 CH3 Example 5, Oil
Step 1
H2N ,, f,,
CH3 ,.,..0
352 H3C, Example 5, Colorless Oil
0 Step 1
H2N ,, f,,
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure ance
No. To
Example
353 Example 5, Colorless Oil
Step 1
Example 5, Colorless Oil
Step 1
355 F Example 5, Colorless Oil
-"''Y r'l( Step 1
356 Example.:\ Colorless Oil
Step 1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. ing
Structure ance
No. To
Example
357 Example 5, Colorless Oil
Step 1
358 Example 5, Colorless Oil
Step 1
359 Example 5, Colorless Oil
Step 1
360 Example 5, Colorless Oil
Step 1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
Structure According A nce
Example
...,y F Colorless
CH3 N Foam
,,,y F
Example 5 Colorless
CH3 N Step 1 ' Foam
Example 5 Colorless Oil
Step 1 '
Example 5
Step 1 '
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
ure Appearance
No. To
Example
365 Example 5, White Foam
Step 1
H2N ,, r'·
0 CH3
366 Example 5_ Stich Wax
CH3 F Step 1.
H2N? Y
- 0 ,.,,, :::::-.,_
CH3 ,.....0 CH3
367 Example 5_ Stich Wax
0 Step l.
. 0
368 Example 5_ Stich Wax
0 Step 1.
. 0
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd. According
Structure Appearance
No. To
Example
369 Example 5 Sticky Wax
Step I.
370 Example 5 White Foam
Step 1 '
371 Example 5 White Foam
Step 1 '
372 Example 5, White Foam
Step 1
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Prepared
Structure According Appearance
Example
CH3 ('y,,,y
1/"' I
('yF Example 5 White Foam
CH3 ,,,y Step 1 '
1/"' F
Example 5 Colorless Oil
Step 1 '
Example 5 Colorless Oil
Step 1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Prepared
According
ure Appearance
Example
Example 5 Thick Oil
Step 1. ,
-r---------
379 Example 5 \Vhite Solid
Step I.
380 Example "i Thick Oil
Step 1. -,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
Structure According Appearance
Example
- -------
3;8;2 , e 5 White Foam
Step 1.
__::::::::,..,
________
383-r
F Example 5 White Solid
CH3 --···Y Step 1. ,
,:;,--- I
38--l- Example 5 \Vhite Foam
Step 1. ,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
385 Example 5, White Foam
Step 1.
386 H3C, e 5 e White
0 Step 2. Solid And
F Clear Oil
0 gH3
0 ? CH3
387 Example 5 !\latte White
Step 2. Solid And
F Clear Oil
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. ing
Structure Appearance
No. To
Example
388 Example 5, Clear,
Step 2. ess Oil
38lJ Example .:\ Colorless
Step 2. Foam
390 Example 5. Colorless
Step 2. Foam
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
391 Example 5, Clear,
Step 2. Colorless Oil
392 H3C ....__ Example 5, Semi Solid
0 Step 2.
0 F F
oc; F
393 .__ Example 5, White Foam
Step 2.
?0cH ,.,,o
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
ure Appearance
No. To
Example
394 Example 5 Colorless
Step 2. Foamy Oil
395 Example 5, White Foam
Step 2.
396 H3C, Example 5, White Foam
0 Step 2
?,,'(Jl'O
0 CH3
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure ance
No. To
397 Example 5, White Foam
F Step 2
F F
398 Example 5, \:Vhite Foam
Step 2
399 Example 5, White Foam
Step 2.
[Annotation] Mel.Chan
None set by Mel.Chan
ation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
400 H3C,oc; Example 5, White Foam
0 Step 2.
0 ? CH3 0
401 H3C, Example .:\ White Foam
0 Step 2.
«o Cl
0 ? CH3 0
402 H3C,oc; Example 5, \:Vhite Foam
0 Step 2.
0 ? CH3 0
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
403 H3C,oc; H3C, Example 5, Colorless Oil
0 0 Step 2
a F
?''·f
0 CH3
CH3 F
40--l- H3C,oc; Example 5, Colorless Oil
Step 2
a 0
?'•·f
0 CH3H3C
405 e 5, \:Vhite Foam
Step 2
ation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
406 Example 5, White Foam
Step 2
407 Example.:\ White Foam
Step 2
408 Example 5, \:Vhite Foam
Step 2
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Prepared
*Cmpd. ing
Structure Appearance
No. To
Example
409 H3C,oc; Example 5, White Foam
0 F Step 2
?''•·(o0
0 CH3 0
O 'CH3
H3C,...
410 oc; ,.,...CH3 ,.,...CH3 Example 5, White Foam
0 0 Step 2
?'-(,. 0
0 CH3
,...0
411 oc; ,.,...CH3 Example 5, White Foam
0 Step 2
?''·(o0
0 CH3
H3C,...
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
ure Appearance
No. To
Example
412 .,...CH3 .,...CH3 Example 5, Oil
0 0 Step 2
?''•?
0 CH3H3C
413 H3C, Example.:\ White Foam
0 F Step 2.
?''•?
0 CH3 ,..,O
414 H3C...._ Example 5, Thick Oil
0 CH3 Step 2.
«?'-?0
0 CH3H3C
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
415 Example 5, White Foam
Step 2.
416 Example 5, White Foam
Step 2.
417 Example 5, White Foam
Step 2.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Prepared
*Cmpd. According
Structure ance
No. To
Example
418 Example 5, White Foam
Step 2.
419 Example 5, White Foam
Step 2.
F F
420 Example 5, Colorless
Step 2. Foam
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
421 H3C, H3C, e 5, Clear,
0 0
6=; Step 2. Colorless Oil
H,,r'· 0
,,.CH3
0 0
0 CH3
H3C, ,,.CH3
0 0
422 H3C, Example 5, Clear,
0 CH3 Step 2. Colorless Oil
H,,.f
o ,,.CH3
0 CH3
,,.CH3
H3C 0
423 H3C,6=; Example 5, Colorless
0 Step 2. Foam
H,,r'· 0
,,.CH3
0 0
0 CH3
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
424 Example 5, Colorless
Step 2. Foam
42:'i Example 5, Cleac
Step 2. Colorless Oil
426 Example 5, Clear,
Step 2. Colorless Oil
ation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
427 Example 5, Clear,
Step 2. Colorless Oil
428 Example 5, White Foam
Step 2.
42lJ Example .:\ Stich Wax
Step 2.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd. According
Structure Appearance
No. To
Example
430 Example 5, Colorless Gel
Step 2
431 Example 5, Colorless Gel
Step 2
.,,,,y ?
432 Example 5, Colorless Gel
Step 2
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by an
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
433 Example 5, Colorless Gel
Step 2
43--l- Example .:\ Colorless Oil
Step 2
CH3 ?
.. ,,,y
435 H3C, Example 5, Colorless Oil
0 Step 2
0 CH3
?,, Jl .••''Y? '·( 'o
0 CH3 CH3
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
436 e 5, Colorless Oil
Step 2
437 e .:\ Colorless Oil
Step 2
438 Example 5, Colorless
Step 2 Foam
.,,,,yr)'
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
439 Example 5, Colorless
Step 2 Foam
CH3 ?
.. ,,,y
440 Example .:\ Colorless Oil
Step 2
441 Example 5, Colorless Oil
Step 2
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
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ure Appearance
No. To
Example
442 Example 5, White Foam
Step 2
443 Example 5, White Foam
Step 2.
.,,,,y ?
444 Example 5, White Foam
Step 2.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
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Structure According Appearance
No. To
Example
445 Example 5, White Foam
Step 2.
CH3 ?
..,,,y
446 Example 5, White Foam
Step 2.
447 Example 5, \:Vhite Foam
Step 2
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd. According
Structure Appearance
No. To
Example
448 Example 5, White Foam
Step 2
4lJ Example.:\ White Foam
Step 2
450 Example 5, White Foam
Step 2
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
451 Example 5, White Foam
Step 2
45.2 Example 5, Colorless Oil
Step 2
453 Example 5, Colorless Oil
Step 2
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
454 Example 5, White Foam
Step 2.
455 Example 5, White Foam
Step 2.
456 Example 5, White Foam
Step 2.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
ure Appearance
No. To
Example
457 Example 5, White Foam
Step 2.
458 Example 5, White Foam
Step 2.
459 Example 5, \:Vhite Foam
Step 2.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
460 Example 5, White Foam
Step 2.
461 Example.:\ White Foam
Step 2.
462 Example 6B. Slightly
Opaque
Colorless
Viscous Oil
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure ance
No. To
Example
463 e 6B. Slightly
Opaque
Colorless
Viscous Oil
464 Example 6B. Yellow Oil
465 Example 6B. Clear,
Colorless Oil
ation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
466 Example 6B. Pale Yello\\
467 Example 6B. Pale Yello\\
468 H3c, 0YCH3 Example 6A. Fluffy White
N6 ?,.0 Powder
?N? 'f1 'O
0 CH3H3C
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd. According
Structure Appearance
No. To
Example
469 Example 6A. Clear,
Colorless Oil
470 H3c...__ o1cH3 Example 6A. Cleac
O Colorless Oil
t'( Jl0 'o
0 CH3
471 Example 6A. Clear,
Colorless Oil
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd.
Structure According Appearance
No. To
Example
472 Example 6B. White Foam
473 O CH3 e 6B. Sticky Wax
H3C, (0
0 F F
47--l- O CH3 Example 6B. Colorless Oil
H3C, (0
? CH3
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd. According
Structure Appearance
No. To
Example
475 Example 6A. White Foam
476 Example 6B. White Foam
477 Example 6A. White Foam
ation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
478 Example 6A. White Foam
F F
479 Example 6A. \:Vhite Foam
480 Example 6B. White Foam
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
481 Example 6B. White Foam
482 O CH3 Example 6B. White Foam
H3C ....._ (0
0 CH3 0
483 O CH3 Example 6B. White Foam
H3C, (0
« Cl
0 ?0CH3 0
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd.
Structure According Appearance
No. To
Example
484 Example 6B. White Foam
485 H 3 c, 0 3 Example 6A Colorless Oil
?b 0 CH
?N? '(1'O
486 e 6A Colorless Oil
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
487 Example 6B Colorless Oil
488 Example 6A. e Foam
489 Example 6A. \Vhitc Foam
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
490 Example 6A. \\bite Wax
491 Example 6A. White Foam
492 Example 6A. White Foam
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
493 e 6B White Foam
49..J. Example 6C \:Vhitc Foam
495 Example 6A White Foam
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
1002377274
*Cmpd. Structure Prepared Appearance
No. According to
Example
496 e 6A White Foam
497 H3C O CH3 Example 6A ess
O Film
O CH3
N CH3
N O O
O CH3H3C CH3
498 Example 6A. White Foam
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd. According
Structure Appearance
No. To
Example
499 Example 6A. White Foam
500 Example 6A. \:Vhite Foam
501 Example 6A. White Foam
502 Example 6A. White Foam
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
503 Example 6A. White Foam
504 Example 6A. White Foam
F F
505 e 6A. Clear,
Colorless Oil
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd. According
Structure ance
No. To
Example
506 H3c, 0 CH3 Example 6A. Clear,
Y Colorless Oil
? ?,,
?N>y 'f1'O
0 CH3
507 Example 6A. Clear,
Colorless Oil
508 Example 6A. Clear,
Colorless Oil
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
*Cmpd. According
Structure Appearance
No. To
Example
509 Example 6A. Clear,
Colorless Oil
510 Example 6A. Cleac
Colorless Oil
511 Example 6A. Clear,
Colorless Oil
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
512 Example 6A. Clear,
Colorless Oil
513 Example 6B. Clear,
Colorless Oil
514 Example 6B. Clear.
Colorless Oil
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
515 Example 6B. Clear,
Colorless Oil
516 Example 6B. Clcac
Colorless Oil
517 e 6B. Clear,
Colorless Oil
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
518 Example 6B. Clear,
ess Oil
519 Example 6B. Clear,
Colorless Oil
520 Example 6B. Clear.
Colorless Oil
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure ing Appearance
No. To
Example
521 Example 6A. White Foam.
522 Example 6A. Stich White
523 Example 6A Colorless Oil
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
524 Example 6A ess Oil
525 Example 6A Colorless Oil
526 Example 6A Colorless Oil
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
527 Example 6A Colorless
CH3 ?
..,,,y
Example 6A Colorless
CH3 ?
..,,,y
529 Example 6A Colorless
[Annotation] an
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
530 Example 6A Colorless
531 Example 6A Colorless Oil
532 Example 6A Colorless Oil
..,,,yrY
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by an
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
533 Example 6A Colorless Oil
53--l- Example 6A Colorless Oil
535 Example 6A. \:Vhite Foam
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd.
Structure According Appearance
No. To
Example
536 Example 6A. White Foam
CH3 ?
..,,,y
S-37 Example 6A. White Foam
538 Example 6A. \:Vhite Foam
CH3 ?
__,,,y
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure Appearance
No. To
Example
539 Example 6A. White Foam
540 Example 6A. White Foam
541 Example 6A. White Foam
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. ing
Structure ance
No. To
Example
542 H30\OH3CYO Example 6A. White Foam
l H
\ N
N ,
543 Example 6A. White Foam
Example 6A. White Foam
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
*Cmpd. According
Structure ance
No. To
Example
545 Example 6A. White Foam
546 Example 6A. White Foam
547 Example 6A White Foam
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
* C132)pd. .
Structure Achcligdmg Appearance
Example
548 H3C\O OYCHS Example 6A. White Foam
/ o
I H
\ N,,
N " O
0 CH3
549 H3,C\O OYCHB e 6A. White Foam
O CH 3
/ 0 CH3
l H
\ N h ‘\\\
N O ‘
0 CH3
U1 ‘Ji 0 I 03O O OI w Example 6A. White Foam
O o_/<
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
* Cmpd. According
Structure ance
No. To
Example
55 l H3C \ Example 6A. White Foam
552 HSC
\ Example 6A. White Foam
UI Ul U) Example 6A Colorless
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Prepared
* Cmpd. According
Structure ance
No. To
Example
554 H C\3 O CH Colorless
3 e 6A
O Y Foam
/ O
\ N,,
N " O
0 CH3
>“Cmpd. No. — Compound Number
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Table 2. ical Data
Cmpd. MP IR NMR
No. (CC) (c1111) (‘H, ”C, 19F)
‘H NMR (500 MHz. CDCL.) 5 7.53 4
7.41 (m, 4H), 7.32 4 7.23 (m. 4H), 7.23 4
HRMS—ESI 7.13 (m, 2H), 6.01 (q, J: 6.3 Hz, 1H),
(m z) 4.98 (d. .1: 8.0 Hz. 1H). 4.13 (p. .1: 7.1
My Hz. 1H). 2.78 (s. 1H). 1.41 (s. 9H). 1.21
calcd for (d, J: 6.3 Hz, 3H). 0.53 (d, J: 7.3 Hz.
C23H29N05, 3H)
399.2046;
found, ”C NMR (126 MHz, CDC13)5 172.55,
48 154.95,145.04.142.56, 128.32, 125.30.
127.17.127.11.125.59. 125.52.79.83.
79.54. 75.16. 49.13. 28.29. 17.95. 14.38
1H NMR (400 MHz, CDC13) 5 7.42 —
7.07 (m, 10H), 5.80 (dq,J= 10.1, 6.1 Hz,
1H). 4.97 (d. .1: 8.0 Hz. 1H). 4.19 4 4.06
(m, 1H), 4.03 (5,1: 101 Hz. 1H), 1.41
ESIMS (s, 9H), 1.23 (d, J: 6.1 Hz. 3H), 0.76 (d,
2 m z 3845 .1: 7.2 Hz. 3H)
(1M+HJ+)
13C NMR (101 MHz, CDC13) 5 172.83.
154.96,141.52,141.26, 128.79, 128.50.
128.10. 128.08. 126.91. 126.67. 73.10.
57.98. 28.33, 19.31.1798
1H NMR (400 MHz, CDClg) 5 7.22 —
7. 15 (m. 2H). 7.00 (ddd. .1: 3.5. 1.2. 0.6
Hz. 1H). 6.97 4 6.89 (m. 3H). 5.52 (dq, .1
= 7.3. 6.2 Hz, 1H). 4.99 (d, J: 5.1 Hz.
ESIMS 1H). 4.63 (d. J: 7.3 Hz. 1H), 4.29 — 4.18
m z 396.5
. (m. 1H). 1.43 (s. 9H). 1.28 (d. .1: 6.2 Hz.
3 " ([M4Hr) 3H). 1.04 (d, J: 7.2 Hz, 3H)
13C NMR (101 MHz. CDC1~.) 5 172.64.
143.87. 142.87, 126.75. 126.55. .
125.39. 124.58. 124.56, 79.69. 74.40,
4931.47.46, 28.32, 15.74. 18.22
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 5 7.31 4
7.16 (m, 4H), 6.97 (td, J: 8.7, 7.0 Hz,
4H), 5.71 (dq, .1: 9.8. 6.1 Hz, 1H). 4.95
ESIMS (d, J : 8.0 Hz, 1H), 4.22 4 4,07 (m, 1H),
m/Z 420.6 4.03 (d, J: 9.8 Hz, 1H), 1.42 (s, 9H),
([M+H]+) 1.22 (d, .1: 6.2 Hz, 3H). 0.84 (d. .1: 7.2
Hz, 3H)
19F NMR (376 MHz, CDC13) 5
411594
1H NMR (400 MHz, CDC13) 5 7.37 4
7.19 (m, 10H), 6.01 4 5.89 (m, 1H), 5.02
ESIMS (d, .1: 7.9 Hz, 1H), 4.27 4 4.10 (m. 1H),
m z 450.6 3.38 (dq. .1 : 8.96.9 Hz, 1H), 3.25 4
([M+Na]+) 3.13 (m, 1H), 1.40 (d, J: 2.1 Hz, 9H),
1.18 (t, J: 7.0 Hz, 3H), 1.15 4 1.06 (m,
1H NMR (400 MHz, CDC13) 5 7.38 4
ESIMS 7.21 (m, 10H), 6.01 4 5.82 (m, 1H), 5.01
6 m z 4366 (d, .1: 8.0 Hz, 1H), 4.27 4 4.12 (m. 1H),
(1M4Nar) 3.15 (s, 3H). 1.40 (s. 9H), 1.15 4 1.07 (m,
1H NMR (400 MHz, CDC13) 5 7.36 (td, J
: 8.5, 6.1 Hz, 1H), 7.26 4 7.15 (m. 1H),
6,914 6.68 (m, 4H), 5.86 4 5.73 (m, 1H),
4.92 (d,J= 8.0 Hz, 1H), 4.66 (d, J: 10.1
[52521655, Hz, 1H). 4.23 4 4.09 (m, 1H), 1.42 (s,
7 9H), 1.27 (d, .14 6.1 Hz, 3H)
19F NMR (376 MHz, CDC13)5
41 1 1.06 (d_ .1: 7.6 Hz), 41 1 1.55 (51.1:
75 Hz), 411 1,91 (dd, J: 7,9, 2.7 Hz), 4
112.72 (d, J: 5.9 Hz)
1H NMR (400 MHz. CDCL.) 5 7.48 4
7.41 (m. 4H), 7.38 4 7.19 (m, 6H). 5.97
(dq, J: 25.6, 6.5 Hz, 1H), 4.90 (d, J:
ESIMS 7.8 Hz, 1H), 4.23 4 4.05 (m, 1H), 1.41 (s,
8 m z 424.5 9H), 1.29 (dd, .1: 6.5. 1.0 Hz, 3H). 0.75
([M4Nar) (d, J : 7.2 Hz, 3H)
”P NMR (376 MHz. CDCL) 5
4169.03
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NIVIR
N0. (‘0 (cm'l) (1H, 13C. 191:)
1H NMR (400 MHz. CDC13) 5 7.22 4
7.09 (m. 4H). 6.91 4 6.65 (m. 4H). 5.70
(dq. .1: 9.8. 6.1 Hz. 1H). 4.94 (d. .1: 8.0
Hz. 1H). 4.19 4 4.05 (m. 1H). 3.93 (d.J:
ESIMS 9.8 Hz. 1H). 3.76 (s. 3H). 3.74 (s. 3H).
m 2 444.6 1.42 (s. 9H). 1.21 (d. .1: 6.2 Hz. 3H).
(| M+H 1+) 0.83 (d. .1: 7.2 Hz. 3H)
”C NMR (101 MHz. CDC13) 5 172.84.
158.34. 158.22. 133.99. 133.81. 128.96.
. 113.84. 79.64. 73.33. 56.17.
55.22. 49.22. 28.31. 19.28. 18.19
1H NMR (400 MHz. CDC1~,) 5 7.33 4
7.21 (m. 2H). 7.14 4 7.02 (111.2H). 7.03 4
6.84 (m. 4H). 5.72 (dq. J: 2 Hz.
ESIMS 1H). 4.93 (d. .1: 8.0 Hz. 1H). 4.22 4 4.07
m 2 420.6 (m. 1H). 4.03 (d. .1: 9.8 Hz. 1H). 1.42 (s.
(UVHHY) 9H). 1.24 (d. J: 6.2 Hz. 3H). 0.84 (d. J:
7.1 Hz. 3H)
”P NMR (376 MHz. CDCL.) 5
-112.14. -112.59
1H NMR (400 MHz. CDC13) 5 7.33 4
7.11 (m. 8H). 5.71 (dq. .1: 10.0. 5.9 Hz.
1H). 4.94 (d. J: 8.0 Hz. 1H). 4.18 4 4.07
(m. 1H). 3.99 (d, J: 9.9 Hz. 1H). 1.42
ESIMS (d. .1: 1.7 Hz. 9H). 1.24 (d. J: 6.2 Hz.
m Z 452.5 3H). 0.87 4 0.81 (111.3H)
([M+H]+)
”C NMR (101 MHz. CDC13) 5 172.79.
154.94. 142.68. 142.43. 134.73. 134.43.
130.21.129.93.128.39. . 127.49.
127.18. 126.28. 126.20. 79.79. 72.40.
57.09. 49.15. 28.30. 19.21.18.04
1H NMR (400 MHz. CD0.) 5 7.79 4
7.72 (m. 2H). 7.72 4 7.62 (m. 1H). 7.59 4
ESIMS
7.48 (m. 1H). 7.46 4 7.36 (m. 2H). 7.36 4
m 2 382.5
12 7.25 (m. 2H). 5.81 4 5.64 (m. 1H). 5.09
([M+H1+)
(s. 1H). 4.55 4 4.34 (m. 1H). 4.33 4 4.18
(m. 1H). 1.46 (s. 9H). 1.45 (d. J: 3.5 Hz.
3H). 0.70 (d. .1: 6.3 Hz. 3H)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. ”C. 191:)
1H NMR (400 MHz, CDC13) 5 7.33 4
ESIMS 7.21 (m, 4H), 7.15 4 7.04 (m, 4H), 5.15 4
m z 398.6 5.03 (m. 1H). 5.01 (d. .1: 8.0 Hz. 1H).
([M4Hr) 4.35 4 4.24 (m, 1H), 4.27 4 4.15 (m, 1H).
1.44 (s, 9H), 1.29 (d, J: 7.2 Hz, 3H),
1.03 (d. .1: 6.4 Hz. 3H)
1H NMR (400 MHz. CDCL.) 5 7.46 4
ESIMS 7.36 (m, 4H). 7.17 4 7.07 (m, 4H), 5.71
m z 5425 (dq, J: 9.7, 6.2 Hz, 1H), 4.91 (d, J: 7.9
(|M+Hr) Hz. 1H). 4.13 (p. .1: 7.2 Hz. 1H). 3.97
(d, J : 9.8 Hz, 1H). 1.42 (s, 9H), 1.22 (d,
J: 6.1 Hz, 3H), 0.86 (d, J: 7.2 Hz, 3H)
1H NMR (400 MHz. CDC];) 5 6.73 (d. J
: 3.4 Hz. 1H). 6.67 (d. .1: 3.4 Hz. 1H).
ESIMS 6.59 4 6.46 (m, 2H), 5.43 (dq, J: 7.4, 6.2
m z 4245 Hz, 1H), 5.03 (d, J: 8.1 Hz, 1H), 4.42
(|M+Hr) (d. .1: 7.3 Hz. 1H). 4.24 (p. .1: 7.1. 6.7
Hz, 1H), 2.41 (5,1: 1.1 Hz, 3H), 2.40
(d,J= 1.1 Hz, 3H), 1.43 (s, 9H), 1.27 (d,
.1: 6.2 Hz. 3H). 1.09 (d. .1: 7.1 Hz. 3H)
1H NMR (400 MHz. CDCL.) 5 7.18 4
ESIMS (11:, 4H). 7.11 4 7.02 (m, 4H), 5.75
(dq.J— 10.2, 6.2 Hz, 1H). 4.95 (d, J—
16 ”1511346 8.0 Hz. 1H). 4.1 1 (p. .1 : 7.4. 6.5 Hz. 1H).
(1 J )
3.95 (d,J: 10.0 Hz, 1H), 2.27 (s, 3H),
2.25 (s, 3H), 1.41 (s, 9H), 1.22 (d, J: 6.1
Hz. 3H). 0.80 (d. J: 7.2 Hz. 3H)
1H NMR (400 MHz. CDCL.) 5 7.55 (d, .1
= 8.1 Hz, 2H), 7.41 (d, J: 8.0 Hz, 2H),
7.314 7.16 (m. 5H), 5.82 (dq.J= 9.9.6.2
7773334154286 Hz. 1H). 4.92 (d. .1: 7.9 Hz. 1H). 4.15 4
18 4.06 (m, 2H), 1.41 (s, 9H), 1.24 (d, J4
([M+H]+)
6.2 Hz, 3H), 0.77 (d, J: 7.2 Hz, 3H)
”P NMR (376 MHz. CDC];) 5
-62.58
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NIVIR
N0. (‘0 (cm'l) (1H, 13C. 191:)
1H NMR (400 MHz, CDClg) 8 7.30 4
7.22 (m, 4H), 7.22 4 7.15 (m, 4H), 5.71
(dq, .1: 9.6, 6.2 Hz, 1H), 4.91 (d, .1: 8.0
Hz, 1H),4.214 4.06 (m, 1H), 4.00 (d, J:
ESIMS
9.8 Hz, 1H), 1.42 (s, 9H), 1.22 (d, J: 6.2
m 2 4525
19 Hz, 3H), 0.85 (d, J: 7.2 Hz, 3H)
(| M+H r)
13C NMR (101 MHz, CDC13) 8 172.75,
154.96, 139.41, 139.25, 133.03, 132.77,
129.43, 129.35, 129.05, 128747981,
7251, 56.45, 49.17, 28.30, 1918,1809
1H NMR (400 MHz, CDClg) 8 7.25 4
7,14 (m, 4H), 7.06 4 6,87 (111,4H), 5,68
(dq, .1: 9.3, 6.2 Hz. 1H), 4.83 (s, 1H),
4.02 (d, J: 93 Hz, 1H), 3.82 (dd, J:
18.2, 5.9 Hz, 1H), 3.56 (dd,J= 18.2, 5.2
ESIMS Hz, 1H), 1.43 (s, 9H), 1.22 (d, .1: 6.2 Hz,
m 2 406,5 3H)
13C NMR (101 MHz, CDC1~,) 8 16966,
161.74 (d, .1:245.9 Hz), 161.63 ((1.1:
245.7 Hz), 155.45, 136.74, 129.65 (d,J=
7.9 Hz), 115.70 (d,J= 21.3 Hz), 11541
(d, .1: 21.2 Hz), 79.97, 77.21, 73.15,
5584, 42.44, 28.29, 19.17
1H NMR (400 MHz, CDClg) 8 7.30 4
7,15 (m, 4H), 7.06 4 6,89 (m, 4H), 5,75 4
.62 (m, 1H), 4.90 (d, .1: 8.4 Hz, 1H),
4.11 (q, J: 67 Hz, 1H), 4.03 (d, J: 9.8
ESIMS Hz, 1H), 1.494 1.33 (m, 10H),1.30—
m 2 434.6 1.08 (m, 4H), 0.54 (t, .1: 7.4 Hz, 3H)
13CNMR (101 MHz, CDC13) 8 172.10,
161.70 (d, .1: 245.6 Hz), 155.20, 136.97,
129.52, 115.7l(d,.1:21.3 Hz), 115.44
(d,J= 21.2 Hz), 79.73, 73.12, 56.08,
54.46, 28.30, 25.40, 19.26, 8.95
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR Nh/IR
N0. (‘0 (cm'l) (1H, 13C. 191:)
1H NMR (400 MHz, CDC13) 5 7.30 4
7.15 (m, 4H), 7.04 4 6.91 (m, 4H), 5.69
(dq. .1: 9.7.6.1 Hz. 1H). 4.86 (d. .1: 9.3
Hz, 1H), 4.09 (dd, J : 9.3, 4.2 Hz, 1H),
4.03 (d, J: 9.8 Hz, 1H), 1.69 4 1.57 (m,
1H). 1.42 (s. 9H). 1.21 (d. .l:6.2 Hz.
ESIMS
3H). 0.73 (d. .1: 6.9 Hz. 3H). 0.43 (d. .1:
m 2 448.6
22 6.8 Hz, 3H)
([M—1—H]+)
”C NMR (101 MHz. CD(‘,1~,)5 171.77.
161.73 (d,J: 246.0 Hz), 155.60, 137.05,
129.61,129.52,129.44,115.71(d,J=
21.6 Hz). 11549 (d. .1: 21.4 Hz). 7969.
73.23. 58.49. 56.03. 30.92. 28.28. 19.31.
18.96, 16.54
1H NMR (400 MHz, CDC13) 5 7.30 4
7.20 (m. 4H). 7.04 4 6.92 H). 5.68
(dq, .1: 9.8, 6.2 Hz, 1H), 4.72 (d, J: 8.9
Hz, 10 (td,J= 9.2, 5.1 Hz, 1H),
4.02 (d. .1: 10.0 Hz. 1H). 1.41 (s. 9H).
1.22 (d. .1: 6.1 Hz. 3H). 0.96 (ddd. .1:
ESIMS 13.7, 9.6, 5.5 Hz, 1H), 0.84 (m, 1H). 0.75
m 2 462.7 (d, J: 6.5 Hz, 3H), 0.70 (d, J: 6.6 Hz,
(| M+H |+) 3H)
”C NMR (101 MHz, CDC13) 5 173.06,
161.72 (5.1: 245.8 Hz). 155.29. 137.17.
136.83. 129.49. 115.73 (d../: 21.4 Hz).
115.46 (d, J: 21.3 Hz), 79.74, 73.02,
56.27, 52.04, 41.48, 28.28, 24.41, 22.76,
21.53. 19.23
(Thin
?lm) HRMS-ESI 1H NMR (300 MHz, CDC13)8 7.50 4
3358. (m z) 7.37 (m. 1H). 7.29 4 7.19 (m. 1H). 7.20 4
2977. |M+Nar 7.06 (m. 2H). 6.92 4 6.75 (m. 4H). 5.91
1708 calcd for (dq,J= 10.1.6.4 Hz, 1H), 5.03 4 4.97
1491, C25H33NN€1064 (m, 1H), 4.98 (d, J: 9.9 Hz, 1H), 4.22 4
1243. 466.22; 4.04 (m. 1H). 3.84 (s. 3H). 3.76 (s. 3H).
1162, found, 1.41 (s, 9H), 1.23 (d, J : 6.2 Hz, 3H),
1051, 466.2191 0.82 (d,J= 7.2 Hz, 3H)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
(Thin 1H NMR (300 MHz, CDClg) 5 7.18 (dt, J
?lm) 111137178581 = 11.8, 7.9 Hz, 2H), 6.89 (dq, J: 7.6, 1.5
3368. Hz. 2H). 6.83 (dt. J: 4.0, 2.1 Hz. 2H).
| M+Nal+
2978, 6.71 (dddd, J: 10.7, 8.2, 2.6, 0.9 Hz,
calcd for
1707, 2H), 5.77 (dq, J: 10.2, 6.1 Hz, 1H), 4.96
OH «NNaO
1597. 3456 22, 6’ (d. .1: 8.0 Hz, 1H). 4.20 4 4.01 (m. 1H),
1488. fou11d‘ 3.96 (d. .1: 10.3 Hz. 1H). 3.77 (s. 3H).
1156, 3.75 (s, 3H), 1.42 (s, 9H), 1.24 (d,J= 6.2
466 2193
1043 ' Hz, 3H), 0.79 (d, J: 7.2 Hz, 3H)
(Thin 38! 1H NMR (300 MHz. CDCL.) 5 7.14 4
7.02 (m, 2H), 6.99 4 6.84 (m, 4H), 5.67
?lm) 3368 ([M+H]+)
(dq, J: 9.8, 6.2 Hz, 1H), 4.95 (d, J: 7.9
‘ mlcd‘
Hz, 1H). 4.22 4 4.05 (m, 1H). 3.94 (d. .1:
26 I?” “?led for
9.8 Hz. 1H). 2.20 (d. J : 2.1 Hz. 3H).
?g; C25§;6F§T1§?O4= 2.19 (d, J: 2.2 Hz, 3H), 1.42 (s, 9H),
' ‘ 1.284 1.17 (m, 3H). 0.86 ((1.1: 7.2 Hz.
1032 found,
470.2122 ‘3 H)
(Thin 1111371782331 1H NMR (300 MHz, CDC13) 5 7.22 (dd, J
: 4.6, 1.9 Hz, 2H). 7. 13 (t, .1: 7.9 Hz.
?lm) (1M+HJ+)
2H), 7.04 (ddd,J: 7.6, 5.1, 1.9 Hz, 2H),
3366 calcd
27 2978’ 5.67 (dq, J: 10.0, 6.2 Hz, 1H), 4.96 (d,J
calcd for
1706 : 7.9 Hz. 1H). 4.22 4 4.05 (m, 1H). 3.91
(,er CleNaO4‘
“62‘ ’5‘ 562
1,22, (5.1: 9.9 Hz, 1H), 2.31 (s, 3H). 2.29 (s,
1051’ fo1u1d * 3H), 1.42 (s, 9H), 1.22 (52.1: 6.0 Hz,
33 3H), 0.87 (d,J= 7.2 Hz, 3H)
(1:11;; ”1127475231381 1H NMR (300 MHz, CDCl;) 5 7.45 4
7.37 (m, 4H), 7.26 4 7.18 (m, 4H), 5.75
3285 [M+Na]+
2979’ (dq. J: 10.0, 6.1 Hz. 1H). 4.91 (d. .1:
(?led for
28 2107‘ 7.9 Hz, 1H). 4.20 4 4.06 (m, 1H). 4.04 (d,
C) H“ NNaO
1702’ {5:989 4’ J: 9.9 Hz, 1H), 3.05 (s, 1H), 3.04 (s,
1501’ d 3 1H) 1.42 (s, 9H), 123 (5:1: 6.2 Hz,
3H). 0.82 (d. .14 7.2 Hz, 3H)
1160 4541993
(Thin HRMS—ESI 1H NMR (300 MHz, CDC13) 5 7.22 4
?lm) (777 z) 7.16 (m, 4H). 7.13 4 7.03 (m, 4H), 5.76
3362. |M+Nar (dq. .1: 10.2, 6.1 Hz. 1H). 4.95 (d. .1:
2964, calcd for 7.8 Hz, 1H), 4.17 4 4.02 (m, 1H), 3.96 (d,
1712, C27H3-NNaO4, J: 10.2 Hz, 1H), 2.67 4 2.45 (m, 4H),
1510. 4622615; 1.41 (s, 9H). 1.23 (d. .1: 6.2 Hz. 3H).
1163. found, 121 4 1,10 (m, 6H). 0.73 (d. .1: 7.2 Hz.
1053 462.2622 3H)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR
MASS NMR
N0. (‘0 (cm'l) (1H. 13C. 191:)
1H NMR (400 MHz. CDC13) 5 7.32 —
7.20 (m. 6H). 7.20 — 7.14 (m. 1H). 6.97
(1. .1: 8.7 Hz. 2H). 5.75 (dq. .1: 10.0.6.2
Hz. 1H). 4.92 (61.1: 8.0 Hz. 1H).4.11(t.
J: 7.4 Hz. 1H). 4.02 (d. J: 10.0 Hz.
ESIMS 1H). 1.41 (s. 9H). 1.23 (d. .l:6.2 Hz.
m Z 402.6 3H). 0.77 (d. .1: 7.2 Hz. 3H)
([M+H]+)
”C NMR (126 MHz. CDC13) 5 172.81.
161.71 (d. .1:245.7 Hz). . 141.23.
137.03 (d. J: 3.5 Hz). 129.56 (d. J: 7.9
Hz). 128.59. 127.99. 126.82.115.62(d.J
: 21.3 Hz). 79.70. 72.94. 57.09. 49.16.
28.31. 14.13
1H NMR (400 MHz. CDC13) 5 7.58 (t. J
= 2.1 Hz. 2H). 7.38 (dd. J: 8.4.3.9 Hz.
2H). 7.29 4 7.25 (m. 1H). 7.20 (dd. .1:
8.5. 2.2 Hz. 1H). 5.84 (q. J : 6.2 Hz. 1H).
4.94 (d. J: 7.8 Hz. 1H). 4.14 (t. J: 7.4
Hz. 1H).3.05 (s. 1H). 1.41 (s. 9H). 1.18
ESIMS
(d. .1: 6.3 Hz. 3H). 1.00 (d. .1: 7.2 Hz.
DJ U) 96
(1M-H201+) 3H)
”C NMR (126 MHz. CD(‘,1~.)5 172.37.
155.04. 144.43. 142.16. 132.90 (d.J:
2.7 Hz). 131.93. 131.87. 130.51. 130.46.
. 127.70. 125.08. 124.99.80.20.
78.55. 74.10. 49.16. 34.67. 28.25. 14.28
1H NMR (400 MHz. CDC13) 5 7.37 —
7.28 (m. 4H). 7.18 (ddd. J: 8.4. 2.2. 0.8
Hz. 1H). 7.09 (ddd. J: 8.4.2.209 Hz.
1H). 5.86 (q. J: 6.2 Hz. 1H). 4.93 (d. J:
7.8 Hz. 1H). 4.14 (t. J: 7.4 Hz. 1H).
3.06 (s. 1H). 1.41 (s. 9H). 1.18(d..1:6.3
Hz. 3H). 0.98 (d. .1: 6.8 Hz. 3H)
ESIMS
m 2 486.5 ”C NMR (126 MHz. CDC13) 5 172.28.
(I M-HzOF) 158.09 (d. .1: 249.9 Hz). 158.06 (d. .1:
2495 Hz). 155.05.145.31(d..1: 5.7
Hz). 142.98. 130.64 (d. J: 10.0 Hz).
121.90 (d. .1: 8.8 Hz). 120.38 (d. .1:
12.3 Hz). 120.24 (d. .1: 12.3 Hz). 114.59
(d. J: 22.6 Hz). 114.20 (d. J: 22.9 Hz).
8019. 78.60. 74.13. 49.13. 34.67. 28.25.
14.30
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by an
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
1H NMR (400 MHz, CDC13) 5 7.24 (dd, J
= 10.4, 8.1 Hz, 2H), 7.09 (dd,J= 5.5, 2.2
Hz, 2H), 7.02 (td, J: 86,23 Hz, 2H),
,69 (dq,J: 10.1, 6.1 Hz, 1H), 4.94 (d,J
= 7.9 Hz, 1H), 4.13 (t, J: 7.5 Hz, 1H),
3,92 (d, .1: 10.0 Hz, 1H), 2.33 (s, 3H),
ESIMS 2.31 (s, 3H), 1.42 (s, 9H), 1.21 (d, .1: 6.1
m 2 4806 Hz, 3H), 0.84 (d, J: 7.2 Hz, 3H)
([MT)
"C, NMR (126 MHz, CD(‘,1~,) 5 172.81,
154.92, 139.66, 139.44, 136.53, 136.10,
133.08,132.72,130.69, 130.57, 129.43,
129.12, , 126.46, 79.77, 7261,
5649,4917, 28.29, 20.16, 20.09, 19.23,
1H NMR (300 MHz, CDC13_) 5 7.82 (ddd,
(Thin
.1: 8.6, 7.3, 1.8 Hz, 1H), 7.51 (a, .1: 7.9,
Hz, 1H), 73 4 7.12 (m, 3H), 7.09
2980, (td, J: 7.6, 1.4 Hz, 1H), 6.94 (dd, J:
36 1669’ 8,1, 1.4 Hz, 1H), 6.90 (dd, .1: 8.1, 14
1486‘ Hz, 1H), 6.23 (qd, .1 : 6.3, 1.6 Hz, 1H),
”52’ 5.02 (d, J: 79 Hz, 1H), 4.30 — 4.13 (m,
1H), 3.21 (s, 1H), 1.42 (s, 9H), 1.26 (d, J
1160 {,7
: 6.2 Hz, 3H), 1.07 (d, .1: 7.2 Hz, 3H)
(Thin
3375,
2981,
1703, 1 ,
1609 HNMR(500_MHz, CDC13)8 7.18 —
1515’ 6,9] (m, 6H), 5.63 (dq, .1: 9.4, 6.2 Hz,
1573‘ HRMS-ESI 1H), 4.92 (d, .1: 8.0 Hz, 1H),4,241 4 4.06
1433? (m z) (m, 1H), 3.98 (d,J= 9.5 Hz, 1H), 1.42 (s,
1380’ [M+Na] 9H), 1.23 (d, J: 6.1 Hz, 3H), 0.91 (d, J:
calcd for 7.2 Hz, SH)
___ 1:367‘
1284‘ C23H35F1NNaO1,
1250’ 478.1612; F N1V_IR (471 MHz, CDC13) 5
1208 found, 43625 (dt, .1: 20.6, 9.7 Hz),
4781624 43669 (dt, .1: 20.4, 9.9 Hz),
11 62‘
“13> -139.30(dd,J=21.3,10.5Hz),
105?; -139.70(dd,J=21.1,10,1Hz)
1023, 967,
909, 873,
821, 754,
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS.
N0. (0C) (cm'l) (H. 13C. 191:)
(Thin
3440.
2981.
1704.
128(7) 1H NMR (300 MHz. CDC];) 5 7.32 4
1452‘ HRMS-ESI 7.22 (m. 2H). 7.18 4 7.02 (m. 4H). 5.64
13'79’ (m z) (dq. J: 9.6. 6.2 Hz. 1H). 4.93 (d. J: 8.0
1367, [M+Na] Hz. 1H). 4.25 4 4.03 (m. 1H). 3.98 (d. J:
calcd for 9.6 Hz. 1H). 1.42 (s. 9H). 1.23 (d. .1: 6.2
___ 1306‘
- C33H25C13F3NNaO4. Hz. 3H). 0.92 (d. J = 7.2 Hz. 3H)
1250.
510.1021;
found. W
F NMR (471 MHz. CDC];) 0a
1 162‘
_‘ 510.1033 -116.98(q.J:6,9 Hz).-117,44(q.J:
1095.
6 8 Hz)
1054. '
1023. 907.
867. 822.
799. 780.
731. 719.
(Thin
3364.
2980.
2931. 1HNMR (300 MHz. CDC13) 5 7.13 —,, ,,
”97‘ 6.98 (m. 4H). 6.90 (td. .1: 9.1. 7.4 Hz.
1%01‘ HRMS-ESI 2H). 5.67 (dq. J: 10.1.6.1Hz. 1H). 4.93
14513 (m z) (d. J: 8.0 Hz. 1H). 4.22 — 4.02 (m. 1H).
”'79’ [M+Na] 3.91 (d. .1: 10.1 Hz. 1H). 2.23 (d. .1: 2.0
1366‘ calcd for Hz. 3H). 2.21 (d. J: 2.0 Hz. 3H). 1.42 (s.
39 ___
1307’ F3NNaO4. 9H). 1.21 (d. J: 6.1 Hz. 3H). 0.83 (d. J:
’ 470.2113; 7.2 Hz. 3H)
1248..
found.
1 207
470.2120 w
1163‘ F NMR (471 MHz. CDC13) oA
’ -119.99 (q.J=6.8 Hz). -120.57 (q.J=
1118.
7 0 Hz)
1052. ‘
1023. 959.
908. 881.
821. 781.
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 5 7.53 (ddd.
J: 13.6, 6.7, 4.2 Hz, 8H), 7.45 — 7.37
(m. 8H). 7.35 4 7.29 (m. 2H). 5.87 (dq../
: 12.3. 6.1 Hz. 1H), 4.94 (d,J: 7.1 Hz,
1H), 4.18 — 4.09 (m, 2H), 1.41 (s, 9H),
ESIMS 1.31 (d. .1: 6.2 Hz. 3H). 0.80 (d. .1: 7.1
m z 536 Hz, 3H)
40 ___ ___ +)
”C NMR (126 MHz, CDC13) 5 172.93.
154.96. 140.72. 140.60. 140.56. 140.21.
139.92,139.68,128.76, 128.75, 128.51,
127.58,127.30,127.27, 127.23, 127.00,
126.96. 79.70. 73.12. 57.33. 49.22. 28.31.
19.39. 18.04
1H NMR (400 MHz, CDC13) 5 7.38 (1..)
= 8.1 Hz, 2H), 7.32 (dd, J: 13.6, 2.1 Hz,
2H). 7. 10 (dd. .1: 8.4. 2.1 Hz. 1H). 7.07
HRMS-ESI (dd. J: 8.4.2.1Hz, 1H). 5.65 (dq, J:
(m z) 9.5, 6.2 Hz, 1H), 4.93 (d, J: 7.9 Hz, 1H),
[M+Na1+ 4.22 4 4.09 (m. 1H). 3.97 (d. J: 9.5 Hz.
calcd for 1H). 1.42 (d. .1: 0.9 Hz. 9H). 1.24 (d. .1:
C33H25C14NNaO4, 6.1 Hz. 3H), 0.93 (d, J: 7.2 Hz, 3H)
542.0430;
found. ”C NMR (126 MHz. CD(‘,1~.)8 172.73.
542.0442 154.93,140.37,140.26, 133.10, 132.76,
131.66,131.34,130.97,130.67,130.23,
130.06. 127.34. . 79.92. 71.96.
55.79. 49.16. 28.29.1914. 18.11
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. 13C. 191:)
1H NMR (400 MHz, CDC13) 8 7.38 —
7.28 (m, 2H), 7.06 (dd, J: 10.0, 1.8 Hz,
1H). 7.04 4 6.94 (m. 3H). 5.66 (ddt. .1:
9.1, 6,9, 5.5 Hz, 1H), 4.92 (d,J: 8.0 Hz,
1H), 4.22 — 4.08 (m, 1H), 4.01 (d, J: 9.4
HRMS—ESI Hz. 1H). 1.42 (d. .1: 1.3 Hz. 9H), 1.24
(m z) (dd. .1 : 6.2. 1.3 Hz. 3H). 0.92 (d. .1: 7.2
[M41921]+ Hz, 3H)
calcd for
44 ___ ___ i
hFZNNdm. "C NMR (126 MHz. CD(‘,1~,)5 172.68.
510.1021; 158.17(d,J:250,1Hz),158,03(d,J:
found, 250.1 Hz), 154.93, 141.08 (d, J: 6.1
510.1030 Hz). 140.95 (d..I:6.1Hz). 131.11.
130.80. 12451 (d. .1: 3.3 Hz). 124.36 (d.
J: 3.6 Hz), 120.08 (d, J: 17.6 Hz),
11978 (d, J: 17.6 Hz), 11648 (d, J:
16.8 Hz). 116.24. 79.92. 72.02, 56.07.
49.15,28.28,19.10,18.10
ESIMS
m z 300
4i ___ ___ ___
‘ (lM+HJ+)
ESIMS
m Z 284.3
(1M+H1+)
ESIMS
mwz 296.3
(119141110
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, 13C, 191:)
(Thin
3395,
2885,
1741,
1603,
1508, HRMS-ESI 1H NMR (400 MHz, CD(713)5 8.55 (s,
1459, (m 2) 3H), 7.22 (dt, J: 9.0, 4.8 Hz, 4H), 6.98
1381, ([M+H]+) (q,J= 8.2 Hz, 4H), 5.71 (dq,J= 11.8,
1324, calcd 6.1 Hz, 1H), 4.05 (d, .1 : 9.8 Hz, 2H),
48 1224, calcd for 1.23 (d, J: 5.9 Hz, 3H), 1.13 (d, J: 6.7
1159, C18H30F3N02, Hz, 3H)
1137, 3201457;
1118, found, ”F NMR (376 MHz, CDC];) 5
1049, 7 -115.32,-115,70
1015, 955,
881, 826,
793, 779,
755, 746,
721, 693,
ESIMS
49 ——— ——— m z 341 ,5 ---
([M+Naj+)
ESIMS
m z 3 14,6
SO ___ ___ ___
“ (lM+HJ+)
ESIMS
777 Z 35644
51 ___ ___ ___
([M+H] )
ESIMS
m z 3024 19F NMR (376 MHz, CDCl3) 8
“52 ([M+H]+) -169.31
ESIMS
m z 344,;
i“) ___ ___ ___
‘ ‘ (lM+HJ )
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR
MASS NMR
N0. (‘0 (cm'l) (1H. 13C. 191:)
ESIMS
171 Z 3204
(| M+H r)
ESIMS
m z 352 .4
(lM+HJ+)
ESIMS
m Z 2824
([M—s—H]+)
ESIMS
m Z 2984
([M+H]+)
ESIMS
117 Z 442.4
(UVHHY)
ESIMS
m Z 324.4
([M—s—H]+)
ESIMS
mwz 312.3
([M+H]+)
ESIMS
172 Z 436
(| M+H |+)
ESIMS
m Z 3755
([M+Na]+)
ESIMS
64 m2 375 .5
([M+Na]+)
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR
MASS NMR
N0. (‘0 (cm'l) (1H. 13C. 191:)
ESIMS
171 Z 3445
(| M+H r)
ESIMS
m 2 344.5
(1M+HJ+)
ESIMS
177 Z 3485
([M+H]+)
ESIMS
m 2 38015
([M+H]+)
ESIMS
m 2 332.5
(1M+HJ+)
ESIMS
m Z 340.5
([M+H]+)
(Thin HRMS-ESI
?lm) (m z)
2959, ( 1M+H1+)
1749. cralcd
71 1508, calcd for
1401, F2N02,
1229. 306. 1300;
1 159. found.
1055, 830 306.1298
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. 13C. 191:)
(Thin
31:12) SI
’ 7. _‘ (m z)
2833.
1742/ ([M+H]+)
16013 calcd
72 ——— 1506 calcd for ---
‘
1454~ ,,
C19H22FZNOZ;
12'20’ 335.1646;
found.
1 ”9’5
‘ 335 1646
1136; '
1046, 824
($111? HRMS-ESI
(”7 Z)
2966 1
1736, ([M+H] )
1602, ”led
73 ——— ”07‘ calcd for ---
1&121> C20H24F2N02:
1158, 349.1803;
found.
1 1720‘
1046 8‘25 3491804
HRMS—ESI
(/77 Z)
2959.
173 9/
16033 calcd
74 ——— calcd for ---
1; 077‘
1219‘ C21H26F2N02>
11583 363.1959;
found.
1046" 212%1 122’ 363.1959
(Thin
3'1]? HRMS—ESI
7 ‘ (m 2)
([MH]+)
1740’
1605, calcd
75 ——— ”079‘ calcd for ---
1:153) C18H21FNOZ:
122,; 302.1551;
found.
1 1377
‘ 302 15513
1116, '
1049. 700
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd MP IR
NLASS NMR
140. (‘0 (cnfb (1H. 13C. 191:)
(11mm
33 3.
2941,
1743,
1467.
1385. E51848
1236, 0
1201. ([1V14—11]+)
1173.
1136,
1117,
1061.
1029,992.
824,755,
723,675
3361,
2942.
1742.
1582, ESIBIS
78 1486. n724040
1419. (I M 1')
1240,
1207,
1141.
1116.
1057,800
(T1?n
3218, f?thS-ESI
2980, (n72)
2945. ([84+TJTU
1742. cmcd
79 1522, calcd.?3r
1481. C20H24C12N02,
1245. 3801179;
1216, fbund,
1136, 3801181
1118.
1048. 758
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. 13C. 191:)
ESIMS
m 2 404.4
(| M+Hr)
ESIMS
m 2 336.5
<1M+HJ+>
ESIMS
m 2 408,5
([M+H]+)
(Thin
2881.
2193.
2130, 1H NMR (300 MHz, ol-d4) o 7.46,, -
1609, HRMS—ESI 7 7.30 (m, 2H). 7.28 7 7.14 (m, 4H). 5.84
1516‘ (m z) (dq, J: 10.1, 6.2 Hz. 1H), 4.24 (d. J:
1&57’ ([M+H]+) 10.1 Hz, 1H), 3.96 (q, J: 7.3 Hz, 1H),
14343 cralcd 3.31 (pd, J: 1.6, 0.5 Hz, 3H), 1.27 (d,J
84 : 6.1 Hz. 3H).
—-— 13%;“; calcd for 1.02 (d. .1: 7.2 Hz. 3H)
1532555 C18H18F4N02,
12853 356.1268; F NMR (471 1\/H-Iz,methanol-d4) o -a
1208 found, 139.39 (ddd. .1: 19.8, 11.5. 7.5 Hz),
1118‘ 3561273 - 39.57 7 -139.84 (m). -142.33 7
-142.56 (111), -142.66 — -142.93 (In)
1049 966
906, 875.
821, 754,
710, 692,
681, 656
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, 13C, 191:)
(Thin
3409,
2928,
2026, 1H NMR (300 MHz, methanol-d4) 5 7.54
1957,
, (dt, J: 7.0, 2.7 Hz, 2H), 7.37 (ddt, .1:
HRMS‘ESI
1743, 8.6, 4.3, 2.1 Hz, 2H), 7.21 (td, J: 8.8,
1597, “Sign 4.7 Hz, 2H), 5.93 — 5.75 (m, 1H), 4.24 (d,
1499, J: 10.1 Hz, 1H), 3.96 (q, J: 7.3 Hz,
cr'11cd
1458,
1H), 3.31 (t, J: 1.7 Hz, 3H), 1.28 (d, .1:
___ cal‘cd for
Egg, 6.1 Hz, 3H), 1.03 (d, J7 7.3 Hz, 3H)
C18H18C13F2N02,
’ 388.0677;
1249‘,.
found 1‘
1208, )F NMR (471 MHz, methanol-d4) 5
388 0677
1118, ' -119.62—-119.72(m), -119.99—
1061, 917, -120.08 (111)
866, 822,
798, 780,
753, 718,
690, 663
(Thin
3374,
2928,
1742,
1596, 1H NMR (300 MHz, methanol-d4) 5 7.30
1501, HRMS-ESI 7 7.12 (m, 4H), 6.95 (td, .1: 8.9, 6.6 Hz,
1457, (m 2) 2H), 5.91 7 5.74 (m, 1H), 4.07 (d, .1:
1379, +) 104 Hz, 1H), 3.99 — 3.83 (1n, 1H), 330
1323, calcd (dtd, J: 3.3, 16, 0.6 Hz, 3H), 2.23 (t, J:
86 ——— 1233, calcd for 2.6 Hz, 6H), 1.25 (d, .1: 6.1 Hz. 3H),
1206, C30H24F3N02, 0‘94 (dd, J : 73, 0.7 Hz, 3H)
1118, 348.1770;
1052, found, 19F NMR (471 MHZ, methanol-d4) 5
1003, 956, 348.1771 -122.0() 7 -122.37 (In), -122.69 (11.1:
933, 886, 6.1, 2.9 Hz)
824, 780,
752, 721,
711, 690,
681, 671,
664, 655
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, 13C. 19F)
(Thin
2879,
1746,
1587,
(”7 Z)
‘ +
(| M+H| )
1317,_
calcd
87 --- 1395’ calcd for ---
1227’ CIXHIXChNOg,
‘ 6;
1194,,,
found,
_,,’ 4200090
1033,
1029, 871.
822, 747,
727, 669
(Thin
2858,
1747,
1580, HRMS-ESI
1486, (m z)
145 8, ([M+H]+)
1383, calcd
88 ——— 1368, calcd for ---
1278, C18H18C13F3N03,
1236, 3880677;
1206, found,
1119, 388.0688
1048, 970,
871, 824,
779, 761,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. ”C. 191:)
1H NMR (500 MHz, CDC13) 8 11.97 (d, J
= 0.5 Hz, 1H). 8.33 (d, J: 8.1 Hz, 1H),
7.96 (d. J: 5.2 Hz. 1H). 7.47 (ddt. J:
HRMS-ESI 8.5. 6.4. 1.3 Hz. 4H), 7.33 4 7.13 (m.
(m 2) 5H), 6.89 4 6.81 (m. 1H). 6.03 (q, J: 6.3
[MT Hz. 1H). 4.62 4 4.49 (m. 1H). 3.93 (s.
calcd for 3H). 2.74 (s. 1H). 1.23 (d. J : 6.3 Hz.
Cstz?Nzoé, 3H), 1.07 (d. J: 7.2 Hz. 3H)
450.1791;
found. ”C NMR (126 MHz. CD(‘,1~.)8 171.30.
450.1794 168.61.155.37.148.71.144.85, 142.71,
140.44.130.29,128.33, 128.32. 127.22,
127.16.125.51.125.45. 109.44. 79.57.
75.54. 56.08. 47.85. 17.62. 14.32
1H NMR (400 MHz, CDC13) 8 12.10 (d, J
= 0.6 Hz, 1H). 8.34 (d, J: 8.0 Hz, 1H),
7.98 (d. J: 5.2 Hz. 1H). 7.38 4 7.06 (m.
“mi-ES] 1011). 6.86 (dd. J: 5.3. 0.7 Hz. 1H). 583
(dq,J= 10.1. 6.1 Hz, 1H). 4.52 (dq. J:
([M+H]+)
8.1. 7.2 Hz. 1H). 4.06 (d. .1: 10.2 Hz.
1H). 3.93 (s. 3H). 1.26 (d. J: 6.1 Hz.
90 “?ed for
3H) 0 97 (d J: 7 2 Hz 3H)
C25H2‘N205, 3 5 " 5 "
11961202 ”C NMR (101 MHz. CD(‘,1~.)8 171.67.
43; 192*; 168.53.155.3414872,141,38, ,
*' “ 140.40.130.48,128.80, 128.50. 128.10,
128.03. 126.95. 126.70. 109.39. 73.57.
57.93. 56.07. 47.85. 19.24. 17.61
1H NMR (400 MHz, CDC13) 8 12.10 (d, J
= 0.6 Hz, 1H). 8.41 (d, J: 8.0 Hz, 1H),
7.98 (d. J: 5.2 Hz. 1H). 7.18 4 7.16 (m.
“mi-ES] 2H). 7.01 (ddd. J: 3.6, 1.3. 0.6 Hz. 1H).
6.94 4 6.88 (m, 3H). 6.86 (dd. J: 5.3. 0.7
([M+H]+)
Hz. 1H). 5.56 (dq. J: 7.4. 6.2 Hz. 1H).
calcd
4.70 4 4,58 (m. 2H). 3.94 (s. 3H). 1.30 (d.
91 calcd for
J4 6.2 Hz, 3H), 1.24 (d. J4 7.2 Hz. 3H)
C21H23N20582,
4:233:8‘ ”C NMR_(_101_ MHz. CDCE.) 8 171.48.
168.62.155.33.148.74, , 142.69,
447.1047
140.43. 130.48, 126.77, 126.57, 126.05,
125.43. . 124.58. 109.44. 74.83.
56.08. 47.98. 47.42. 18.69. 17.80
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDClg) 5 12.06 (d, J
HRMS—ESI = 0.7 Hz, 1H), 8.32 (d, J: 8.0 Hz, 1H),
(m z) 7.98 (d. J: 5.3 Hz. 1H). 7.26 4 7.18 (m.
([M+HJ+) 4H), 7.01 4 6.89 (m, 4H), 6.87 (d, J: 5.3
calcd Hz, 1H), 5.73 (dq, J: 9.7, 6.1 Hz, 1H),
92 ——— ——— calcd for 4.59 2 4.49 (m. 11-1). 405 (d. J: 9.8 Hz.
CZSHEFZNZOS. 1H). 3.94 (s. 3H). 1.25 (d. J: 6.2 Hz.
471.1731; 3H), 1.07 (d,J= 7.2 Hz, 3H)
found,
471.1735 ”F NMR (376 MHz. ~,)5
6, —115.80
1H NMR (400 MHz, CDClg) 5 12.03 (d, J
: 0.7 Hz. 1H). 8.40 (d. .1: 8.1Hz. 1H).
7.97 (d. J: 5.2 Hz. 1H). 7.41 4 7.09 (m.
10H), 6.85 (d,J= 5.2 Hz, 1H), 5.97 (q, J
HRMS—ESI = 6.3 Hz, 1H), 4.61 (dq, J: 8.2, 7.2 Hz,
(/77 z) 1H). 3.94 (s. 3H). 3.39 (dq. J: 9.1. 6.9
[2M+Nar Hz, 1H), 3.18 (dq,J: 9.2, 6.9 Hz, 1H),
calcd for 1.30 (d, J: 7.2 Hz, 3H), 1.17 (t, J: 6.9
C54HMN4NaOIZ. Hz. 3H). 1.13 (d. J: 6.3 Hz. 3H)
979.4106;
found, 13C NMR (101 MHz, CDC13) 5 171.45,
979.4119 168.56,155.34,148.71, 141.84, 140.56,
. . 128.25. 127.87. 127.81.
127.69,127.33,127.21, 109.41, 84.05,
74.30, 59.93, 56.08, 48.05, 18.02, 15.67,
14.95
1H NMR (300 MHz. CDCL.) 5 1204 (d. J
= 0.6 Hz, 1H), 8.41 (d, J: 8.0 Hz, 1H),
7.97 (d,J= 5.2 Hz, 1H),7.41— 7.18 (m,
HRMS'ESI,
10H). 6.85 (d. J: 5.4 Hz. 1H). 5.97 (q. J
[MfgCZHr : 6.3 Hz, 1H), 4.75 4 4.49 (m, 1H), 3.94
(3, 3H), 3.15 (s, 3H), 1.29 (d, J: 7.2 Hz,
calcd f0}
95 3H). 1.13 (d. .1: 6.3 Hz. 3H)
4311761
13C NMR (101 MHz, CDC13) 5 171.42,
found,
168.58,155.35,148.72,141.11.140.39,
433.1763
139.89. 130.37. 128.51. 128.11. 127.86.
127.69. 127.52, 127.31, 109.42, 84.47,
74.02, 56.08, 52.55, 48.05, 17.97, 14.97
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NIVIR
N0. (‘0 (cm'l) (1H, 13C. 191:)
1H NMR (400 MHz, CD03) 5 12.03 (d, J
= 0.6 Hz, 1H), 8.31 (d, J: 7.9 Hz, 1H),
7.97 (d, .1: 5.2 Hz, 1H), 7.35 (td, .1: 8.5,
6.2 Hz, 1H), 7,23 (td, J : 8.4, 6.2 Hz,
1H), 6.91 4 6.74 (m, 4H), 6.69 (ddd, J:
.4, 8.8, 2.6 Hz, 1H), 5.88 4 5.74 (m,
1H), 4.69 (d, .1: 9.9 Hz, 1H), 4.64 4 4.48
(m, 1H), 3.95 (s, 3H), 1.30 (d,J= 6.1 Hz,
3H), 1.17 (d,J= 7.2 Hz, 3H)
”P NMR (376 MHz, CDC13)8
-110.97 (d,J= 7.7 Hz), -111.39 (d, J:
76 Hz), 41 1 1.98 (dd, .1: 7.7, 2.6 Hz), 4
112.83 (dd, .1: 7.6, 2.6 Hz)
1H NMR (400 MHz, CDC13) 5 12.06 (s,
1H), 8.31 (d,J= 7.9 Hz, 1H), 7.98 (61.1:
.2 Hz, 1H), 7.49 4 7.40 (m, 4H), 7.37 4
7,24 (m, 5H), 7,23 4 7.18 (m, 1H), 6.86
(d, J: 5.2 Hz, 1H), 6.00 (dq, J: 25.4,
97 6.4 Hz, 1H), 4.63 4 4,51 (m, 1H), 3.94 (s,
3H), 1.32 (dd, .1: 6,5, 1.0 Hz, 3H), 0.96
(d, J: 7.2 Hz, 3H)
”P NMR (376 MHz, CD(‘,1~,) 5
-169.17
1H NMR (400 MHz, CDClg) 5 12.11 (s,
1H), 8.35 (d, .1: 8.0 Hz, 1H), 7.97 (d, .1:
.2 Hz, 1H), 7.22 4 7.12 (m, 4H), 6.90 4
HRMS—ESI 6.73 (m, 5H), 5.73 (dq, J: 9.8, 6.1 Hz,
(m z) 1H), 4.64 4 4,44 (m, 1H), 3.96 (d, J: 9.9
(| M+H F) Hz, 1H), 3.93 (s, 3H), 3.75 (s, 3H), 3.73
calcd (5,311), 1.24 (d, .1 : 6.2 Hz, 3H), 1.05 (d,
98 calcd for J: 7.2 Hz, 3H)
N2074
495 .2 13 l ; ”C NMR (101 MHz, CDCL.) 5 171.65,
found, 168.54,158.36,158.20,155.34,148.70,
24 140.40,133.83,133.69, 130.45, 128.97,
128.92, 11411, 113.81, 109.39, 7377,
5611, 56.04, 55.20, 55.19, 47.90, 1920,
17.75
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13)8 12.05 (s,
SI 1H), 8.34 (d, J: 8.0 Hz, 1H), 7.98 (d, J:
(m z) 5.3 Hz, 1H), 7.32 4 7.19 (m, 2H). 7.1 1 4
([M4Hr) 703 (111,211), 7.02 4 6.83 (m, 5H), 5,75
calcd (dq,J= 9.8, 6.1 Hz, 1H), 4.65 4 4.46 (m,
99 calcd for 1H), 4.06 (d, .1: 9.9 Hz, 1H), 3.94 (s,
CZSHEFZNZOS, 3H), 1.27 (d, .1: 6.1 Hz, 3H), 1,07 (d, .1:
471.1731; 7.2Hz, 3H)
found,
4711724 ”F NMR (376 MHz. CD(‘,1~,) 5
7, -112.48
1H NMR (400 MHz, CDClg) 5 12.04 (s,
1H), 8.32 (d, .1: 7.7 Hz, 1H), 7‘98 (01, .1:
.3 Hz, 1H). 7.31 4 7.10 (m, 8H), 6.86 (d,
HRxSZfSI J: 5.2 Hz, 1H), 5.73 (dq, J: 9.9, 6.2 Hz,
1H), 4.60 4 4.48011, 1H), 4.01 (d, J:
([NHHT)
.0 Hz; 1H), 3.94 (s. 3H), 1.27
calcd (51, .1:
6.2 Hz, 3H), 1.08 (d, J4 7.1 Hz, 3H)
100 calcd for
C$3€11E)0 13C NMR (101 MHz. CDC1,)5 17155,
‘ found ‘ 168.60, 155,36, 14872. 142.54, 142.33,
140.47, 134.73, 134.42, 130.33, 130.23,
503 1137'
129.94,128.42,128.33, 127.52, 127.21,
126.18, 125.98, 109.47, 72.83, 57.03,
56.08, 47.85, 1911,1766
HRMS—ESI 1H NMR (400 MHz, CDClg) 5 12.23 4
(m z) 11.94 (m. 1H), 8.64 4 8.39 (m. 1H), 8.11
(119141115 4 7.92 (m. 1H), 7.78 4 7.60 (m, 3H), 7.59
calcd 4 7.48 (m, 1H), 7.46 4 7.35 (m, 2H), 7.36
101 calcd for — 7.26 (m, 1H), 7.27 4 7,20 (m, 1H), 6.91
(725113514205, 4 6.84 (m. 1H), 5.87 4 5.69 (m, 1H), 4.94
433.1763; 4 4.76011, 1H), 4.35 4 4,22 (m, 1H), 400
found, — 3.93 (m, 3H), 1.69 — 1.51 (m, 3H), 0.95
4331749 4 0.59 (m. 3H)
HRMS-ESI
(m z) 1H NMR (400 MHz, CDC13) 5 12.16 (s,
([M+H]+) 1H),8.514 8.38011, 11— 7.82 (m,
calcd 1H), 7.34 4 7.15 (m. 4H), 7.15 4 6.94 (m,
102 ——— ——— calcd for 4H), 6.91 2 6177 (m, 1H), 5120 2 5.09 (m,
C25H35N306, 1H), 4.78 4 4.64011, 1H), 4.33 4 4.17 (m,
449.1712; 1H), 3.96 4 9.92 (m, 3H), 1.55 4 1.42 (m,
found, 3H), 1.104091 (m. 311)
449.1707
[Annotation] an
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. ”C. 191:)
1H NMR (400 MHz, CDC13) 5 12.06 (s,
1H), 8.33 (d,J= 7.9 Hz, 1H), 7.97 (d,J=
.2 Hz. 1H). 7.50 4 7.31 (m. 4H). 7.24 4
“113717551381 7.01 (m, 4H), 6.87 (d, J: 5.2 Hz, 1H),
.73 (dq, J: 9.6, 6.1 Hz, 1H), 4.55 (p,J
([M+H]+)
: 7.3 Hz. 1H). 4.01 (d. .1: 9.7 Hz. 1H).
calcd
3.93 (s. 3H). 1.25 (d;./: 6.1 Hz. 3H).
103 calcd for
1.09 (d, J— 7.2 Hz, 3H)
CstszerzOs,
5910130; 12, (, NMR_(_101 MHz. CD(,1~,) 5 171.50.4 4 4 4 _
found
168.61.155.3914874,140.47, 139.69,
591 012‘;' “ 139.59,132.00,131.69, 130.31, 129.80,
129.73.121.12.120.84. 109.52.72.81.
56.45. 56.08. 47.86. 19.09. 17.67
1H NMR (400 MHz, CDC13) 5 12.13 (s,
1H), 8.44 (d,J= 8.0 Hz, 1H), 7.99 (d,J=
.2 Hz. 1H). 6.87 (d. .1: 5.2 Hz. 1H).
HRMS-ESI 6.73 (d, J: 3.4 Hz, 1H), 6.67 (d, J: 3.4
(m z) Hz, 1H), 6.54 4 6.35 (m, 2H), 5.54 4 5.40
(1M4Hr) (m. 1H). 4.78 4 4.59 (m. 1H). 4.45 (d. .7:
calcd 7.1 Hz. 1H). 3.94 (s. 3H). 2.39 (s. 6H).
104 calcd for 1.30 (d, J: 2.8 Hz, 3H), 1.28 (d, J: 3.7
C33H3-Ngossg, Hz, 3H)
475.1361;
found, ”C NMR (101 MHz, CDC13) 5 171.50,
475.1368 168.60,155.35,148.74, 141.52, 140.47,
140.41. 139.03. 139.00. . 125.76.
125.08. . 124.42. 109.41. 74.68.
5607,4800, 47.84, 18.65, 17.88, 15.25
1H NMR (400 MHz, CDC13) 5 12.14 (s,
1H). 8.38 (d. .1: 8.0 Hz. 1H). 7.94 (d. .1:
.2 Hz, 1H),7.214 7.10 (m, 4H), 7.09 4
6.97 (m, 4H), 6.82 (d, J: 5.2 Hz, 1H),
HRSiSZfSI, 5.79 (dq. .1: 10.1. 6.2 Hz. 1H). 4.53 (p. .7
: 7.3 Hz. 1H). 3.98 (d. .1: 10.0 Hz. 1H).
(1MMy)
3.88 (s, 3H), 2.25 (s, 3H), 2.23 (s, 3H),
calcd
_ 1.25 (d, J: 6.3 Hz, 3H), 1.01 (d, J: 7.2
105 ——— ——— calcd for
Hz 3H)
C27HEINZOS~ ‘ 5
42312131 ”C NMR (101 MHz, CDC13) 5 171.66,
168.57. 155.32. 148.71. 140.43. 138.63.
463.2242
. 136,37. 136.05. 130.45. 129.44.
129.11,127.91,127.85, 109.45, 73.66,
57.08. 56.02, 47.92, 20.97, 20.93, 19.24,
17.64
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. ()0 (cm'l) (H, ”C, 191:)
1H NMR (400 MHz, CDClg) 5 12.09 (s,
, 1H), 8.35 (d,J= 8.0 Hz, 1H), 7.97 (01.1:
HRR’IS'ESI
.2 Hz, 1H), 7.54 (d, .1: 8.1 Hz, 2H),
([?ig? 7,42 (d, J: 8.1 Hz, 2H), 7.34 4 7.21 (m,
4H), 7.21 4 7.13 (m, 1H), 6.86 (d, J: 5.2
calcd
Hz, 1H), 5.85 (dq, .1: 9,8, 6.1 Hz, 1H),
106 calcd for
4.614 4,46 (m, 1H), 4. 15 (d, .1 : 9.9 Hz,
C) H) F~N7O-
50361794 1H), 3.93 (s, 3H), 1.27 (5,11: 6.2 Hz,
3H), 1.00 (d, J— 7.2 Hz, 3H)
found
3011794
”P NMR (376 MHz, CDC13)8
-62.53
1H NMR (400 MHz, CDC1~,) 5 12.05 (s,
1H), 8.32 (d, .1: 8.0 Hz, 1H), 7,97 (d, .1:
HRMS—ESI 5.2 Hz, 1H), 7.38 4 7.10 (m, 8H), 6.87 (d,
(777 z) J: 5.2 Hz, 1H), 5.73 (dq, J: 9.9, 6.2 Hz,
(| M+H|+) 1H), 4.62 4 4.45 (m, 1H), 4.03 (d, .1: 9.6
calcd Hz, 1H), 3.94 (s, 3H), 1.25 (d, J: 6.1 Hz,
107 calcd for 3H), 1.09 (d, J: 7.2 Hz, 3H)
C25H25C12N2054
503.1140; ”C NMR (101 MHz, CD07.) 5 171.52,
found, ,155.41,148.74, 140.45, 139.26,
503.1139 139.15,133.04,132.77,1303212941,
129.36, , 128.73, , 7295,
5635, 56.08, 47.86, 19.08, 17.67
1H NMR (400 MHz, CDClg) 5 12.10 (s,
1H), 8.36 (d, .1: 7.9 Hz, 1H), 7.95 (d, .1:
.2 Hz, 1H), 7.57 4 7.46 (m, 8H), 7.43 4
7.38 (m, 7H), 7.34 4 7.29 (m, 2H), 6,81
(d,J= 5.2 Hz, 1H), 5.90 (dq,J= 12.2,
6.1 Hz, 1H), 4.56 (p, .1: 7.2 Hz, 1H),
4.16 (d, J: 100 Hz, 1H), 3.89 (d, J: 1.9
ESIMS
Hz, 3H), 1.34 (51,]: 6.1 Hz, 3H), 1.02
W Z 587
109 (d, .1: 7.2 Hz, 5H)
(I M+H|+)
13C NMR (101 MHz, CDC13) 5 171.71,
168.59,155.33,148.72, 140.65, 140.58,
140.43, 140.11, , 139.66, 130.44,
128.77,128,73,128.67, 128.53, 127.58,
127.30,127.26,127.21, 127.00, 126.94,
109.40, 73.58, 57.25, 5604, 47.91, 19.33,
17.66
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
(Thin
3374,
2984, 1H NMR (400 MHz, CDC13)8 11.80 (s,
1735, 1H), 8.30 (d,J= 8.0 Hz, 1H), 8.07 (dd,J
1649, : 4.3, 1.5 Hz, 1H), 7.40 4 7.15 (m, 6H),
1602, 7.05 4 6,85 (111,4H), 5.73 (dq, .1: 9.8, 6.2
1577, Hz, 1H), 4.65 — 4.45 (m, 1H), 4.05 (d, J:
1530, HRMS—ESI 9.8 Hz, 1H), 1.25 (d, J: 6.1 Hz, 3H),
1507, (m z) 1.07 (d, .1: 7.2 Hz, 3H)
1449, (1M4Hr)
1380, calcd ”C NMR (101 MHz, CDC13) 5 171.60,
1 10 1329, calcd for 168.26, 16 1 .76 (d, .1: 246.1 Hz), 161.64
1296, (734H13F3N304, (d, .1: 2457 Hz), 157.79, 139.65, 136.82
1222, 441.1620; (d,J= 3.3 Hz), 136.71 (d,J= 3.5 Hz),
1188, found, 13104, 129.50 (d,J= 7.9 Hz), 128.80,
1159, 4411620 , 115,74(d,.1: 21.3 Hz), 115.41
1130, (d,J: 21.3 Hz), 7334, 56.14, 47.84,
1105, 19.12, 17.69
1049,
1015, 906, ”P NMR (376 MHz, CD(‘,1¢.)5
826, 809, -115.44, -11576
792, 778,
731, 704,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
(Thin
3370, ‘HNMR (400 MHz, CD(‘,1~,)5 1206 (d, J
2984, : 06 Hz, 1H), 8.33 (d, J: 8.0 Hz, 1H),
2936, 7.95 (d, J: 5.2 Hz, 1H), 7.35 — 7.14 (m,
2256, 4H), 7.04 4 6,87 (m, 4H), 6.84 (d, .1: 5.2
1735, Hz, 1H), 5.73 (dq,.1: 9.7, 6.1 Hz, 1H),
1647, 8 (m, 1H), 4.16 (q,J= 7.0 Hz,
1604,
“Eff“,
2H), 4.05 (d, J: 9.7 Hz, 1H), 1.51 (t, J:
1574, 7.0 Hz, 3H), 1.24 (d, .1: 6.1 Hz, 3H),
1:32 1,06 (d, J 72 Hz, 3H)
([M+H]+)
1483,
1 11 0,333?“ 13C NMR (101 MHz, 5 171,58,
1469, 168.66, 161.75(d,.1: 2461 Hz), 161.64
C7 H7—F7N70-
1452, ‘28; 1883- (d,J= 2457 Hz), 154.75, 148.82,
1381, 16mm = 140.38,136.82(d,J= 3.3 Hz), 13673 (d,
1323, .1: 3.3 Hz), 130.41, 12951 (d, .1: 7.6
48, 1m)
1281, 5' Hz), 115.72(d,J:21.411z), 115.39(d,J
1262, = 21.2 Hz), 110.13, 467, 5612,
1222, 4784,1911, 1769,1437
1 158,
1109, ”F NMR (376 MHz, CDC13) 8
1048, -115.47, -115.80
1015, 990,
904, 824,
800, 730
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
(Thin
3370,
2984, 1H NMR (400 MHz, CDC13)8 12.05 (s,
1729, 1H), 7.43 — 7.33 (m, 2H), 7.30 — 7.17 (m,
1641, 4H), 7.05 4 6,90 (m, 5H), 6.88 4 6,77 (m,
1601, 2H), 5.75 (dq, .1: 9,9, 6.1 Hz, 1H), 4.57
1531, (p,J=7.l Hz, 1H),4.06(d,J=9.9 Hz,
1507, HRMS—ESI 1H), 1.25 (d, J: 6.1 Hz, 3H), 1.00 (d, J:
1491, (m z) 7.1 Hz, 3H)
1450, (1M4Hr)
1361, calcd ”C NMR (101 MHz, CDC13) 5 172.22,
112 1305, calcd for , 16 1 .79 (d, .1: 246.2 Hz), 161.70
1281, CZSHNFJNOd, (d, .1: 2459 Hz), 161.59, 136.83 (d, .1:
1254, 440.1668; 3.4 Hz), 136.61 (d,J= 3.4 Hz), 134.49,
1222, found, 12949 (d, J: 8.1 Hz), 12946 (d, J: 7.9
1177, 4401676 Hz), 125.62, 118.70, 118.58, 11579 (d, .1
1158, :21.4Hz), 115.50 (d,J:21,3 Hz),
1135, 113.72, 73.62, 56.17, 48.29, 19.15, 17.79
1087,
1048, ”P NMR (376 MHz, C190,) 5
08, -115.30,-115.60
824, 778,
752, 731,
1H NMR (400 MHz, CDClg) 5 11.98 (d, J
: 0.6 Hz, 1H), 8.30 (t, .1: 5.7 Hz, 1H),
7.99 (d, .1 : 5.2 Hz, 1H), 7.24 4 7.15 (m,
4H), 7.03 — 6,85 (m, 5H), 5.71 (dq, J:
9.2, 6.2 Hz, 1H), 4.11 (dd,J= 18.1, 6.0
Hz, 1H), 4.04 (d, .1: 9.2 Hz, 1H), 3.95 (s,
ESIMS 3H), 3.90 (dd, J: 18.1, 5.6 Hz, 1H), 1,25
m/Z 457.6 (d, J: 6.3 Hz, 3H)
(HWHT)
”C NMR (101 MHz, CDCI3) 5 169.18,
168.43,161.74(d,J= 246.1 Hz), 161.63
(d,J=245.5 Hz), 155.42, 148.71,
140.55, 136.68, 130.30, 129.68, ,
115.67 (d,J: 29.2 Hz), 115.46 (d,J:
29.1 Hz), 109.55, 73.65, 56.11, 55.77,
40.91, 19.12
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NIVIR
N0. (‘0 (cm'l) (1H, 13C. 191:)
1H NMR (400 MHz, CDC13) 5 12.08 (s,
1H), 8.32 (d,J= 8.5 Hz, 1H), 7.98 (61.1:
.2 Hz, 1H), 7.46 4 7.04 (m, 4H), 7.1 1 4
6.65 (m, 5H), 5.71 (dq, J : 9.8, 6.2 Hz,
1H), 4.51 (ddd,J= 8.5, 7.0, 5.4 Hz, 1H),
4.05 (d, .1: 9.6 Hz, 1H), 3.95 (s, 3H),
1.704 1,57 (m, 1H), 1.49 4 1.36 (m, 1H),
ESIMS 1.24 (d, J: 6.2 Hz, 3H), 0.67 (t, J: 7.5
m 2 485.6 Hz, 3H)
(| M+H |+)
”C NMR (101 MHz, CDC13) 5 170.87,
168.79,161.74(d,J= 245.9 Hz), 161.66
(d, .]:245.8 Hz), , 148.73,
140.42, 136,80, 13036, 129.55 (d, .1:
2.7 Hz), 129.47 (d, J: 2.7 Hz), 115.67
(d, J: 32.4 Hz), 115.45 (d, J: 32.4 Hz),
109.44, 73.48, 56.09, 56.03, 53.16, 25.16,
19.18, 9.27
1H NMR (400 MHz, CDClg) 5 12.08 (d, J
: 0.6 Hz, 1H), 8.32 (d, .1: 9.4 Hz, 1H),
7.98 (d, .1: 5.2 Hz, 1H), 7.31 4 7.07 (m,
4H), 6.97 (t, J: 8.6 Hz, 2H), 6.93 — 6.86
(m, 3H), 5.72 (dq, J: 9.7, 6.2 Hz, 1H),
4.48 (dd, .1 : 9.4, 4.7 Hz, 1H), 4.05 (d, .1
: 9.7 Hz, 1H), 3.95 (s, 3H), 1.93 4 1,82
(m, 1H), 1.23 (d, J: 6.1 Hz, 3H), 0.82
ESIMS
(d, .1: 6.9 Hz, 3H), 0.65 (d, J: 6.8 Hz,
m 2 499.6
(UVHHY)
”C NMR (101 MHz, CDC13) 5 ,
168.95, 16173 (d, .1: 2464 Hz), 161.65
(d,J:245.6 Hz),155.43, 148.71,
140.42, 136.85, 130.40, 129.54 (d,J=
4.7 Hz), 12947 (d, .1: 4.7 Hz), 11571
(d, .1: 21.3 Hz), 11540 (d, .1: 21.3 Hz),
109.43, 73.51, 57.09, 56.09, 55.98, 30.96,
19.22,19.10,17.10
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 8 12.07 (d, J
= 0.6 Hz, 1H), 8.15 (d, J: 8.9 Hz, 1H),
7.97 (d. .1: 5.2 Hz. 1H). 7.31 4 7.04 (m.
4H), 7.08 4 6.74011, 6H), 5.70 (dq, J:
.0, 6.1 Hz, 1H), 4.54 (ddd, J: 9.7, 8.8,
.0 Hz. 1H). 4.04 (d. .1: 9.8 Hz. 1H).
3.94 (s. 3H). 1.46 4 1.36 (m. 1H). 1.33 4
1.18 (111,4H), 1.08 (ddd: J: 13.9, 9.0, 5.0
ESIMS
Hz, 1H), 0.82 (EU: 6.5 Hz, 3H), 0.77
m Z 5137
116 (d. .14 6.6 Hz. 3H)
(I WHF)
”C NMR (101 MHz, CDC13) 8 171.62,
168.81. 161.75 (d. .1:246.2 Hz). 161.66
(d..1:245.6 Hz). 155.43. 148.74.
140.39,137.02,136.76, 130.34, 12951
(d, J: 3.4 Hz), 129.44 (d, J: 3.5 Hz),
115.73 (d..]:21.4 Hz). 115.41 (61.1:
21.3 Hz), , 73.37, 56.21, 56.09,
50.52, 41.00, 24.57, 22.76, 21.49, 19.14
1H NMR (300 MHz.CDC1~.)5 1215 (d. J
(Thin : 0.6 Hz. 1H). 8.38 (d. .1: 8.0 Hz. 1H).
?lm) 7.97 (d, J: 5.2 Hz, 1H), 7.45 (dd, J:
3368, (“$313 7.6, 1.7 Hz, 1H), 7.30 4 7.20 (m, 1H),
2937. 7.12 (dddd..1: 13.5. 8.1. 7.5. 1.7 Hz.
calcd for
117 1732, 2H), 6.92 4 6.80 (m, 4H), 6.76 (dd,J:
C H N 0
1648, $953136?) 8.2, 1.1 Hz, 1H), 5.97 (dq,J= 9.0, 5.7,
1527. {6111161 ‘ 5.2 Hz. 1H). 5.01 (61.1: 10.1 Hz. 1H).
1241. 4.70 4 4,39 (m. 1H). 3.93 (s. 3H). 3.85 (s.
49, 2164
1144 " 3H), 3.75 (s, 3H), 1.25 (d, J: 6.2 Hz,
3H), 1.01 (d, J: 7.2 Hz, 3H)
:W1(iii?2““25‘301’S1hi'11‘ii?"z. .35 :
£13122 HR?SZ'ESI . . . . . .
7.98 (d, J: 5.2 Hz, 1H), 7.21 (t, J: 8.0
2937’ Hz. 1H). 7.15 (LJ: 7.9 Hz. 1H).6_934
(1M+H|+)
1773 4‘ 6.81 (m. 5H). 6.74 (ddd../: 8.2. 2.6. 0.9
calcd
118 1648’ Hz, 1H), 6.68 (ddd,J= 8.2, 2.6, 0.9 Hz,
C77H~ N707
”27’ 419;;12‘6‘ = 1H), 5.80 (dq,J= 10.3, 6.1 Hz, 1H), 4.60
1‘26 1‘ 156111161 ‘
4 4.43 (m. 1H). 3.99 (d. .1: 10.3 Hz. 1H).
3.94 (s, 3H), 3.77 (s, 3H), 3.75 (s, 3H),
1 148‘ 49, 2106
1041’ " 1.26 (d,J= 6.0 Hz, 3H), 1.00 (d,J= 7.2
Hz. 3H)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
(Thin
?lm) 1HNMR (300 MHz, CDClg) 5 11.92 (s,
HRMS'ESI,
3367, 1H), 8.36 (d, .1: 8.1 Hz, 1H), 7.95 (d, .1:
2985, “Sign 52 Hz, 1H), 777 (t, J: 8.5 Hz, 1H),
1738, 7.37 (t, J: 8.5 Hz, 1H), 7.15 (ddd, J:
Galed for
119 1647, 8,5, 2.1, 07 Hz, 1H), 70846.89 (m,
(,rHerRMO
1575, 5‘55 0896; "* 3H), 6.86 (5,.1: 5.3 Hz, 1H), 6.10 (q, .1:
1481, “ 151111 * 62 Hz, 1H), 4.66 (p, J: 7.3 Hz, 1H),
1263, 3.95 (s, 3H), 3.22 (s, 1H), 1.36 (d,J= 7.2
555 0909
1153, “7' Hz, 3H), 1.24 (d, .1: 6.3 Hz, 3H)
1058, 914
($111; 1H NMR (300 MHz, CDClg) 5 12.06 (d, J
: 0.6 Hz, 1H), 8.34 (d. .1: 8.0 Hz. 1H),
3369 (m Z)
‘2‘934‘ 7,98 (d, J: 52 Hz, 1H), 7.16 4 7.01 (m,
([M+H]+)
173; 2H), 7.01 4 6.79 (m, 5H), 5.70 (dq, J:
031Cd for
120 1648’ 99,61 Hz, 1H), 4.70 4 4.43 (m, 1H),
(,7 H71 RN70
1576* [4992039 3.97 (d, .1: 9.3 Hz, 1H), 3.94 (s, 3H),
1ng fo11nd * 2.20 (d,J= 19 Hz, 3H), 2.17 (d, J: 1.9
i- ’ :
, Hz,3H), 1.25 (d,J= 6.1 Hz, 3H), 1.09
1451, 4992050
(d 1:?2HZ 3H)
1261 *' ‘ “
mm 1H NMR (300 MHz CDClg) 5 12 14 4
£1112? HR?’IS')ESI 1 1.95 (m, 1H), 8.33 (d, .1: 8.0 Hz, 1H),
2980‘ (MEN) 7.98 (d, .1 : 5.2 Hz, 1H), 7.21 (d. .1: 1.5
1735’ Hz, 2H), 7.19 4 6.99 (m, 4H), 6.86 (d, J:
calcd for
121 1648= 5.2 Hz, 1H), 5.69 (dq, J: 9.8, 6.1 Hz,
C7 H71C17N70-
”27* 533,1) 1448 1H), 4.55 (p,./: 7.3 Hz, 1H), 3.94 (51,7:
1450* ”fo'und * 99 Hz, 1H), 3,94 (s, 3H), 2.31 (s, 3H),
1262= 531 14328 2.27 (s, 3H), 1.25 (d, J: 6.0 Hz, 3H),
' ' ' 1,10(d,.]:7,2Hz,3H)
1H NMR (300 MHZ, CDC13)8 12.00 (d, J
(Thin
= 0.6 Hz, 1H), 8.41 (d, J: 8.1 Hz, 1H),
7,97 (d, .1: 5.2 Hz, 1H), 7.87 4 7,75 (m,
3,67 HRMSESI
3986* 1H), 7.48 (11.1: 8.0. 1.5 Hz, 1H). 7.28 4
(W Z)
1737’ 7.12 (m, 3H), 7.10 4 6.98 (m, 1H), 6.99 4
([M+H]+)
164; 6.86 (m, 2H), 6.90 4 6.82 (m, 1H), 6.26
calcd for
122 1611* (qd, .1: 6.3, 1.5 Hz, 1H), 4.73 4 4.57 (m,
_F7N7O
1482* [187:107? "* 1H), 3.94 (s, 3H), 3.19 (dd,J: 2.8, 1,9
= ' ” Hz, 1H), 1.28 (d,J= 6.3 Hz,3H), 1.27
1432,_, found,
(d I: 7 2 Hz RH)
1215, 4871686 *' ' *‘
1110:: 19F NMR (471 MHz, CDC13) 5 -111.85 4
4112.11 (1H),-112.15 4 4112.47 (111)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. ”C. 191:)
($11“ 1H NMR (400 MHz. CDC13) 8 12.06 (d, J
32;“? HRMS ESI
(/77 2') : 0.6 Hz. 1H). 8.33 (d. .1: 8.0 Hz. 1H).
‘298‘1‘ 7.98 (d. .1: 5.2 Hz. 1H). 7.45 4 7.40 (m.
(1MMy)
2107’ 2H), 7.40 — 7.35 (m. 2H). 7.28 — 7.18 (m,
calcd for
123 =
4 4H), 6.86 (d, .1: 5.2 Hz, 1H), 5.78 (dq, J
1736. C29HerO5. —
. . ,
,49.8. 6.1 Hz. 1H).4.61 44.45 (m. 1H).
1648 4.
“28‘ f01111d * 4.07 (d, J: 9.8 Hz, 1H). 3.94 (s. 3H).
{263’ 3.05 (s. 1H). 3.03 (s. 1H), 1.25 (d.J= 6.2
483 19 1’9
’ '
- Hz. 3H). 10401.1: 72 Hz. 3H)
(Thin
£122 1H NMR (400 MHz. CDC13) 5 12.12 (s,
2963* HRMS-ESI 1H). 8.37 (d. .1: 8.0 Hz. 1H). 7.98 (d. .1:
1735* (/77 z) 5.2Hz,1H),7.244 7.18 (111,411). 7.144
164E; ([M+H]+) 7.08 (m. 2H). 7.08 — 7.02 (m, 2H). 6.85
124 ”27’ calcd for (d..1:5.2 Hz. 1H). 5.80(dq..I: 10.1.
1480‘ CnggNzOs. 6.2 Hz. 1H). 4.63 4 4.40 (m. 1H). 3.99 (d.
1450’ 491.2540; J: 10.2 Hz. 1H), 3.93 (s, 3H), 2.65 —
1280’ found, 250 (m. 4H). 1.25 (d. J: 6.1 Hz. 3H).
126.; 491.2551 1.1851,]:76 Hz.3H)_ l.l4£t..]:7.6
Hz. 3H). 0.94 (4.14 7.2 Hz, 3H)
1142,
‘H NMR (400 MHz. CD(‘,1~,)5 1208 (d. .1
: 0.6 Hz. 1H). 8.33 (d. J: 8.0 Hz. 1H).
7.98 (d. J: 5.2 Hz. 1H), 7.32 — 7.20 (m,
5H). 7.19 4 7.10 (m. 1H). 6.97 (1. .1: 8.7
Hz. 2H). 6.86 (d. .1: 5.2 Hz. 1H). 5.78
HRgisz'fSl (dq, J: 10.0. 6.2 Hz. 1H). 4.58 — 4.45
([M+H]+) (m. 1H). 4.05 (d, J: 10.0 Hz, 1H). 3.94
(s. 3H). 1.26 (d. .1: 6.2 Hz. 3H). 0.98 (d.
calcd for
12$ ___ ___
J: 7 2 Hz 3H)
FNZOS: ‘ 5'
431931130 13C NMR (126 MHz. CDCL.) 8 171.63.
168.54. 161.72 (d..1:245.7 Hz). 155.35.
. -4 ;
433.1851
148.71,141.10,140.41.136.91(d.J=
3.5 Hz).130.42,129.58(d. J: 7.8 Hz),
128.59. 127.95. 126.84. 115.64 (d. .1:
21.3 Hz). , 73.39, 57.04, 56.07,
4783.19.15, 17.59
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NIVIR
N0. (‘0 (cm'l) (1H, 13C. 191:)
1H NMR (400 MHz, CD03) 8 11.77 (d, J
= 0.6 Hz, 1H), 8.25 (d, J: 8.0 Hz, 1H),
7.96 (d. .1: 5.2 Hz. 1H). 7.53 (dd. .7:
.0, 2.2 Hz, 2H), 7.35 (dd, J: 8.5, 1.8
Hz, 2H), 7.18 (ddd,J= 10.9, 8.5, 2.3 Hz,
2H). 6.88 (d. .1: 5.2 Hz. 1H). 5.80 (q. .7:
ESIMS 6.3 Hz. 1H). 4.68 4 4.47 (m. 1H). 3.95 (s.
m 2 589.5 3H), 1.27 (d, J: 7.3 Hz, 3H), 1.20 (d, J:
([M+H]+) 6.4 Hz, 3H)
”C NMR (126 MHz, CDC13)8 17098,
168.86,155.52,148.74,1441814199,
140.57. 132.92. 132.87. 132.02. 131.86.
130.48. 130,37. 12991. 128.15. 127.74.
125.09, 124.82, 109.64, 78.58, 74.60,
56.11, 48.05, 1756,1413
1H NMR (400 MHz. CD(‘,1~,)8 1 1.78 (d. .1
: 0.6 Hz, 1H), 8.25 (d, J: 8.0 Hz, 1H),
7.96 (d, J: 5.3 Hz, 1H), 7.33 — 7.27 (m,
2H). 7.22 (dd. .1: 10.4. 2.2 Hz. 1H). 7.08
(dddd. .1: 19.0. 8.5. 2.1. 0.8 Hz. 2H).
6.88 (d,J= 5.2 Hz, 1H), 5.82 (q, J: 6.3
Hz, 1H), 4.65 — 4.51 (m, 1H), 3.95 (s,
3H). 3.00 (s. 1H). 1.26 (d. .1: 7.2 Hz.
ESIMS 3H), 1.20 (d, J: 6.3 Hz, 3H)
m/z 333 .6
([M+H]+) 13C NMR (126 MHz. CDC1~,) 8 .
168.87. 15804 (d. .1: 249.8 Hz). 157.99
(d,J=249.5 Hz), 155.54, 148.76, 145.02
(d,J= 5.5 Hz), 142.77 (d,J= 6.0 Hz),
. 130.65. 130.55. 129.94. 122.05
(d,J: 3.7 Hz), 121.65 (d,J: 3.6 Hz),
120.45 (d, J: 17.8 Hz), 120.25 (d, J:
17.7 Hz). 114.56 (d. .1: 22.7 Hz). 114.26
(d. .1: 23.0 Hz). 109.62. 78.63. 74.64.
56.12, 48.02, 17.52, 14.30
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
1H NMR (400 MHz, CDC13) 5 12.06 (s,
1H), 8.32 (d,J= 8.0 Hz, 1H), 7.98 (d,J=
.2 Hz, 1H), 7.25 (d, .1: 9.7 Hz, 1H),
719 (d, J: 8.2 Hz, 1H), 7‘09 (dd, J:
, 4.0, 2.3 Hz, 2H), 7.02 (td,J= 8.5, 2.3 Hz,
IHU("IS')ESI 2H), 6.87 (d, .1: 5.2 Hz, 1H), 5.71 (dq, J
(MEN) : 10.0, 6.1 Hz, 1H), 4.54 (p, .1: 7.3 Hz,
1H), 3.99 — 392 (m, 4H), 2.33 (s, 3H),
calcd for
129 2.29 (s, 3H), 1.24 (d, J: 6.1 Hz, 3H),
C H27 29 C1 N 02 2 5. 1.07 (d, .14 7.2 Hz, 3H)2 '3
531.1448;
found, 13CNMR(126MHz,CDC13)o171.61,2
531.1454
168.57, 155.39, 148.74, 140.44, ,
139.35, , 136.15, 133.12, 132.77,
130.63,130.59,130.34, 129.45, 129.12,
126159, 126.41, 109.44, 73105, 56.45,
56.08, 47.85, 20.17, 2008, 19.15, 17.69
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. ”C. 191:)
(Thin
3376.
2986,
2360, 1H NMR (400 MHz. CDC13) 8 12.63 (s,
2107. 1H). 8.32 (d. .1: 7.9 Hz. 1H). 7.88 (d. J:
1736. 4.9 Hz. 1H). 7.62 (d. .1: 4.9 Hz. 1H).
1652, 7.29 — 7.15 (m, 4H). 7.05 — 6.85 (111,4H),
1604. 5.74 (dq. J: 9.9, 6.2 Hz. 1H). 4.61 —
1558. 4.48 (m. 1H). 4.05 (d. .1: 9.9 Hz. 1H).
1530, 1.25 (d,J: 6.1 Hz, 3H), 1.06 (d, J: 7.2
HRMS—ESI
15083 HZ, 3H)
,. (m z)
1452.
([M+HT) 1‘
1427. "C NMR (101 MHz. CDCL.) 8 171.39.
calcd for
130 1381, 167.69,161.76(d,J=246.1Hz).161.65
C H BrFN 0
1329, 245310769? 4’ (d,J=246.0Hz),155.39,139.43,136.82
1287. 5 161m * (d. .1: 3.4 Hz). 136.63 (d. .1: 3.1 Hz).
1262, 5210713 132.21,131.44,129.47(d,J: 8.0 Hz),
1247, ' 129.44 (c1, J: 7.9 Hz), . 115.76 (d,
1223. .1: 21.3 Hz). 115.42 (d. .1: 21.3 Hz).
1187. 73.47. 56.15. 48.05. 19.1 1. 17.61
1159,
1137, 19F NMR (471 MHz. CDC13) 5 -115.26 —
1116. —115.47(m).—115.64(ddd../: 13.7.8.9.
1049, 5.2 Hz)
1015, 911,
826. 792.
779. 729.
680, 668
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. 13C. 191:)
(Thin
33 3.
2940.
1739,
1651. 1
H NMR (300 MHz. CD(,1~.) 0 1201. . - (d. .1
-’ 881211281311115:1888»..=3.z...—.m,
?g 'FSI 5H). 6.88 (d. .1: 5.2 Hz. 1H). 5.66 (dq. J
1454‘ : 9.4. 6.2 Hz. 1H). 4.64 4 4.49 (m_ 1H).
(1110111)
4 ”'36: calcd for 4.01 (d, J: 9.4 Hz, 1H). 3.95 (s. 3H).
1382‘ C25H23F4N205~ 1:12 — 1.21 (111.4H). 1.16 (d. J— 7.2 Hz.3 )
1324. 5071538;
3:; 43331433 19F NMR (471 MHz. CDC13)5 -136.05 —
1210’ ' ' ' -136.27 (111). —136.61 (ddd. J: 20.1. 11.4.
1149‘ 8.1 H21. — 39.144 —139.32 (In).
1120; 439.43 — -l39.68 (m)
1054. 954.
924. 872.
850. 824,
801. 754.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd MP IR
NLASS NMR
N0. (‘0 (cm'l) (1H. 13C. 191:)
(11mm
3372.
2983,
1737,
1649.
1601.
1H NMR (300 MHZ,CDC13)512.02(d,J
1576,
= 0.6 Hz, 1H), 8.31 (d, J: 7.9 Hz, 1H),
1529, PDRBIS-ESI
7.97 (d. .1: 52 Hz. 1H). 7.27 (td, .1: 7.3.
1498. (/77 22)
2.1 Hz. 2H). 7.194 6.98 (m. 4H). 6.88 (d.
1481, (1M+HJ+)
J: 5.2 Hz, 1H), 5.66 (dq, J: 9.5, 6.1 Hz,
1453, calcd for
1H), 4.66 4 4.48 (m, 1H), 4.01 (d, J: 9.6
1439. C25H23C12F2N205.
Hz. 1H). 3.95 (s. 3H). 1.26 (d. .1: 6.2 Hz.
1381. 7;
3H),1,17(d,J: 7.2 Hz, 3H)
1323, fbund,
1245, 5590954
”F NMR (471 MHz. CDCI.) 5 -116.83 4
1184.
—1 16.94 (m). —1 17.22 4 —1 17.34 (m)
1145,
1096,
1060.953.
909.864.
849,824,
800,730,
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
(Thin
3372,
2935,
2257,
1735,
1649,
1576, 1H NMR (300 MHz, CDC13) 8 12.08 (d, J
1528, = 0.5 Hz, 1H), 8.34 (d, J: 8.0 Hz, 1H),
1501, 1112371752331, 7.97 (d, .1: 5.2 Hz, 1H), 7.12 4 6.98 (m,
1481, 5H), 6.97 4 6.79 (m, 3H), 5.70 (dq, J:
([M+H]+)
1452, 10.1, 6.1 Hz, 1H), 4.65 4 4.46 (m, 1H),
calcd for
133 1439, 3,94 (s, 3H), 2.21 (dd, .1: 9.8, 1.9 Hz,
C H (F N 0-
1380, 31952635, " 6H), 1.24 (d, .1: 6.1 Hz, 3H), 1.06 (d, .1:
1324, ' ‘ 7.2 Hz, 3H)
found,
1281’
499 2046
1262, ' ”P NMR (471 MHz, CD(‘,1~,)5 -119.78 4
1241, 4120.04 (m), 4120,30 4 4120.53 (In)
1206,
1 149,
1 1 18,
1051, 952,
908, 849,
821, 800,
1H NMR (300 MHz, CDC13) 8 12.08 (d, J
: 0.6 Hz, 1H), 8.20 (d, .1: 8.0 Hz, 1H),
8.00 (d, .1: 5.2 Hz, 1H), 7.26 4 7.13 (m,
4H), 7.02 4 6.83 (m, 5H), 5.69 (dq, J:
HRMS—ESI 90,62 Hz, 1H), 4.53 (dq, J: 8.0, 7,2
(m z) Hz, 1H), 4.05 (d, .1: 9.1 Hz, 1H), 3.96 (s,
(1M4Hr) 3H), 1.34 (d, J: 7.2 Hz, 3H), 1.22 (d, J:
calcd for 6.2 Hz, 3H)
135 ___ ___
F2N2054
471.1726; ”C NMR (126 MHz_CDC1~,)5171.27,
found, 168.54,162.68,162.58, 160.73, 160.63,
471.1742 155.43,148.77,140.44,136.81,136.78,
136,46, 136,43, 130.33, 129.72, 129.66,
129.63,129.57,115.74,115,57,115,43,
115.26,109.49, 73,33, 5611, 55.65,
47.80, 18.95, 17.74
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 19F)
1H NMR (300 MHz, CDC13) 8 12.00 (s,
1H), 8.30 (d,J= 7.8 Hz, 1H), 7.98 (CLJ:
.1 Hz. 1H). 7.42 4 7.28 (m. 4H). 7.09
(ddd,J: 10.1, 8.3, 2.2 Hz, 2H), 6.87 (d,
@1752?“ J: 5.2 Hz, 1H), 5.65 (dt,J= 12.2, 6.1
Hz. 1H). 4.57 (6.1: 7.3 Hz. 1H). 4.00
(IM+HI+)
(d, ./_: 9.6 Hz. 1H). 3.95 (s, 3H). 1.27 (d,
calcd for
136, J— 5.9 Hz, 3H), 1.17 (d, J— 7.2 Hz, 3H)
C25H23C14N205,
371910338 ”C NMR (126 MHz. CD(‘,1~,)5 171.45.
571101367 16864, 155.42, 148.74, 140.51, ,
' 140.16,133.11,132.76,131.70,131.38,
13097. 1306713027. 130.20. 13008,
. 127.17. 109.53. 72.38, 56.09,
5571,47.87,19.03,17.71
1H NMR (300 MHz, CDC13) 8 11.99 (s,
1H). 8.30 (d, .1: 8.0 Hz. 1H). 7.98 (d, .1:
52 Hz, 1H), 7,42 4 7.19 (m, 2H), 7.08 4
6.94 (m, 4H), 6.90 4 6.84 (m, 1H), 5.67
(dq, J: 9.4. 6.2 Hz. 1H). 4.65 4 4.48 (m.
HRMS-ESI 1H). 4.03 (d, .1: 9.4 Hz. 1H). 3.95 (s,
(m z) 3H), 1.27 (d, J: 6.1 Hz, 3H), 1.16 (d, J:
([M+H]+) 7.2 Hz, 3H)
13 ? ___ ___ cal0d for
CZSHBCIZFZNZOS, 1,:C NMR (126 MHz, CDC13)0 171.41,n ,,
539.0947; 168.64,158.16(d,J= 250.2 Hz), 158.01
found, (d, .1: 2501 Hz). 155.42. 148.75. 140.91
539.0953 (d, .1 : 61 Hz). 14083 (d, .1: 6.3 Hz).
140.51,131.12,130.81,130.20,12'-'1167—
12396 (111), 12011 (d, J: 17.5 Hz),
119.82 (c1. .1: 17.7 Hz). 116.78 2 116.06
(111), 109.52, 72144, 56.09, 47.85, 18199,
17.71
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (500 MHz, CDC13)8 8.27 (d, J
= 5.4 Hz, 1H), 8.13 (d, J: 8.0 Hz, 1H),
7.50 4 7.44 (111,414). 7.27 (ddd, J: 1 1.5,
8,5, 7.0 Hz, 4H), 7.20 4 714011211),
SI 6.94 (d, J: 5.4 Hz, 1H), 6.01 (q, J: 6.3
(m z) Hz. 1H). 5.75 4 5.62 (m, 2H). 4.63 4 4.52
[Ml' (m, 1H). 3.90 (s, 3H). 2.94 (s, 1H)_ 2.06
calcd for (s, 3H), 1.22 (d, J: 6.3 Hz, 3H), 1.03 (d,
C28H31.N308, J: 7.2 Hz, 3H)
522.2002;
found, ”C NMR (126 MHz, CDC13)5 171,88,
06 170.27,163.03,160.26, 145.73, 144.99,
143.90, 142.88, 142.57. 128.31. 128.28,
, 127.07, 125.56. 125.54. 109.58.
8949, 79.55, 75.21, 56.19, 48.10, 3093,
2087,1775, 1436
‘H NMR (400 MHz. CD(‘,1~,)8 8.41 (d. .1
: 78 Hz, 1H), 8.30 (d, J: 5.4 Hz, 1H),
7.38 — 7.10 (m, 10H), 6.97 (d, J: 5.4 Hz,
1H). 5.82 (dq. .1: 10.0. 6.2 Hz, 1H). 4.52
HRMS'ES',
(dt. .1: 8.2. 7.1 Hz. 1H), 4.05 (d. .1: 10.1
($171314) Hz, 1H), 3.87 (s, 3H), 2.37 (s, 3H), 1,24
(d,J= 6.1 Hz, 3H), 0.89 (d,J= 7.1 Hz,
calcd for
139 ___ ___ 3H)
(TZ7H36NZO(..
41312135 ’ ”C NMR (101 MHz, CDC13) 5 17223,
168.89. 162.28. 159.42. 146.66. 141.55,
4772019
141.44, 141,25, 137.45. 128.77. 128.50.
128.13,128.11,126.89,126.67,109.73,
73.32, 57.90, 56.27, 47.85, 20.75, 19.25,
17.92
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDClg) 8 8.35 (d, J
= 7.7 Hz, 1H), 8.30 (d, J: 5.4 Hz, 1H),
7.34 4 7.09 (m, 10H), 6.95 (d, J: 5.5 Hz,
1H), 5.81 (dq, J: 10.0, 6.2 Hz, 1H), 4.62
1111103175 )ESI_ — 4.44 (m, 1H), 4.05 (d, J: 10.0 Hz, 1H),
3.85 (s, 3H), 2.93 (hept. .1: 7.0 Hz. 1H).
(I MHZ”
1.34 (d, .1: 7.0 Hz, 6H), 1.24 (d. .1: 6.2
calcd for
140 Hz, 3H), 0.88 (d, J: 7.2 Hz, 3H)
C29H33N206,
3(£213 2 ”C NMR (101 MHz CD(‘,1~,) 8 174.69,
50%,2‘4 172.33, 162.28, 159.39, 146.56, 141.95,
“' 3
141.45,141.27,137.61,128.76,128.50,
128.14. 128.12.126.89. 126.67, 109.58.
73.28, 57.90, 56.27. 47.83, 33.94. 19.24,
18.82, 17.96
1H NMR (400 MHz, CDClg) 8 8.25 (d, J
: 5.4 Hz. 1H). 8.22 (d. .1: 7.9 Hz. 1H).
7,34 4 7.09011, 10H), 6.92 (d, J: 5.4 Hz,
, 1H), 5.83 (dq,J= 10.1, 6.2 Hz, 1H), 5.72
HRE‘ISBESI (d, .1: 0.7 Hz, 2H). 4.60 4 4.49 (m. 1H),
(MEN) 4.06 (d, .1: 10.1 Hz. 1H). 3.88 (s. 3H).
2.05 (s, 3H), 1,25 (d, J: 6.1 Hz, 3H),
calcd for
141 0.91 (d, J: 7.2 Hz, 3H)
“£23151; ”C NMR (101 MHz, CDCl;) 8 172.33,
_ 170.25,162.88,160.24, 145.70, 143.91,
507.2125
142.54. 141.48.141.25. 128.76, 12849,
128.12, 128.09, 126.89. 126.65. 109.56.
8950, 73.27, 57.92, 56.17, 48.07, 20.86,
19.25, 17.73
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
1H NMR (400 MHz, CDC13) 5 8.28 (d, J
= 7.9 Hz, 1H), 8.25 (d, J: 5.3 Hz, 1H),
7.36 4 7.08 (m. 10H), 6,92 (d, .1: 5.4 Hz.
1H), 5.83 (dq,J: 10.1, 6.2 Hz, 1H), 5.79
HRMS—ESI 4 5.69 (m, 2H), 4.62 4 4.44 (m, 1H), 4.06
(m z) (5. .1: 10.1 Hz. 1H), 3.86 (s. 3H), 2.53
(| M+H r) (hcpt, .1 : 7.0 Hz. 1H). 1.25 (d, .1 : 6.2
calcd for Hz, 3H), 1.13 (d, J: 7.0 Hz, 6H), 0.91
N307, (d. J: 7.2 HZ, 3H)
535.2444;
found, ”C NMR (101 MHz, CDC13) 5 17622,
535.2431 172.34,162.85,160.23, 145.55, 144.16,
. 141.48. , 128.76, 128.49,
128.12. 128,09. 12689. 126.65. 109.48.
89.90, 73.26, 57.93, 56.12, 48.07, 3385,
1926,1868, 1774
‘H NMR (400 MHz. CD(‘,1~,) 5 8.49 (d, .1
: 8.1 Hz, 1H), 8.31 (d, .1: 5.5 Hz, 1H),
7.214 7.13 (m, 2H), 7.03 4 6.97 (111,2H),
HRMS—ESI 6.95 4 6.86 (m. 3H), 5.54 (dq, .1: 7,3. 6.2
(177 z) Hz. 1H). 4.70 4 4.61 (m, 2H). 3.88 (s.
([M+H]+) 3H), 2.39 (s, 3H), 1.28 (d, .1: 6.2 Hz,
calcd for 3H), 1.17 (d, .1: 7.2 Hz, 3H)
(inH?Nzo?sz,
489.1154; ”C NMR (101 MHz, CDC13) 5 172.03,
found, 168.89,162.33,159.44, 146.66, 143.85,
489.1154 142.75. 141.50. 137.48, 126.75. 126.56,
126.06. 125,43. 12460. 124.55. 109.78.
74.58, 56.28, 47.96, 47.41, 20.76, 18.68,
18.14
‘H NMR (400 MHz. CD(‘,1~,) 5 8.30 (d, .1
: 7.9 Hz, 1H), 8.26 (d, .1: 5.4 Hz, 1H),
7.214 7.13 H), 7.02 (ddd,J= 3.5,
1.2. 0.6 Hz, 1H). 6.96 4 6.88 (111,411).
HREfZBES', 5.73 (d, .1: 0.7 Hz. 2H). 5.55 (dq_ .1:
([M+H]+) 7.4, 6.2 Hz, 1H), 4.75 4 4,60 (m, 2H),
calcd for 3.895(5, 3H), 2.06 (s, 3H), 1.29 (d, .1: 6.3
144 Hz. 3H). 1.19 (d, .14 7.2 Hz. 5H)
(721H57N207SZ.
3 #:1111259 ”C N1_V1R (101 MHz, CDC1_3) 5 172.13,
5191258 .162.91,160.26_ 145.69. 143.96.
143.86, 142,81, 142.46. 126.74, 126.55,
126.03, 125.42, 124.58, 124.54, 109.59,
89.52, 74.55, 56.19, 48.18, 47.42, 20.87,
18.70, 17.95
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 5 8.48 —
SI 8.37 (m, 1H), 8.30 (d, J: 5.4 Hz, 1H),
(m z) 7.29 4 7.18 (m, 4H). 7.05 4 6.90 (m, 5H),
(1M4Hr) 5,72 (dq, J : 9,7, 6.2 Hz, 1H), 4.55 (dq, J
calcd for = 8.3, 7.2 Hz, 1H), 4.05 (d, J: 9.6 Hz,
C27Hl—F3N306. 1H). 3.88 (s. 3H). 2.38 (s, 3H). 1.22 (d. J
5131837; : 6.1 Hz. 3H). 1.00 (d. .1: 7.2 Hz. 3H)
found,
513.1835 19F NMR (376 MHz, CDC13) 5
-115.58,-115.93
1H NMR (400 MHz, CDCl;) 5 8.26 (d, J
HRMS—ESI = 5.4 Hz, 1H), 8.22 (d, J: 7.8 Hz, 1H),
(m 2) 7,32 4 7.16 (m, 4H), 7,05 4 6.89 (m, 5H),
(1M4Hr) 5.78 4 5,68 (m, 1H). 5.72 (3,211). 4.64 4
calcd for 4.50 (m, 1H), 4.06 (d, J: 9.7 Hz, 1H),
C38H29F3N307, 3.90 (s, 3H), 2.06 (s, 3H), 1.24 (d, J: 6.1
5431943; Hz, 3H). 1.00 (d. .1: 7.2 Hz, 3H)
found,
543.1938 19F NMR (376 MHz, CDC13)5
—1 1559—11597
1H NMR (400 MHz.CDC1~,)5 8.34 (d. .1
= 7.9 Hz, 1H), 8.25 (d, J: 5.4 Hz, 1H),
7.39 — 7.16 (m, 10H), 6.94 (d, J: 5.4 Hz,
1H). 5.97 (q, .1: 6.2 Hz, 1H). 5.78 4 5.61
HRMS-ESI (m, 2H), 4.74 4 4.56 (m, 1H), 3.90 (s,
(m z) 3H), 3.42 (dq, J: 9.2, 7.0 Hz, 1H), 3.21
([M4Hr) (dq. J: 9.2. 7.0 Hz. 1H). 2.05 (3.311),
calcd for 1.25 (d. .1: 7.2 Hz, 3H), 1.19 (t. .1 : 6.9
C30H35N308, Hz, 3H), 1.12 (d, J: 6.3 Hz, 3H)
551.2393;
found. ”C NMR (101 MHz. CD(‘,1~,) 5 172.13.
96 17023,162.87,160.27, 145.64, 144.02,
142.35,142.09,140.72, 128.24, 127.84,
127.81. 127.70, 127.27. , 10957,
89.52, 84.04, 74.08. 59.96, 56.18. 48.26,
2086,1823, 1570,1495
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 8 8.26 (d, J
= 5.3 Hz, 1H), 8.22 (d, J: 7.8 Hz, 1H),
7.38 (td. J: 8.6, 6.2 Hz, 1H), 7.24 (td, J
HRMS-ESI : 84,63 Hz, 1H), 6.96 (d, J: 5.5 Hz,
(777 2) 1H), 6.88 — 6.69 (m, 4H), 5.88 — 5.75 (m,
([M4Hr) 1H), 5.73 (s. 2H), 4.69 (d, .1: 9.8 Hz;
calcd for 1H), 4.65 4 4.55 (m, 1H), 3.91 (s. 3H);
C28H37F4N307, 2.07 (s, 3H), 1,29 (d, J: 6.2 Hz, 3H),
579.1754; 110 (d,J= 7.2 Hz, 3H)
found.
579.1756 ”P NMR (376 MHz, CDC13) 8
-111.11 (d, J: 7.6 Hz), -111.57 (d, J:
75 Hz). —1 1 1.99 (dd, .1: 7.7, 2.6 Hz), —
112.76 (dd. J: 7.6, 2.5 Hz)
1H NMR (400 MHz, CDC13) 8 8.33 (d, J
= 7.9 Hz, 1H), 8.25 (d, J: 5.4 Hz, 1H),
7.40 4 7.18 (m, I()H)_6,94(d..1: 5.4 Hz,
HRMS-ESI 1H), 5.97 (q, J: 6.2 Hz, 1H),5.814 5.63
(m z) (m, 2H), 4.72 — 4.52 (m, 1H), 3.90 (s,
[M—OCHq+ 3H), 3.17 (s. 3H), 2.05 (s, 3H). 1.24 (d. J
calcd for : 7.2 Hz. 3H), 1.12 (c1. J: 6.3 Hz. 3H)
C28H29N207:
505.1975; ”C NMR (101 MHz, CDC13) 8 ,
found, 17024, 162.88, 160.27. 145.65. 144.02,
75 142,35,141.39,140.04, 128.50, 128.08,
127.87,127.71,127.45, 127.28, 109.57,
8953,8446, 73.815619525948125;
.86, 18.18, 14.98
1H NMR (400 MHz, CDC13) 8 8.39 (d, J
= 8.1 Hz, 1H), 8.31 (d, J: 5.4 Hz, 1H),
7.37 (td. J: 8.5, 6.1 Hz, 1H), 7.23 (td, J
SI : 8,5, 6.2 Hz, 1H), 7.00 (d, J : 5.5 Hz,
(777 2) 1H), 6.90 — 6.68 (m, 4H), 5.89 — 5.71 (m,
([M4Hr) 1H), 4.69 (d, J: 9.8 Hz, 1H), 4.62 4 4.51
calcd for (m, 1H). 3.90 (s, 3H). 2.39 (s, 3H)_ 1.28
C27H35F4N206, (d, J: 6.2 Hz, 3H), 1.09 (d, J: 7.2 Hz,
48; 3H)
found.
549.1645 ”P NMR (376 MHz, CDC13) 8
-111.11 (d,J=7.7 Hz), -111.55 (d,J=
75 Hz),-112101 (dd, J: 7.7, 2.6 Hz), —
112.80 (dd. J: 7.6, 2.6 Hz)
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
1H NMR (400 MHz, CDC13) 5 8.38 (d, J
HRMS—ESI = 8.2 Hz, 1H), 8.30 (d, J: 5.4 Hz, 1H),
(m z) 7.50 2 737 (m, 4H), 7.37 2 7.19 (m, 6H),
([M4Hr) 6.98 (d, J: 5.5 Hz, 1H), 5.98 (dq, J:
calcd for 25.1, 6.4 Hz, 1H), 4.63 4 4.54 (m, 1H),
C27H13FN306, 3,87 (s, 3H), 2.37 (s, 3H), 1.30 (d, .1: 6.5
495.1931; Hz, 3H). 0.88 (d, .1: 7.2 Hz, 3H)
found,
26 19F NMR (376 MHz, CDC13) 5
4168.48
1H NMR (400 MHz, CDCl;) 5 8.26 (d, J
= 5.3 Hz, 1H), 8.20 (d, J: 7.7 Hz, 1H),
HREiSZ'FSI, 7.49 4 7.40 H), 7,36 4 7.21 (111,611),
6.93 (5,.1: 5.5 Hz, 1H), 5.99 (dq. .1:
(1M+HJ+)
.2, 6.4 Hz, 1H), 5.71 (s, 2H), 4.68 4
calcd for
153 4.49 (m, 1H), 3.89 (s, 3H), 2.05 (s, 3H),
C H‘ W 0
33‘ 3“ ,3 7‘ 1.31 (d,.1: 6.5 Hz, 3H), 0.90 (d, .1: 7.2
Hz 3H)
found, ’
32320”
”P NMR (376 MHz. CDC1~,) 5
-168.67
1H NMR (400 MHz, CDC13) 5 8.42 (d, J
= 8.1 Hz, 1H), 8.30 (d, J: 5.4 Hz, 1H),
7.26 4 7.13 (m, 4H), 6.97 (d, .1: 5.5 Hz,
1H), 6.85 4 6.71 (m, 4H), 5.71 (dq, J:
HRMS—ESI 9.9, 6.2 Hz, 1H), 4.64 4 4.47 (m, 1H),
(m z) 396 (d, .1: 9.8 Hz, 1H), 3.87 (s, 3H),
(|M+Hr) 3.74 (s, 3H). 3.72 (s. 3H), 2.38 (s. 3H),
calcd for 1.22 (d, J: 6.1 Hz, 3H), 0.98 (d, J: 7.2
155” '
C29H33N208; Hz, 3H)
537.2237;
found, ”C NMR (101 MHz, CDC13)8 172,21,
537.2226 168.88,162.28,159.42, 158.33, 158.20,
146.66, 1411.53, 137.43, 133.90, 13382,
129.02, 129.00, 114.09, 113.83. 109.74.
73154, 5626.56.08, 55.19, 47.90, 20.74,
19.22, 18.08
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 8 8.41 (d, J
HRMS—ESI = 7.6 Hz, 1H), 8.31 (d, J: 5.5 Hz, 1H),
(m z) 7.32 2 7.18 (m. 2H). 7.12 2 6.82 (m. 7H).
(1M4Hr) 5.73 (dq, J : 9.7. 6.2 Hz, 1H), 4.64 4
calcd for 4.43 (m, 1H), 4.06 (d, J: 9.8 Hz, 1H),
C27H2—F3N30.,. 3.89 (s. 3H). 2.38 (s. 3H). 1.25 (d. .1: 6.2
513.1837; Hz. 3H). 0.99 (d. .1: 7.2 Hz. 3H)
found,
513.1833 19F NMR (376 MHz, CDC13) 8
-112.15.-112.56
1H NMR (400 MHz, CDC13)8 8.41 (d, J
= 7.7 Hz, 1H), 8.31 (d, J: 5.4 Hz, 1H),
7.314 7.10 (m. 8H). 6.99 (d. J: 5.5 Hz.
1H). 5.72 (dq. .1: 9,8. 6.0 Hz. 1H). 4.59
“1137473231351 — 4.50 (m, 1H), 4.01 (d, J: 9.8 Hz, 1H),
3.88 (s, 3H), 2.38 (s, 3H), 1.24 (d, J: 6.1
([M+H1+)
Hz. 3H). 1.00 (d. .1: 7.1 Hz. 3H)
calcd for
157 ___ ___
C73331231606 ”C NMR (101 MHz, CDC13) 8 172.10,
7 181111 ‘ 168.87. 162.33. 159.43. 146.68. .
142.44. 141.40. . 134.67. 134.38.
7545 1239" 130.21,129.95,128.46,128.34,128.10,
127.45,127.17,126.23, 126.13, 109.80,
72.61. 56.98. 56.28. 47.82. 20.75. 19.12.
17.98
1H NMR (400 MHz, CDClg) 8 8.26 (d, J
: 5.4 Hz. 1H). 8.23 (d. .1: 8.0 Hz. 1H).
7.24 4 7,14 (m. 4H). 6.93 (d. .1 : 5.4 Hz.
1H), 6.85 — 6.75 (m, 4H), 5.77 — 5.68 (m,
HRMS—ESI 1H), 5.72 (s, 2H), 4.63 — 4.50 (m, 1H),
(m z) 3.97 (d. .1: 9.9 Hz. 1H). 3.89 (s. 3H).
(1M4Hr) 3.75 (s, 3H), 3.73 (s, 3H), 2.05 (5,311),
calcd for 1.23 (d, J: 6.2 Hz, 3H), 0.99 (d, J: 7.2
(130143501209. HZ 3H)
567.2342;
found, 13C NMR (101 MHz, CDC13) 8 172.34,
38 170.24,162.88,160.24, 158.33, 158.20,
145.70. 14391. 142.54. . 133.82.
129.00,114.09,113.83,109.55,89.51,
73.49, 56.17, 56.10, 55.20, 48.12.2085,
19.23. 17.90
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 8 8.26 (d, J
= 5.4 Hz, 1H), 8.23 (d, J: 7.9 Hz, 1H),
7.32 4 7.18 H). 7.14 4 7.03 (m, 2H),
(£4313 7,04 4 6.80 (m, 5H), 5.82 4 5.67 (m, 1H),
.72 (s, 2H), 4.65 4 4.48 (m, 1H), 4.07 (d,
calcd for
159 .1: 9.9 Hz, 1H), 3.90 (s. 3H), 2.06 (s,
(,7 H71 RN70
72451943 7‘ 3H), 1.26 (d, .1: 6.1 Hz, 3H), 1.00 (d, .1:
* ' * 7.2 Hz, 3H)
found,
3411941
”P NMR (376 MHz. CD(‘,1~,) 8
41 12.16, 411259
1H NMR (400 MHz, CDClg) 8 8.26 (d, J
: 5.3 Hz. 1H), 8.22 (d, .1: 7.6 Hz. 1H),
.33 4 7,10 (m, 8H). 6.94 (d, .1: 5.4 Hz,
, 1H), 5.80 4 5,65 (m, 1H), 5.72 (s, 2H),
PRFHIYSZ'FSI 4.60 4 4.52 (m, 1H), 4.03 (d, J: 9.8 Hz,
1H), 3.90 (s. 3H), 2.06 (d, .1: 1.8 Hz,
(I M+H|+)
3H), 1.26 (d, J: 6.0 Hz, 3H), 1.02 (d, J:
calcd for
160 ___ ___ 7.1 Hz 3H)
C28H29C12N207, ’
57f“)? ”C NMR (101 MHz.CDCl¢,)5172.34,
572%,19 170.24,162.88,160.24, 158.33, 158.20,
" 145.70,143.91,142.54,1339513382,
129.00, 114.09, 113.83. 109.55. 89,51,
7349, 56.17, 56.10, 55.20, 48.12, 20.85,
19.23, 17.90
HRMs—ESI 1H NMR (400 MHz. CDC1,) 8 8.77 4
(m z) 8.53 (m. 1H), 8.40 4 8.29 (m, 1H). 7.79 4
([M+H]+) 7.62 (m, 3H), 7.61 4 7.47 (m, 1H), 7,47 4
calcd for 7.34 (m, 2H), 7.34 4 7.20 (m, 2H), 7.05 4
C27H37NZO(,, 6.94 (m. 1H), 5.83 4 5.66 (m, 1H). 4.93 4
475.1869; 477 (m, 1H), 4,37 4 4.21 (m, 1H), 3.89
found, (3, 3H), 2.47 4 2.37 (m, 3H), 1.63 4 1.47
4751865 (111,3H).0.84 4 0.67 (m, 3H)
”1134775231381 1H NMR (400 MHz, 8 8.58 ,
8.43 (m, 1H), 8.40 4 8.32 (m, 1H), 7.36 4
([M+H]+)
7.19 (m. 4H), 7.13 4 7.03 (111,4H), 7.02 4
calcd for
162 6.97 (m. 1H), 5.17 4 5.05 (m, 1H). 4.77 4
C7 H7—N70
4791-18 187? 4.64 (m, 1H), 4.35 4 4.19 (m, 1H), 396 4
161111d 7 3.85 (m, 3H), 2.40 (d, J: 3.6 Hz, 3H).
491.183 1.504 1.41 (111,3H). 1.07 4 0.93 (m, 3H)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
HRMS'ESI
1H NMR (400 MHz, CDC13) 8 8.52 7
(“$214) 837 (m. 1H). 8.32 7 8.24 (m. 1H). 7.80 7
7.63 (m. 3H). 7.61 7 7.47 (m. 1H). 7.45 7
calcd for
163 --- --- 7.22 (m, 4H), 7.01 — 6.92 (m, 1H), 5.83 —
C H «N O
36%; 973;? 5.68 (m, 3H), 4.97 7 4.73 (m, 1H), 4.38 7
‘ 16666“ 4.19 (m. 1H). 3.92 (s. 3H). 2.07 (s. 351).
1.64 71.49(m,3H),0.90 7 0,66 (16,5H)
5051961
HREiSZ'FSI 1H NMR (400 MHz. CDCL.) 5 8.39 7
8.25 (m. 2H). 7.39 7 7.20 (m. 4H). 7.15 7
(1MMy)
7.00 (m, 4H), 6.99 7 6.92 (m, 1H), 5.817
calcd for
164 5.72 (m, 2H), 5.16 7 5.09 (m, 1H), 4.79 7
(.7 END
53213924?“ 4.67 (m. 1H). 4.37 7 4.17 (m. 1H). 3.91
‘ foHnd * (s, 3H), 2.08 (s, 3H), 1.51 7 1.43 (m, 3H),
1.09 7 0.93 (m, 3H)
521.1913-
‘H NMR (400 MHz. CDCL.) 8 8.39 (d. .1
: 6.8 Hz, 1H), 8,31 (d, J: 5.4 Hz, 1H),
7.45 7 7.31 (m, 4H), 7.18 7 7.06 (m, 4H),
7.00 (d. .1: 55 Hz. 1H). 5.71 (dq, .1:
9.5.6.2 Hz. 1H). 4.65 7 4.46 (m. 1H).
($171314) 4.00 (d, J: 95 Hz, 1H), 3.89 (s, 3H),
2.38 (s, 3H), 1.22 (d, J: 6.2 Hz, 3H),
“a C1 d for
165 1.02 (d. .1: 7.2 Hz. 3H)
7BFZN2064
633 .0236;
”C NMR (101 MHz, CDC13) 8 172.05,
found,
168.89. 162.33. 159.47. 146.65. 141.39.
633 .0230
39.74. 139.71. 137.49. 131.97. 131.68.
129.89,129.78,121.06, , 109.84,
72.56, 56.41, 56.30, 47.83, 20.76, 19.09,
17.98
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDClg) 8 8.51 (d, J
= 8.1 Hz, 1H), 8.32 (d, J: 5.4 Hz, 1H),
6.99 (d. .1: 5.5 Hz. 1H). 6.74 (d. .1: 3.4
Hz, 1H), 6.67 (d, J: 2.6 Hz, 1H), 6.60 4
PRxSZfSI 6.42 (m, 2H), 5.53 4 5.59 (m, 1H), 4.72 4
4.38 (m. 1H). 4.44 (d. .1: 7.1 Hz. 1H).
”WHF)
3.88 (s. 3H). 2.41 4 2.38 (m. 9H). 1.27 (d.
calcd for
166 J— 6.2 Hz, 3H), 1.22 (d, J— 7.2 Hz, 3H)
Cstngzo?sz,
3 11,3111“ ”C NMR (101 MHz. CDCL.) 8 172.07.
168.90,16233,159.44, 146.66, ,
517 1465' “ 141.56,140.54,138.98,138.92,137.47,
125.77. 125.08.124.66. 124.42. 10976.
74.45. 56.28. 48.01. 47.83. 20.75. 18.64.
1821, 15.25
1H NMR (400 MHz, CDC13) 8 8.42 (d, J
: 8.0 Hz. 1H). 8.29 (d. .1: 5.4 Hz. 1H).
7.20 4 7.10(111,4H), 7.10 4 6.99 (m, 4H),
6.96 (d, J: 5.5 Hz, 1H), 5.77 (dq, J:
HRMs—ESI 10.0. 6.2 Hz. 1H). 4.65 4 4.45 (m. 1H).
(m z) 3.98 (d. .1: 10.0 Hz. 1H). 3.85 (s. 3H).
([M+H]+) 2.37 (s, 3H), 2.26 (s, 3H), 2.23 (s, 3H),
calcd for 1.23 (d, J: 6.1 Hz, 3H), 0.93 (d, J: 7.1
NZO(,. Hz. 3H)
505.2338;
found, ”C NMR (101 MHz, CDC13) 8 172.23,
505.2345 168.90. 162.28.159.42. 146.67. 14158.
138.67, 138.57, 137.44. . 136.02.
129.41,129.11,127.94,127.91,109,74,
7344, 57.06, 56.27, 47.91, 20.97, 2094,
.76, 19.26, 17.99
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 8 8.36 (d, J
= 8.8 Hz, 1H), 8.29 (d, J: 5.4 Hz, 1H),
7.19 4 7.12 (111,4H). 7.10 4 6.98 (111,411).
6.94 (d, J: 5.5 Hz, 1H), 5.76 (dq, J:
SI 10.0, 6.2 Hz, 1H), 4.60 — 4.45 (m, 1H),
(m z) 3.97 (d, .1: 9.9 Hz, 1H), 3.84 (s, 3H),
(1M4Hr) 3.00 4 2,85 (m, 1H). 2.26 (s, 3H). 2.24 (s,
calcd for 3H), 1.34 (d, J: 7.0 Hz, 6H), 1.22 (d, J:
C31H3-N306, 6.1 Hz, 3H), 0.93 (d, J: 7.2 Hz, 3H)
533.2651;
found, ”C NMR (101 MHz, CDC13) 8 174,69,
533.2655 ,162.28,159.39, 146.57, 141.98,
.138.59,137.60_ 136.31. 13601,
129.40, 129.10, 127.95. 127.93, 109.58,
7340,5705, 5627,4789, 3395,2097,
2094, 19.25, 18.84, 18.04
‘H NMR (400 MHz. CD(‘,1~,)5 8.26 (d, .1
: 5.4 Hz, 1H), 8.21 (d, J: 7.8 Hz, 1H),
7.45 — 7.33 (m, 4H), 7.22 — 7.03 (111,4H),
6,95 (d, .1: 5.4 Hz, 1H), 5.83 4 5.61 (m,
HRMS'ES',
1H), 5.72 (s. 2H), 4.56 (p, .1: 7.3 Hz,
($171314) 1H), 4.01 (d, J: 9.6 Hz, 1H), 3.90 (s,
3H) 2.06 (s, 3H), 1.24 01:1: 6.2 Hz,
621168 for
169 5H), 1.02 (d, .14 7.2 Hz, 3H)
(szquBerzoz.
”C NMR (101 MHz, CDC13) 8 172.18,
found,
170.25, 162.91, 160.27, 145.69. 143.97,
66303
142.36, 39.81,139,71_131.97_ 131.68,
129.87,129.76,121.06, 120.77, 109.63,
89.49, 72.51, 56.46, 56.20, 48.06, 20.87,
19.12, 17.81
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDClg) 8 8.31 (d, J
= 7.9 Hz, 1H), 8.27 (d, J: 5.3 Hz, 1H),
6.94 (d. .1: 5.4 Hz, 1H). 6.75 (d, .1: 3.4
Hz, 1H), 6.70 4 6.62 (m, 1H), 6.57 4 6.50
HRMS—ESI (m, 2H), 5.77 4 5.70 (m, 2H), 5.52 4 5.40
(777 2) (m, 1H), 4,75 2 4.58 (m, 1H), 4.45 (d, J:
(119141113 7.1 Hz, 1H)_ 3.90 (s. 3H). 2.40 (d. .1: 1.2
calcd for Hz, 3H), 2.39 (d, J: 1.1 Hz, 3H), 2.06 (s,
C36H31N30783, 3H), 1.36 4 1.14 (m, 6H)
found, ”C NMR (101 MHz, CDC13)5 172.17,
547.1585 170.25,162.90,160.26, , 143.95,
. 141.64. . 138.96. .
125.73, 125.07, 124.65. 124.41. 109.55.
89.54, 74.42, 56.18, 48.23, 47.85, 2087,
1866,1803, 1524
‘H NMR (400 MHz. CDCL.) 8 8.33 4
8.15 (m, 2H), 7,2 4 7.10 (m, 4H), 7,10 4
6.99 (m, 4H), 6.92 (d, J: 5.4 Hz, 1H),
5844569 (In, 3H).4.55 (11-1: 7.3 Hz.
HRMS'ES',
1H). 3.99 (c1, .1: 10.0 Hz, 1H). 3.87 (s,
($171314) 3H), 2.27 (s, 3H), 2.24 (s, 3H), 2.05 (s,
3H), 1.24 (d, J: 6.2 Hz, 3H), 0.95 (d, J:
“?led for
171 7 2 Hz 3H)
CmstNzOm ‘ ‘ 5
3312:? ”C NMR (101 MHz, CDC13) 8 172.34,
170.24, 162.87. 160.24. 145.70. 143.90,
535 24419
142.59, 138,70. 138.58. 136.32. 135.99.
129.40,129.10,127.93, 127.90, 109.55,
89.51, 73.38, 57.07, 56.17, 48.12, 20.96,
.93, 20.86. 19.26, 17.81
1H NMR (300 MHz, CDC13)8 8.42 (d, J
HRMS—ESI = 7.7 Hz, 1H), 8.31 (d, J: 5.4 Hz, 1H),
(m 2) 7,60 , 7‘50 (m, 2H), 7,47 2 7.37 (m. 2H).
(119141113 7.34 4 7,13 (m, 5H). 6.99 (d. .1 : 5.4 Hz.
calcd for 1H), 5.83 (dq, J: 9.6, 6.2 Hz, 1H), 4,65
C38H38F3N306, 4 4.45 (m, 1H), 4.14 (d, J: 9.7 Hz, 1H),
5451899; 3.88 (s, 3H). 2.38 (s. 3H). 1.25 (d. .1: 6.2
found, Hz, 3H), 0.92 (d, .1: 7.2 Hz, 3H)
545.1902
”F NMR (376 MHz. CDCL.) 8 -62.56
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (300 MHz, CDClg) 5 8.40 (d, J
= 8.1 Hz, 1H), 8.30 (d, J: 5.5 Hz, 1H),
7.314 7.12 (m, 8H). 6.99 (d, J: 5.5 Hz,
HRMS-ESI 1H), 5.72 (dq, J: 9.5, 6.1 Hz, 1H), 466
(m z) 4 4.47 (m, 1H), 4.03 (d, J: 9.5 Hz, 1H),
([M4Hr) 3.88 (s,31—1)_ 2.38 (s, 3H), 1.22 (d, .1: 6.1
calcd for Hz, 3H). 1.01 (d, J: 7.1 Hz, 3H)
C27H27C12N2065
545.1246; ”C NMR (75 MHz, CDC13) 5 172.06,
found, , 162.33, 159.45. 146.66. 141.36,
545.1244 139,32,13927,137.47, 132.94, 132.69,
129.51,129.41,129.01,128.72,109.85,
72.70, 56.30, 56.27. 47.83, 20.75, 19.09,
17.98
1H NMR (300 MHz, CDC13) 5 8.26 (d, J
= 5.4 Hz, 1H), 8.22 (d, J: 7.8 Hz, 1H),
HRS/7178;“, 7.58 4 7.49 (m, 2H). 7.42 (d, J : 8.2 Hz,
2H), 7.35_4 7,12 (m, 5H), 6.95 (d, J : 5.4
([M+H]+)
_ calcd for Hz, 1H), 5.84 (dq, J: 9.8, 6.2 Hz, 1H_),
175 5,72 (s, 2H). 4.62 4 448 (m, 1H). 415 (d,
OH RN70
[8575112005 7‘ J: 9.8 Hz. 1H), 3.90 (s. 3H), 2,06 (s,
" “ 3H), 1.26 (d,J= 6.1 Hz, 3H), 0.93 (d,J=
found,
7 2 Hz 3H)
575.201 1 ‘ ’
”P NMR (376 MHz, CDC13)8 -62.57
1H NMR (300 MHz, CDClg) 5 8.26 (d, J
: 5.4 Hz. 1H), 8.22 (d, J: 7.8 Hz, 1H),
7.34 4 7,09 (m, 8H). 6.95 (d, J : 5.4 Hz,
SI 1H), 5.81 4 5.58 (m, 3H), 4.67 4 4.44 (m,
(m z) 1H), 4.04 (d, J: 9.5 Hz, 1H), 3.90 (s,
(|M+Hr) 3H), 2.06 (s. 3H), 1.24 (d, J: 6.2 Hz,
calcd for 3H), 1.02 (d, J: 7.1 Hz, 3H)
C28H29C12N207:
575.1352; 13C NMR (75 MHz,CDC1~,)5 172.19,
found, 170.28, 162.91, l6(),27_ 145.71. 143.95,
575.1352 142.32,139.38,139.28, , 132.67,
129.49, 129.40, 129.01, 128.71, 109.64,
89.47, ?2.65, 56.32, 5622, 56.18. 48.05,
2089, 20.86, 19,12,1781
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. ()0 (cm'l) (H, ”C, 191:)
(Thin
3387,
2984,
1737, 1H NMR (400 MHz, CDC13) 5 8.35 (dd, J
1673, : 4.5, 1.3 Hz, 1H), 8. 15 (d, J: 78 Hz,
1603, SI 1H), 7.52 (dd, .1: 8,4, 1.4 Hz, 1H), 7.42
1579, (m z) (dd, J: 84,45 Hz, 1H), 7.33 — 7.14 (m,
1506, ([M+H]+) 4H), 7.05 — 6.86 (m, 4H), 5.82 (s, 2H),
1451, calcd for 5.72 (dq, .1 : 9.7, 6.1 Hz, 1H), 459 (p, .1
1368, C27H17F3N206, : 73 Hz, 1H), 4.06 (d, J: 9.7 Hz, 1H),
1304, 5131832, 2.11 (s, 3H), 1.24 (d, J: 6.2 Hz, 3H),
1268, found, 101 (d, .1: 72 Hz, 3H)
1199, 5131833
1159, 1”F NMR (376 MHz, CDC13) 5
1136, -115.57,-115.97
1045,
1007, 969,
825, 779,
(Thin
3380,
2985,
1737,
1674,
1603, 1H NMR (400 MHz, CDC];) 5 8.23 (d, J
1578, : 5.3 Hz, 1H), 8.18 (d, .1: 7.8 Hz, 1H),
HRMS'ESI
1507, 7.23 (ddd, J: 13.9, 6.9, 2.6 Hz, 4H),
1473, 314) 705 — 6.84 (111,5H), 5.78 — 5.66 (m, 3H),
1455, 4.56 (p, .1: 7.3 Hz, 1H), 4. 12 (q, .1: 7.0
calcd for
179 1366, Hz, 2H), 4.05 (d,J: 9.7 Hz, 1H), 2,06 (s,
C H F N 0
1312, 22531289; 7’ 3H), 1.47 (t, J: 7.0 Hz, 3H), 1.24 (d,J=
1274, * ' ' ‘ 62 Hz, 3H), 1.00 (d, .1: 7.2 Hz, 3H)
found.
1222*
557 2089
1200, ~ ' ' 1”F NMR (376 MHz, CDC13) 5
1158, -115.60,-115.98
1 104,
1043,
1003, 968,
910, 886,
824, 792,
[Annotation] Mel.Chan
None set by Mel.Chan
ation] an
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
(Thin
3404,
2983,
1737,
1652, 1
H NMR (400 MHz, CD(,1~.) 5 8. 13 (dd, .1, , ,
1508‘ :79, 1.8 Hz, 1H), 8.06 (d,J:6.9 Hz,
1482’ SI 1H), 7.45 (ddd, J: 8.5, 7.4, 1.8 Hz, 1H),
1453, (777 2) 7,29 2 7.05 (m, 6H), 7.04 2 6.90 (m, 4H),
1369‘ (| M4Hr) 5.92 (d, .1: 6.4 Hz, 1H), 5.83 (d. .1: 6.4
calcd for Hz, 1H), 5.73 (dq, J: 9.9, 6.2 Hz, 1H),
180 1305’
1222’ CstngzNo?, 4.57 (p, J: 7.1 Hz, 1H), 4.06 (d, J: 9.7
512.1879; Hz, 1H), 2.14 (s, 3H), 1.25 (d, .1: 6.0 Hz,
1 197‘
_ found, 3H), 1,00 (d, J: 7.2 Hz, 3H)
1159,
512.1889
’ 19
F NMR (376 MHz, CDC1~,) 5
41562 —11601
1088, ‘ ~ ~ ~
1049,
1010, 976,
91 1, 828,
792, 759,
‘H NMR (400 MHz, CD(‘,1~,)5 8.24 (t, .1
: 77 Hz, 2H), 7.57 4 7.49 (m, 8H), 7,45
— 7.37 (m, 8H), 7.32 (dt, J: 9.3, 5.8 Hz,
2H), 6.90 (d, .1: 5.4 Hz, 1H), 5.89 (dq, J
HRMS-ESI : 12.4, 6.1 Hz, 1H), 5.71 (s, 2H). 4.58 (p,
(m z) J: 7.3 Hz, 1H),4.16 (d,J= 10.0 Hz,
([M+H]+) 1H), 3.88 (s, 3H), 2.05 (s, 3H), 1.33 (d, J
calcd for : 6.1 Hz, 3H), 0.96 (d, .1: 7.2 Hz. 3H)
C411H39N2073
659.2752; ”C NMR (101 MHz, CDC13) 5 172.38,
found, 170.26, 162.88, 160.23, 145.68, 14394,
6592758 142.52, 140.73, 140.61. 140.52. 140.23,
139.89,139.63,128.74,128.71,128,55,
12755, 127.26, 127.17, 126.99, 12696,
109.50, 89.54, 73.27, 57.25, 56.15, 48.12,
20187, 19.34, 17.79
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd. MP IR NMR
“L133,
No. (0C) anrb CH,”C_”F)
IHNMRomOMMLCDC9584u¢J
=51H;1H1&%M¢J=54HL1H1
7577747mL8Hy74ldeé93.60
1u.&41732(dd21:121,111u,311
694(d“]=55]?;11D,588(dq¢]=
In?deSI/ 123.61H11H1457@“P:72HL
(W??f) 1HL4U(dJ:HMHt.Hu387@
?DJ38®3HL1M1¢J=61Hz
mkdbr
1& u- u— ¢J=11H;J?
QJkN?m
612L316; ”C NMR (101 MHZ, CDC13)8 17224.
6292651 16229,15940,14663.14152
' ' 14062.140A7_14023.13988.
13962.13745.12875_12871.12856.
12725,12716,12700,12696,
10969,7330,5722,5625,4790,2075,
m3Ln97
‘HNmemOMHLCDcmsgzng
=54HL1H1815¢J:56H21H1
7257?15m14ny7037689m15Hy
5757566mL3H141lde:181
57H21H14mu¢J=91HL1H1
, 392(&3}D,389(dd¢l=183.5411;
I??gifSI 1H121M(g3H1124¢1J:621u.
(1M+H1+>
C ‘31:? $0
13C NMR (126 MHZ. CDC1~,) 5 170.32.
’gnéléli “ 16911.16172(d”1:246()Hz)16162
Zb'nde (d“1==245.4I{z),160.31,145.73,
-?u ’ 1M0213211%67@WEQ6ZHA
5301809
129.72. 129.66. 1 15.68 (d. .1: 21.5 Hz).
11541 (d, J: 22.1 Hz), 109.65, 89148.,
73.37, 56.16, 55.69, 41.33, 20.87
wFNMRQ?lMHzCDGQé
-115.60 (111), -115.94 (111)
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (500 MHz, CDC13) 5 8.26 (d, J
= 5.4 Hz, 1H), 8.22 (d, J: 8.4 Hz, 1H),
7.28 4 7.18 (m. 4H). 7.01 4 6.90 (m. 5H).
.77 4 5.65 (m, 3H), 4.56 (ddd, J: 8.4,
6.7, 5.3 Hz, 1H), 4.05 (d, .1: 9.6 Hz, 1H),
391 (s, 3H). 2.06 (s. 3H). 1.63 4 1.52 (m.
1H). 1.40 4 1.29 (m. 1H). 1.23 (61.7: 6.2
”11374735381 Hz, 3H), 0.61 (t, J = 7.4 Hz, 3H)
(3:111); ”C NMR (126 MHz. CD(‘,1~,)5 171.56.
184 170.27,163.06,161.72(d,J:246.0 Hz),
C H F N 0
225;;12312; 7’ 161.66 (d,J= 2452 Hz), 160.32, 145.66,
”10116d ‘ 144.03. 142.38. 136.92. 129.60 (d. .1:
.6 Hz). 129.54 (d. .1: 10.4 Hz). 115.63
“558 2133' (d,J=35.4 Hz), 115.46 5.4 Hz),
109.55, 89.59, 73.22, 56.19, 56.02, 55.26,
.24. 20.87. 19.22, 9.16
19F NMR (471 MHz, CDC13)8
4115.59 4 41 15.70 (m). 41 16.06 (ddd. .1:
14.0. 8.7. 5.3 Hz)
1H NMR (500 MHz, CDC13) 5 8.29 4
8.21 (m, 2H), 7.29 4 7.14 (m, 4H), 7.00 4
6.88 (m. 5H). 5.85 4 5.51 (m. 3H). 4.55
(dd, J: 9.3, 4.6 Hz, 1H), 4.05 (d, J: 9.6
Hz, 1H), 3.91 (s, 3H), 2.06 (s, 3H), 1.87 4
1.75 (m. 1H). 1.22 (d. .1: 6.2 Hz. 3H).
0.78 (d. .1 : 6.9 Hz. 3H). 0.58 (d. .1: 6.8
HRMS-ESI
Hz, 3H)
(777 z)
(3:111); ”C NMR (126 MHz. CD(‘,1~,) 5 171.17.
185 170.27, 163.21, 161.70 (d,J:246.1 Hz),
C H~~F7N 0
; 7’ 161.66 (d, J: 2453 Hz), 160.38, 145.62,
* fo11nd‘ ‘ 144.11. 142.32. ; 129.54.429.54
(4.1: 14.9 Hz). 1 15.6.» (d. .1: 32.3 Hz).
572.2286
115.46 (d, J: 32.3 Hz), 109.54, 89.63,
7325,5714, 597, 3109,2088,
1927. 19.10. 17.06
19F NMR (471 MHz, CDClg) 5
-115.69(ddd..l: 13888.55 Hz).
41 16.12 (5615.7: 138. 8.7. 5.5 Hz)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 19F)
1H NMR (500 MHz, CDC13) 5 8.25 (d, J
= 5.4 Hz, 1H), 8.07 (d, J: 8.8 Hz, 1H),
7.28 4 718011.411). 7.01 4 6.91 (m. 5H).
.74 4 5.66 (m. 3H), 4.57 (ddd, J: 9.6,
8.7, 5.1 Hz, 1H), 4.04 (d,J= 9.9 Hz, 1H),
3.90 (s. 3H). 2.06 (s. 3H). 1.41 4 1.31 (m.
1H). 1.23 (d..1:6.1 Hz. 3H). 1.224 1.17
y (m, 1H), 1.04 — 0.96 (m, 1H), 0.79 (d, J:
HREVHIYSZ'FSI 6.5 Hz, 3H), 0.74 (d, J: 6.6 Hz, 3H)
); ”C NMR (126 MHz, CDC13) 5 172.38,
186 170.29, 163.06, 161.73 (d, J: 245.7 Hz),
C H _F N 0
28:92:10; 7’ 161.67 (d. .1: 2454 Hz). . 145.57.
7 161115 ‘ 144.14. 142,22. 13717. . 129.57
(d,J= 12.1Hz), 129.50 (d,J= 11.8 Hz),
58; 2409"
115.64(d,J=35.1Hz),115.47(d,J=
.0 Hz). 109.55. 89.60. 73.08.5620.
56.19, 50.69, 41.20, 24.56, 22.80, 21.63,
.87, 19.19
”P NMR (471 MHz.CDC1~.)5
-115.66 (td,J= 9.1, 4.7 Hz), -116.21
(ddd,J= 13.9, 8.7, 5.3 Hz)
‘H NMR (500 MHz. CDCL.) 5 8.38 4
8.23 (m, 2H), 7.27 4 7.12 (m, 4H), 7.10 4
6.83 (m, 5H), 5.69 (dq, J: 9.1, 6.2 Hz,
1H). 4.13 4 3.95 (m. 2H). 3.92 (s. 4H).
.39 (s. 3H). 1.23 (61.1 : 6.2 Hz. 3H)
HRMS—ESI
(m 2) ”C NMR (126 MHz, CDC13) 5 168.98,
(|M+H|+) 168.92. . 161.71 (d../:245,8 Hz).
calcd for 16162 (d, J: 245.4 Hz), 159.51, 146.67,
C26H35F3N306, 141.23, 137.55, 136.79, 136.53 (d,J=
499.1675; 3.4 Hz). 12972 (d. .1: 2.9 Hz). 129.65
found. (d. .1 : 2.7 Hz). 1 1567 (d. .1: 21.3 Hz).
499.1664 115.40 (d, J: 21.3 Hz), 109.89, 73.42,
56.31, 55.71, 41.17, 20.73.1911
”P NMR (471 MHz, CDC13) 5
-115.55 4 -115.66 (m), -115.95 (rt, .1:
8.3. 4.0 Hz)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
1H NMR (500 MHz, CDC13) 5 8.39 (s,
1H), 8.32 (d, J: 5.5 Hz, 1H), 7.33 4 7.04
(m, 4H), 7.06 4 6.86 (m, 5H), 5.70 (dq, J
: 9,4, 6.1 Hz, 1H), 4.54 (ddd, J: 8,6,
6.5, 5.4 Hz, 1H), 4.04 (d, J: 9.4 Hz, 1H),
3,91 (s, 3H), 2.38 (s, 3H), 1.62 4 1.49 (m,
1H), 1.40 4 1.30 (m, 1H), 1.22 (d, .1: 6.1
“1157475231351 Hz, 3H), 0.59 (t, J: 7.4 Hz, 3H)
(321C112); ”C NMR (126 MHz, CD(‘,1~,)5 171.41,
188 168.90, 162.46, 161.71 (d,J:245.9 Hz),
C H F N 0
22279198; 6’ 161.66 (d,J= 245.4 Hz), 159.46, 146.63,
' foHnd ‘ 141.46, 137.48, 136.88, 129.63 (d, .1:
7.8 Hz), 129.53 (d, .1: 7.8 Hz), 115.67
'527 1981' (d,J=21.3Hz),115.40(d,J=21.1Hz),
109.74, 73.25, 56.30, 55.96, 53.02, 25.54,
.76, 19.20, 9.04
19F NMR (471 MHz, CDC13) 5
4115.62 4 41 15.72 (m), 41 16.07 (td, .1:
9.3, 8.9, 4.1 Hz).
1H NMR (500 MHz, CDC13) 5 8.35 (s,
1H), 8.31 (d, J: 5.4 Hz, 1H), 7.35 4 7.16
(m, 4H), 7.08 4 6.80 (m, 5H), 5.70 (dq, .1
: 9,5, 6.1 Hz, 1H), 4.51 (dd, .1: 9.5, 47
Hz, 1H), 4.04 (d,J= 9.5 Hz, 1H), 3.91 (s,
3H), 2.38 (s, 3H), 1.89 4 1.68 (m, 1H),
1.21 (d, .1: 6.3 Hz, 3H), 0.76 (d, .1: 6.9
SI Hz, 3H), 0.58 (d, J: 6.9 Hz, 3H)
(777 z)
(|M+H|+) ”C NMR (126 MHz, CDCL.) 5 ,
calcd for , , 161.69 (d, J: 245.9 Hz),
C29H31F3N206, 161.65 (d, J: 244.8 Hz), 159.46, 146.61,
541.2145, 1415413748, 13697 (d, 7:33 Hz),
found, 136.88 (d, .1: 3.4 Hz), 129.65 (d, .1: 7.9
541.2143 Hz), 129.52 (d,J= 8.0 Hz), 115.66 (d,J
= 21.3 Hz),115,41(d,J= 21.3 Hz),
109.71, 73.25, 56.95, 56.30, 55.91, 20.77,
19.25, 18.99, 17.09
19F NMR (471 MHz, CDC1~,) 5
4115.67 4 4115.78(m), -116.06 4
-116.17 (In)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (500 MHz, CDC13) 8 8.30 (d, J
= 5.5 Hz, 1H), 8.18 (d, J: 8.2 Hz, 1H),
7.35 4 7.13 (m, 4H). 7.04 4 6.80 (m, 5H),
.68 (dq, J : 9.8, 6.2 Hz, 1H), 4.54 (td, J
= 9.2, 5.2 Hz, 1H), 4.03 (d, J: 9.7 Hz,
1H), 3.90 (s. 3H), 2.38 (s, 3H). 1.20 (dd,
.1: 16.3. 6.1 Hz, 4H). 1.04 (ddd. .1:
13.9, 8.7, 5.2 Hz, 1H),0.914 0.81 (m,
HRMS—ESI 1H), 0.78 (d, J: 6.4 Hz, 3H), 0.73 (d, J:
(m z) 6.6 Hz, 3H)
(lM+HJ+)
calcd for ”C NMR (126 MHz, CDC13) 8 172.20,
NZOG, 168.87, 162.46, 161.7] (d, .1: 2457 Hz),
555.2301; 161.66 (d. .1: 245.4 Hz), 159.46. ,
found, 141.50, 137.48, 137.07 (d,J= 3.3 Hz),
555.2292 13689 (d, J: 3.3 Hz), 12960 (d, J: 8.0
Hz), 129.50 (d,.1: 8.0 Hz), 11568 (d,./
: 21.3 Hz), 115.40 (d, J: 21.3 Hz),
109.71, 73.08, 56.23, 50.54, 24.54, 22.76,
21.71,20.76,19.16
1”F NMR (471 MHz, CDC13) 5
415.59 4 -115.77 (111), -116.14 4
41 16.29 (111)
(11m 1H NMR (300 MHz, CDC13)8 8.32 4
?lm) HRMS—ESI 8.19 (m, 2H), 7.47 (dd, J: 7.7, 1.8 Hz,
338]. (m z) 1H), 7.23 (s. 1H), 7.24 4 7.04 (m, 2H),
2937, (| M+Hr) 6.93 (d, .1 : 5.5 Hz, 1H), 6.93 4 6.77 (m,
1735, calcd for 3H), 6.78 (dd, J: 8.3, 1.2 Hz, 1H), 5.95
1676, C30H35N309, (dq, J: 9.9, 6.2 Hz, 1H), 5.78 4 5.66 (m,
1492, 5672335; 2H), 5.01 (d, .1: 9.8 Hz, 1H), 4.62 4 4.48
1245, found, (m, 1H), 3.90 (s, 3H), 3.85 (3,311), 3.76
1203, 567.2337 (3, 3H), 2.06 (s, 3H), 1.24 (d, J: 6.2 Hz,
1042 3H), 0.95 (d, .1: 7.2 Hz, 3H)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 19F)
1H NMR (300 MHz. CDC13) 8 8.27 (d, J
(Thin
= 5.4 Hz. 1H), 8.23 (d. J: 7.8 Hz. 1H),
HRMS-ESI 7.26 4 7.14 (m. 1H). 7.16 (LJ: 7.9 Hz.
2938‘ (m 2) 1H). 6.93 (d, J: 5.4 Hz, 1H), 6.92 4 6.87
1737’ ([M+H]+) (m, 2H), 6.87 — 6.80 (m. 2H), 6.73 (ddd,
1675, calcd for J: 8.2. 2.6. 0.9 Hz. 11-1). 6.69 (ddd. J:
192 ___
1583‘ (T;UH~.5N30«,. 8.2. 2.6. 0.9 Hz. 1H). 5.79 (dq. J: 9.7.
1%04’ 567.2341; 5.8 Hz, 1H). 5.73 — 5.69 (m, 2H).4.71—
1488, found, 444 (m. 1H), 3.99 (d. J: 10.2 Hz. 1H),
1202‘ 567.2337 3.90 (s. 3H). 3.77 (s. 3H). 3.76 (s. 3H).
1041‘ 2.06 (s, 3H), 1.25 (d, J: 6.1Hz,3H),
0.94 (d, J: 7.2 Hz, 3H)
(Thin 1H NMR (400 MHz. CDC1~.) 5 8.24 (dt. J
?lm) HRMS-ESI : 5.4. 1.3 Hz. 1H). 7.99 (d../: 8.1 Hz.
3378, (m 2) 1H), 7.81 (t. J: 8.5 Hz. 1H), 7.36 (t, J:
2983, ([M+H]+) 8.5 Hz, 1H), 7.19 — 7.10 (m, 1H). 7.07 —
1741. calcd for 6.98 (m. 1H). 6.99 4 6.86 (m. 3H). 6.14 4
193 ___
7 1672, C28H37C13F3N208, 6.04 (m, 1H), 5.70 (d. J: 6.4 Hz. 1H),
1575, 02; 5.64 (d. J: 6.4 Hz. 1H). 4.66 (p. J: 7.2
1483. found. Hz. 1H). 3.92 (s. 3H). 3.82 (s. 1H). 2.07
1201. 627.1107 (5. 3H). 1.35 (d. J: 7.2 Hz. 3H). 1.22 (d.
1002 J: 6.9 Hz. 3H)
1H NMR (300 MHz. CDC13) 5 8.27 (d, J
: 5.4 Hz. 1H). 8.23 (d. J: 7.8 Hz. 1H).
(Thin
HRMS-ESI 7.15 4 7.02 (m, 2H), 7.00 4 6.84 (m, SH),
(m z) 5.76 — 5.63 (m, 3H). 4.66 — 4.49 (m, 11-1),
([M+H]+ 2984’ ) 3.97 (d. J: 9.8 Hz. 1H). 3.91 (s. 3H).
calcd for 2.20 (d. J: 1.9 Hz. 3H). 2.18 (d.J: 1.8
___ 1738‘
1675) F3N307, Hz, 3H), 2.06 (s, 3H). 1.24 (d, J: 6.2 Hz,
”04’ 571.2257; 3H), 1.02 (d, J: 7.2 Hz, 3H)
120 1‘ _f0L111d._ w
1003‘ 571.225 F NMR (471 MHz, CDC13)OA
-116.63 (t.J= 9.5 Hz). -117.12 (t. J: 9.5
(Thin
HRMS-ESI 1 . A
?lm) H_NMR (300 MHZ, CDClg) 0 8.27 (d, J
(m z) = 5.4 Hz. 1H), 8.23 (d. J: 7.9 Hz. 1H),
3377 +
2983’ ([M+H] ) 7.25 4 7.20 (m. 2H). 7.17 4 7.02 (m. 4H).
calcd for 6.94 (d. J: 5.4 Hz. 1H). 5.75 4 5.62 (m.
___ 173; ' 1675) C30H33C13N207, 3H), 4.68 — 4.50 (m. 1H), 3.95 (d. J: 9.9
”01’ 603.1657; Hz, 1H). 3.91(s, 3H). 2.31 (s, 3H), 2.28
17202‘ found. (5. 3H). 2.06 (s. 3H). 1.24 (d. J: 6.1 Hz.
1050‘ 603.1659 3H). 1.03 (d, J: 7.2 112,311)
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
$1131 1H NMR (400 MHz. CDC13) 8 8.26 (d, J
HRMs—ESI : 5.4 Hz. 1H). 8.13 (d. .1: 8.1 Hz. 1H).
587‘ (m z) 7.85 (11.7: 7.6. 1.9 Hz. 1H). 7.47 (11. .1:
1741’ ([M+H] ) 7.7, 1.8 Hz, 1H), 7.28 4 7.20 (m, 1H),
calcd for 7.22 — 7.11 (m, 2H), 7.09 — 6.99 (m, 11-1),
___ 16733
1507 szHwFZNZOX. 7.01 4 6.79 (m. 3H). 6.29 4 6.20 (m. 1H).
1486‘ 559.1884; 5.71 (d,J:6.4 Hz, 1H),5.67(d,J:6.4
1453’ found, Hz, 1H), 4.75 4 4.57 (m, 1H), 3.91 (s,
1203’ 559.1886 3H). 3.48 (d. .1: 6.1 Hz. 1H). 2.07 (s.
3H). 1.34 4 1.21 (111.6H)
(Thin
3379. SI 1H NMR (300 MHz. CDCL.) 8 8.27 (d. .1
3282, (m z) = 5.4 Hz, 1H), 8.21 (c1, J: 7.8 Hz, 1H),
2984, ([M+H]+) 7.46 4 7.34 (m, 5H), 7.26 4 7.15 (111,311),
2107. calcd for 6.94 (d. .1: 5.4 Hz. 1H). 5.87 4 5.68 (m.
1738, C33H31N207, 3H), 4.62 4 4.48 (m, 1H), 4.07 (d, J : 9.8
1674, 555.2125, Hz, 1H), 3.91 (s, 3H), 3.05 (s, 1H). 3.03
1503. found. (5. 1H). 2.06 (s. 3H). 1.34 4 1.22 (111.3H).
1202. 555.2126 0.98 (d. .1: 7.2 Hz. 3H)
1043,
($11111 1H NMR (300 MHz. CDCL.) 5 8.27 (d, .1
33219) HRMS E81
2') = 5.4 Hz, 1H), 8.23 (c1, J: 7.8 Hz, 1H),
2964’ 7.24 4 7.18 (111,4H), 7.14 4 7.03 (m, 5H),
([M+H1+)
1736‘ 6.93 (d. .1: 5.5 Hz. 1H). 5.87 4 5.69 (m.
calcd for
198 16‘75‘ 3H), 4.53 (p, J: 7.3 Hz, 1H), 3.99 (d, J:
C37H~9N707
”05’ 53" 10.1Hz, 1H), 3.90 (d,J= 1.0 Hz, 3H),
1202’ ‘ 1611116 ‘ 2.68 4 2.48 (m. 4H). 2.06 ((1.7: 1.1 Hz.
1042‘ 3H). 1.24 ((17:71 Hz. 3H). 1.224 1.10
563 2722
1003’ ‘ ' “ (m, 6H), 0.88 (d, J: 7.2 Hz, 2H)
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 8 8.27 (d, J
= 5.3 Hz, 1H), 8.21 (d, J: 7.9 Hz, 1H),
7.31 4 7.22 (m. 5H). 7.21 4 7.12 (m. 1H).
7.00 4 6.81 (m,3H),5.814 5.74 (m, 1H),
HRMS—ESI 5.72 (d, J: 0.8 Hz, 2H), 4.54 (p, J: 7.2
(m z) Hz. 1H). 4.05 (d. J: 9.9 Hz. 1H), 3.90 (s.
(119141117) 3H). 2.06 (s. 3H). 1,24 (d. .1 : 6.2 Hz.
calcd for 3H), 0.92 (d, J: 7.2 Hz, 3H)
199 ___ ___
CZ8H3UFNZO7:
525.2032; ”C NMR (126 MHz. ~,)5 .
found, 17028, 162.87, 161.70 (d, J: 245.6 Hz),
525.2045 160.25,145.69,143.97, 142.50, 141.20,
137.03 (d, .1: 3.3 Hz), 129.60 (d, .1: 7.8
Hz). 128.59. 128.02. 126.80. 11560 (d. .1
= 21.3 Hz), 109.52, 89.55, 73.11, 5704,
56.18, 48.05, 20.87, 19.18, 17.74
‘H NMR (400 MHz. CD(‘,1~,)5 8.26 (d. .1
: 5.4 Hz, 1H), 7.89 (d, J: 8.0 Hz, 1H),
7.56 (d, J: 2.2 Hz, 1H), 7.48 (d, J: 2.2
Hz. 1H). 7.34 (dd. .7: 8.5. 4.2 Hz. 2H).
7.18(ddd_.1: 10.5. 8.4. 2.2 Hz. 2H).
6.97 (d, J: 54 Hz, 1H), 5.79 (q, J: 6.3
Hz, 1H), 5.68 (d,J= 6.3 Hz, 1H), 5.61
ESIMS (d. .1: 6.4 Hz. 1H). 4.63 4 4.52 (m. 1H).
m z 661.1 3.92 (s, 3H), 3.55 (s, 1H), 2.07 (s, 3H),
([M+H]+) 1.27 (d, J: 7.2 Hz, 3H), 1.18 (d, J: 6.3
Hz. 3H)
13C NMR (126 MHz, e-(1’6) 5
166.30,165.13,158.33,155.10,140.60,
39.16. 138.49. 137.43. 137.10. 127.58.
126.60,126.48,125.21, 123.17, 122.62,
119.99, 119.77, 104.55, 84.15, 73.35,
69.04. 51.05. 43.24. 26.40. 15.69920
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NIVIR
N0. (‘0 (cm'l) (1H, 13C. 191:)
1H NMR (400 MHz, CDC13) 8 8.26 (d, J
= 5.4 Hz, 1H), 7.91 (d, J: 8.0 Hz, 1H),
.33 4 7.27 (m. 3H). 7.21 (dd. .1: 10.4.
2.1 Hz, 1H), 7.11 (ddd, J: 8.5, 2.2, 0.8
Hz, 1H), 7.06 (ddd,J= 8.6, 2.1, 0.9 Hz,
1H). 6.97 (d. .1: 5.4 Hz. 1H). 5.80 (q. .1:
6.3 Hz. 1H). 5.68 (d. .1: 6.3 Hz. 1H).
.61 (d, J: 6.3 Hz, 1H), 4.63 — 4.51 (m,
1H), 3.92 (s, 3H), 3.54 (s, 1H), 2.07 (s,
3H). 1.25 (d. .1: 7.2 Hz. 3H). 1.18 (61.7:
ESIMS 6.4 Hz, 3H)
202 m/Z 627.1
(WT) 13C NMR (126 MHz. CDC1~,) 8 171.43.
170.32. 163.50. 160.30. 157.99 (d. .1:
249.5 Hz), 157.96 (d, J: 249.3 Hz),
145.76, 145.20 (d, J: 5.8 Hz), 143.73,
143.09 (d. .1: 6.1 Hz). 142.58. 13053 (d.
J: 3.2 Hz), 122.14 (d, J: 3.8 Hz),
121.85 (d,J= 3.5 Hz), 120.23 (d,J=
17.8 Hz). 120.05 (61.1: 17.8 Hz). 114.70
(d. .1 : 22.5 Hz). 114.34 (d. .1: 23.0 Hz).
109.72, 89.34, 78.60, 74.30, 56.24, 48.39,
.94, 20.86, 443
‘H NMR (400 MHz. CDC1,) 8 8.27 (d. .1
: 5.4 Hz, 1H), 8.21 (d, J: 7.8 Hz, 1H),
7.26 — 7.19 (m, 2H), 7.10 (dd,J= 8.5, 2.2
Hz. 2H). 7.03 (ddd. .1: 13.4. 8.2. 2.3 Hz.
2H). 6.94 (d. .1: 5.5 Hz. 1H). 5.77 4 5.62
HRMS-ESI (m, 3H), 4.56 (p, J: 7.2 Hz, 1H), 3.95
(m z) (d,J= 10.0 Hz, 1H), 3.91 (s, 3H), 2.33
(I M+H l+) (s. 3H). 2.31 (s. 3H). 2.06 (s. 3H). 1.23
calcd for (d, J : 6.1 Hz, 3H), 1.00 (d, J : 7.2 Hz,
C30H33C12N207, 3H)
603. 1 659;
found. ”C NMR (126 MHz. CD07.) 8 172.30.
603. 1666 170.28,162.90,160.27, 145.70, 143.97,
142.42,139.64,139.47, 136.51, 136.11,
133.06. 13271. 130.74. . 129.42.
, 126.63, 126.49, 109.57, 89.52,
72.78, 56.44, 56.19, 48.06, 20.87, 20.17,
.09. 19.19 17.82
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 8 8.40 (d, J
= 7.9 Hz, 1H), 8.32 (d, J: 5.5 Hz, 1H),
7.30 4 7.22 (m, 6H). 7.19 4 7.13 (m, 1H),
7,014 6.93 (m, 3H), 5.76 (dq, J: 9,8, 6,2
HRMS—ESI Hz, 1H), 4.58 4 4.49 (m, 1H), 4.05 (d,J=
(m z) 9.9 Hz, 1H), 3.90 (s. 3H), 2.38 (s. 3H),
(1M4Hr) 1.23 (d, .1: 6.1 Hz, 3H), 0.90 (d. .1: 7.2
calcd for Hz, 3H)
204 "_ --_
CZ7H2‘FNZO6:
495.1926; ”C NMR (126 MHz, CD(‘,1~,)5 172.19,
found, 168.90, 162.27, 161.69 (d, J: 245.6 Hz),
159.42,146.64,141.51,141.14,137.46,
137.02 (d, .1: 3.2 Hz), 129.60 (d, .1: 7.8
Hz), 128.59. . 126.81, 11559 (d, .1
= 21.2 Hz), 109.72, 73.14, 56.99, 5628,
47.81,20.74,19.15,17.92
‘H NMR (400 MHz. CDCL.) 8 8.40 (s,
1H), 8.32 (d, J: 5.4 Hz, 1H), 7.22 (dd, J
= 17.1, 8.2 Hz, 2H), 7.09 (dd,J= 7.2, 2.2
Hz, 2H). 7.06 4 6.96 (m, 3H), 5.69 (dq, J
HRMS'ES',
: 9.9, 6.2 Hz, 1H), 4.61 4 4.47 (m. 1H),
($171314) 3.96 4 3.92 (m, 1H), 3.90 (s, 3H), 2.38 (s,
3H), 2.32 (s, 3H), 2.30 (s, 3H), 1.22 (d, J
calcd for
206 4 6.2 Hz. 3H), 0.99 (d. .14 7.2 Hz. 3H)
CdeON01,,
3 13111134 ”C NMR (126 MHz, CDC13) 8 172.16,
573153;] 168.91.162.3015945, 146.64. 141.45,
39.58, 137.47, 136.50. 136.10. ,
132.71,130.73,130.63,129.41,129.12,
126,64,126.51, 109.76, 7282, 56.34,
47.83, 20.75, 20.16, 2009, 19.16. 18.00
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. ”C. 191:)
1H NMR (500 MHz, CDC13) 8 8.30 (d, J
= 5.5 Hz, 1H), 8.29 (br s, 1H), 7.26 —
7.18 (m. 4H). 7.01 4 6.88 (m. 5H). 5.70
(dq. J: 9.5, 6.1 Hz, 1H). 4.64 4 4.48 (m.
1H), 4.04 (d, .1: 9.5 Hz, 1H), 3.88 (s,
3H). 1.39 (s. 9H). 1.22 (d. .1: 6.1 Hz.
HRMsiFAB (m z) 3H). 0.99 (d. .1: 7.1 Hz. 3H)
([M+H]+)
calcd for ”C NMR (126 MHz, CDC13) 8 176.0,
207 ‘6; (gquFlNZO... 172.3. 162.2. 161.7 (d. .1: 245.8 Hz).
‘ 555.2301; 161.6 (d,J:245.6 Hz), 1594. 1465,
found. 1421,1378, 136.9, 136.8, 129.6 (d,J=
555.2311 8.0 Hz). 1295 (d. J: 7.8 Hz). 115.7 (d. .I
: 21.3 Hz). 115.4 (d. .1: 21.3 Hz). 109.5.
73.0, 56.3, 56.1, 47.8, 39.1, 27.2, 19.1,
”P NMR (471 MHz. CDC13)8
-115.7, -116.0
1H NMR (400 MHz. CDCL.) 8 8.30 (d. J
: 5.4 Hz. 2H). 7.28 4 7.14 (m. 4H). 7.02
— 6.89 (m, 5H), 5.70 (dq, J: 9.5, 6.2 Hz,
1H). 4.63 — 4.48 (m, 1H), 4.04 (d, J: 9.5
HRMS-ESI Hz. 1H). 3.87 (s. 3H). 2.93 (11861. .1: 7.0
(m z) Hz, 1H), 1.34 (d. .1: 7.0 Hz. 6H), 1.22
([M+H]+) (d, J: 6.2 Hz, 3H), 0.98 (d, J: 7.1 Hz,
calcd for 3H)
208 ___ ___
CwHHFZNZOO.
541.2145; 13C NMR (126 MHz, CDC13) 8 174.69,
found, 172.21.162.69,162.61, 162.28, 16074,
9 160.66. 159.43. 146.54. 141.81. 137.65.
136.86.136.84,129.64, 129.57, 129.51,
115.76,115.59,115.46,115.30.109.61,
73.03. 56.29. 56.07. 47.79. 33.94. 19.12.
18.80. 18.04
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 8 8.45 —
8.25 (m, 2H), 7.30 — 7.15 (m, 4H), 7.05 —
6.86 (m. 5H). 5.71 (dtd. .1: 9.7. 7.3, 6.8,
55 Hz, 1H), 453 (n, J : 83, 6.6 Hz,
1H), 4.04 (d, .1: 9.6 Hz, 1H), 3.88 (d, J:
m’ls'ESI,
1.2 Hz, 3H), 3.80 (td. .1: 6.6. 1.2 Hz.
:34) 2H). 3.39 (d, .1: 1.2 Hz, 3H). 2.97 (td, .1
= 67,13 Hz, 2H), 1.22 (dd,.1= 6.3.1.3
calcd for
209 Hz, 3H), 0.98 (dd, J— 7.2, 1.3 Hz, 3H)
C2«>H31F2N207.
3511;621:199 ”C NMR (126 MHz, CDC13)8 172.13,
169.42,162.70,162.61,162.25,160.74,
“557 20914' 160.66, . 146.69, 141.44. 137.34,
136.87. 136.84, 136.81. . 129.56,
129.50,115.77,115.60,1154111530,
109.78, 73.06, 67.57, 631, 5608,
47.81. 34.62. 19.12.1799
1H NMR (400 MHz, CDCl;) 8 8.33 (dd, J
= 19.6, 5.4 Hz, 2H), 7.25 — 7.16 (m, 4H),
7.03 4 6.88 (m, 5H). 5.70 (dq, .1: 95, 6.2
Hz, 1H). 4.65 4 4.52 (m, 1H). 4.04 (61.1:
9.6 Hz, 1H), 3190 (s, 3H), 1.95 (16.1:
HREVHIYSZ'FSI, 80,46 Hz, 1H), 1.25 (dd, J: 4.6, 3.1
Hz, 2H). 1.22 (d. .1: 6.2 Hz, 3H)_ 1.05
(I WHF)
(dt, J: 8.1, 35 Hz, 2H), 098 (d, J: 72
calcd for
210 ___ ___ Hz 3H)
C29H29F2N206, ’
:11?“ ”C NMR (126 MHz. CDCL.) 8 172.45,
,0“ ° 172.20, 162.70, 162.61, 162.26, 160.74,
539.1988
160.66,159.50,146.56, 141.80, 137.45,
136.87, 136.85, , 129.64. 129.57.
129150,115,76,115.59,115,47,115.30,
109.68, 73.03, 56.31, 56.08, 47.75, 19.13,
18.09, 13.00, 9.27
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 5 8.25 (t, J
= 6.2 Hz, 2H), 7.32 — 7.11 (m, 4H), 7.04
4 6.85 (m. 5H). 5.79 4 5.65 (m. 3H). 4.55
(p, J : 7.3 Hz, 1H), 4.04 (d, J : 9.7 Hz,
511321753581 1H), 3.87 (s, 3H), 2.53 (hept, J: 7.0 Hz,
1H). 1.23 (d. .1: 6.2 Hz. 3H). 1.12 (d. .1:
(IM+HI+)
7.0 Hz. 6H)_ 0.99 (d. .1: 7.2 Hz. 3H)
calcd for
21 1 ___ ___
C3glgigjio7 ”C NMR (126 MHz, CDC13) 5 176.25,
‘ fo11nd * . 162.88. 162.70. 162.60. 160.74.
, 160.26, 145.54, 144.21, 142.02,
571 225'
136.94,136.92,136.86, 136.83, 129.60,
129.56. 129.54.129.49. 115.77. .
115.47. 115.30. 109.53. 89.88. 73.01.
56.13,48.05,33.85,19.15,1866,1781
1H NMR (400 MHz, CDClg) 5 8.23 (dd, J
: 16.1. 6.6 Hz. 2H). 7.25 4 7.18 (m. 4H).
7.02 4 6.89 (m, 5H), 5.82 4 5.66 (111,3H),
4.54 (p, J: 7.3 Hz, 1H), 4.08 (s, 2H),
HRMS—ESI 4.04 (d. .1: 9.7 Hz. 1H). 3.89 (s. 3H).
(m z) 3.58 (q. .1 : 7.0 Hz. 2H). 1.25 4 1.20 (m.
([M+H]+) 6H), 0.99 (d, J: 7.2 Hz, 3H)
calcd for
212 ___ ___
(gqugFZNZOx. 1~”C NMR (126 MHz. CD(‘,1~.)0 172.20.a
587.2199; 170.05,162.84,162.70, 162.61, 160.75,
found, 160.65,160.21,145.73, 143.95, 142.23,
587.2217 136.95. 136.92.136.85. 136.83. 129.60.
129.56. 129.54. 129.50. 115.78. 115.61.
115.47,115.30, , 89.55, 73.04,
67.78, 67.17, 56.23, 56.14, 53.46, 48.04,
19.15.17.81.15.00.1495
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (400 MHz, CDC13) 8 8.45 —
8.22 (m, 2H), 7.30 — 7.15 (m, 4H), 7.04 —
6.89 (m. 5H). 5.71 (dq. .1: 9.5. 6.2 Hz.
1H), 4.63 4 4.45 (m, 1H), 4.04 (d, J: 9.6
HRMS—ESI Hz, 1H), 3.89 (s, 3H), 2.68 (t, J: 7.6 Hz,
(777 z) 2H). 1.76 (p. .1: 7.6 Hz. 2H). 1.54 4 1.37
(| M+H|+) (m. 2H). 1.22 (d. .1 : 6.1 Hz. 3H). 1.06 4
calcd for 0.88 (m, 6H)
213 ___ ___
C30H33F2N206a
555.2301; ”C NMR (126 MHz. CDCL.) 8 172.17.
found, ,162.70,l62.61, 162.31, 160.74,
160.66,159.47,146.56, 141.61, 137.57,
136.87. 136.85. 136.82. 129.63. 129.57.
129.50. 115,76. 115.60. 115.47. 115.30.
109.69, 73.05, 56.26, 56.08, 47.80, 33.64,
29.70, 26.61, 22.20, 19.12, 18.02, 1376
(Thin
3388,
2970.
2363.
2029,
1738,
1677.
1604,
1508, HRMS—ESI 1H NMR (400 MHz, CDClg) 8 8.28 (d, J
1449. (m z) : 7.8 Hz. 1H). 8.17 (d. .1: 4.9 Hz. 1H).
1414. (|M+Hr) 7.68 (d. .1: 4.9 Hz. 1H). 7.30 4 7.16 (m.
1366, calcd for 4H), 7.05 — 6.90 (m, 3H), 5.81 — 5.69 (m,
1307, BrF3N306, 3H), 4.54 (p, J: 7.3 Hz, 1H), 4.05 (d, J:
1218. 593.0921; 9.8 Hz. 1H). 2.09 (s. 3H). 1.59 (s. 1H).
1203, found, 131 4 1.21 (m, 3H), 1.00 (d, J : 7.2 Hz,
1159, 593 .0925 3H)
1 139.
1 1 13.
1042,
1000, 970,
908. 831.
806, 793,
778, 731,
71 1. 682.
670. 663
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. ”C. 191:)
(Thin
3380.
2985,
2362,
1769.
1738. 1H NMR (300 MHz. CDCL) 5 8.38 (d. .1
1674, = 8.0 Hz, 1H). 8.32 (d, J: 5.4 Hz, 1H),
1609, 7.18—6.88 (m, 7H), 5.64 (dq.J= 9.5.6.3
1591. “$752331 Hz. 1H). 4.64 4 4.47 (m. 1H). 4.00 (d. .1:
1572, 93 Hz. 1H), 3,91 (s, 3H). 2.39 (s, 3H).
([M+H]+)
1513, 1.23 (d,J= 6.1 Hz, 3H), 1.09 (d, J: 7.2
“led for
215 1434 Hz 3H)
‘ ‘
6 C27H25F4N206.
1367*
549 1643
1310, “ foHnd ‘ 11JF NMR (471 MHz, CDC13) 5 -136.31
1277, (ddd,J= 20.1, 11.2, 8.2 Hz), -136.74
549 16;;
1202. ‘ ' “ (ddd..l:2().3. 11.3. 7.8 Hz). 439.144 —
1175, 139.50 (111), —139,70 (dddd,J: 21.4,
1150, 10.6, 7.7, 4.1 Hz)
1 1 13.
1051.
1009, 952.
907, 825,
805. 731.
668, 657
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd MP IR
NLASS NMR
190. (‘0 (cnf? (1H. 13C. 191:)
(11mm
3375.
2984,
2361,
2132.
1770.
1738,
1676, 1H NMR (300 C13)5 8.38 (d, J
1590. : 8.3 Hz. 1H). 8.31 (c1. .1: 5.4 Hz. 1H).
1H1RdS-ESI
1572, 7.26 (ddd, J: 11,5,7.2,2.1Hz,2H),
(n72)
1499, 7.18 — 6.95 (m, 5H), 5.63 (dq, J: 9.3, 6.1
1452. Hz. 1H). 4.65 4 4.49 (m, 1H). 4.00 ((1.7:
Cdcd?n
216 1437. 9.4 Hz. 1H). 3.91 (s. 3H). 2.39 (s. 3H).
C27H25C12F2N 206:
1367, 1.24 (d, J: 6.2 Hz, 3H), 1.09 (d, J: 7.2
581.1052;
131L Hz, 3H)
found.
1251.
581.1061
1199, ”P NMR (471 MHz, CDC13)8 -116.85 4
1175, -117.26 (111), -117.29 — -117.50 (In)
1098.
1061.
1010,952,
907,828,
805,782.
764,733,
687,668,
657,651
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd MP IR N1\1IR
N0. (‘0 (cm'l) (1H, 13C. 191:)
(11mm
33 3.
2983.
1771,
1736.
1676.
159L 1H NMR (300 MHz. CDC13) 8 8.40 (d, J
1572. = 8.2 Hz, 1H). 8.32 (d. J: 5.4 Hz, 1H),
1503. 1H{RJS-ESI 7.14 4 6.96 (m. 5H). 6.96 4 6.81 (m. 2H).
1451. (/77 Z) 5.68 (dq, J: 9.9, 6.1 Hz. 1H). 4.53 (dt. J
1437, ([M+H1+) = 8.2, 7.1 Hz, 1H). 3.94 (d,J= 10.0 Hz,
1366. cmcd?n 1H). 3.90 (s. 3H). 2.38 (s. 3H). 2.22 (dd.
1311. (729H21F2N206. .1: 6.7.1.9 Hz. 6H). 1.21 (d. .1: 6.1 Hz.
1271 541.2145; 3H), 0.98 (d, J: 7.1 Hz, 3H)
1237. found.
1201. 541.2156 ”P NMR (471 MHz. CD(‘,1~,)5
1176, —119.90 4 —120.14(m). 0 4
1119, -12065(nD
1099.
1051.
1009.949.
907.825.
733.668.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. ”C. 191:)
(Thin
3376.
2988.
2363,
1742.
1675. 1H NMR (300 MHz. CDCL.) 8 8.27 (d. .1
1609, = 5.4 Hz. 1H). 8.21 (d. J: 7.8 Hz. 1H),
1580. 7.18 — 6.85 (111.7H).5.72(s,2H). 5.65
1515. SI (dq. .1: 10.5. 6.2 Hz. 1H). 4.58 (p. .1:
1454. 7.3 Hz. 1H). 4.01 (d. J: 9.4 Hz, 1H).
1435, calcd for 3.913s. 3H). 2.07 (s. 3H). 1.25 (d. J: 5.9
218 1.368. Hz. 5H). 1.09 (d. .14 7.2 Hz. 5H)
szHl—HNzOz.
1310*
579 1749
1284, ' foHnd ‘ 11)F NMR (471 MHz. CDC13) 5
1236. —136.29 (ddd.J= 20.1. 11.2, 8.0 Hz). —
1203. ‘S79 1762' 136.73 (ddd. .1: 20.1. 11.3. 8.0 Hz). —
1181, 139.16 4 —139.43 (m). -139.64 4
1149, -139.84 (In)
1 120.
1043.
1004. 970.
910. 873.
829. 754.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd MP IR ‘NBIR
NLASS
190. (‘0 (cnf? (1H, 13C. 191:)
(11mm
3393.
2986,
2364,
1742. ‘H NMR (300 MHz. ~,) 5 8.27 (dd. .1
1676.
:54, 1.1 Hz, 1H), 8.21 (d,J: 7.8 Hz,
1580,
1H), 7.35 — 7.19 (m, 2H), 7.20 — 7.01 (m,
1499,
PHRRJS-ESI 4H). 6.96 (dd. .1: 5.5. 1.1 Hz. 1H). 5.72
1454.
(/77 22) (d. .1: 1.1 Hz. 2H). 5.64 (dddd. .1: 11.6.
1437,
([M+H]+) 9.1, 5.3, 3.3 Hz, 1H), 4.65 — 4.51 (m,
1408,
calcd for 1H), 4.01 (d, .1: 9.5 Hz, 1H), 3.92 (d, J:
219 1367.
(123H27C13F3N307. 1.1 Hz. 3H). 2.07 (c1. .1: 1.1 Hz. 3H).
1310.
611.1158; 1.304121 (111,311), 1.09(dd,J: 71.11
1250,
fbund, Hz, 3H)
1202,
611.1169
1180.
”P NMR (471 MHz. C150.) 5
1148,
-116.92 — -117.10 (111), -117.36 —
1101,
-11753(nD
1061.
1044.
911,829,
732.72(l
ation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
(Thin
3375.
2986,
1738,
1675. 1
H NMR (300 MHz. .). . -
C) 8.27 (d. .1
“01‘ :54 Hz, 1H), 8.21 (d,J:7.8 Hz, 1H),
1452’ HRMS—ESI 7.05 (td, J: 9.7, 8.2, 4.2 Hz, 4H), 6.98 —
1437’ (m z) 6.82 (m. 3H). 5.78 7 5.54 (m. 3H). 4,63 2
1366* (|M+H| ) 4.48 (m. 1H). 3.95 (d. .1: 10.1 Hz. 1H).
calcd for 3.91 (s, 3H), 2.22 (dd, J: 6.4, 2.0 Hz,
___ 1310’
127; C30H33F3N307, 6H), 2.06 (s, 3H), 1.23 (d, .1: 6.1 Hz,
1237‘ 5712250; 3H). 0.99 (d. .1: 7.2 Hz. 3H)
1262‘ found,
_ 19 A
“80’ 5712265 F NMR (471 MHz, CDC13)o
—120.03 (dt. .1: 9.7. 5.9 Hz). —120.57 (dd.
1 151’
.]:8.8.5.4 Hz)
1101,
1043.
1003. 970.
909, 828,
785, 730
‘H NMR (300 MHz. CD(‘,1~,) 8 8.27 (d. .1
: 5.4 Hz, 1H), 8.20 (d, .1: 7.8 Hz, 1H),
7.42 — 7.29 (m, 4H), 7.12 (dd, J: 8.3, 2.2
Hz. 1H). 7.08 (dd. .1: 8,3. 2.2 Hz. 1H).
HRMS-ESI 6.95 (d. .1: 5.4 Hz. 1H). 5.72 (s. 2H).
(mz) 5.70—5.58 (m, 1H), 4.58 (p,J= 7.2 Hz,
([M+H]+) 1H), 4.00 (d, .1: 9.5 Hz, 1H), 3.91 (s,
calcd for 3H). 2.07 (s. 3H). 1.26 (d. .1: 6.2 Hz.
C28H37C11N207, 3H), 1.10 (d, .1: 7.2 Hz, 3H)
643.0567;
found. 13C NMR (126 MHz. CDC1~.) 8 172.13.
643.0578 170.29. 162.96. 160.28. 145.71. 144.01.
142.25, 140.34, 133.06, 132.72, 131.62,
131.29,130.94,130.67,130.34.130.11,
127.32. 10964. 89.50. 72.10. 56.20.
5571, 48.07, 20.88, 19.07, 17.85
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
1H NMR (300 MHz, CDC13)5 8.27 (d, J
= 5.4 Hz, 1H), 8.20 (d, J: 7.8 Hz, 1H),
7.32 (td. .1: 8.3. 7.6 Hz,2H),7.11 4 6.93
(111,411), 5.72 (d,J: 0.5 Hz, 3H), 5.71 4
.60 (m, 1H), 4.67 — 4.51 (m, 1H), 4.03
((1.1: 9.3 Hz, 1H). 3.91 (s, 3H). 2.07 (s,
HREijI, 3H). 1.26 (d, .1: 6.2 Hz, 3H). 1,09 (d. .1:
7.2 Hz, 3H)
([M+H]+)
C 5111501; 0 ”C NMR (126 MHz, CD(‘,1~,)5 172.10,
’2“ 61171 13538? 7‘ 170,29, 162.95, 160.29, 158.15 (d, J:
' c1 ‘ 250.2 Hz), 158.01 (d, J: 249.8 Hz),
(131111173;f 145.70. 144.03, 142.24, 141.03 (d, .1:
’ ' ‘ 6.5 Hz), 131.08. 130.80, 124.51 (d. .1:
3.5 Hz), 124.40 (d, J: 3.6 Hz), 120.03
(d,J= 17.6 Hz), 119.73 (d,J= 17.7 Hz),
116.55 (d, .1: 21.8 Hz), 109.64. 89.51,
72.15, 56.20, 55.99, 48.05, 20.87, 19.03,
17.84
1H NMR (300 MHz. CDCL.) 8 8.80 (d. J
: 6.6 Hz. 1H). 8.49 (d. .1: 6.8 Hz. 1H).
7,58 (d, J: 66 Hz, 1H), 7.40 — 7.27 (m,
IMO‘EYSZFSI, _
4H), 7.14 — 7.01 (m, 2H), 5.67 — 5.52 (m,
1H). 4.61 4 4.46 (m. 1H). 4.18 (s. 3H).
(1191mm
410 (d, J: 99 Hz, 1H), 2,44 (s, 3H),
calcd for
223 1.27 (dd, J: 6.3, 3.1 Hz, 6H)
C27H25C11N306,
6%;23'; ”C NMR (126 MHz. CDCL.) 8 174.00,
3‘ ° ,170.13,140.79, 140.20, 133.07,
613.0468
13234, 131.62, 130.97, 130.85, 13055,
130.04, 127.30, , 108.57. 72.40,
58102, 55.48, 34.67, 18.65, 16.34
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H. ”C. 191:)
1H NMR (300 MHz. CDC13) 8 8.88 (d, J
= 6.7 Hz. 1H). 8.49 (d. J: 6.7 Hz. 1H).
7.67 (d. .1: 6.7 Hz. 1H). 7.38 4 7.28 (m.
2H). 7.09 4 6.95 (m. 4H). 5.68 4 5.49 (m.
1H), 4.59 4 4.48 (m. 1H). 4.21 (s. 3H),
4.12(d..1: 9.8 Hz. 1H). 2.44 (s. 3H).
1.31 4 1,24 (m. 6H)
HRMS-ESI
(“8171214) ”C NMR (126 MHz. CDC13) 8 174.30.
171.60. 170.11. 157.88 (61.1: 307.7 Hz).
calcd for
224 14143 (d. J: 6.1 Hz). 14087 (d. J: 6.2
C H @171: N 027 5:51 {0:22 6’ Hz),131.11. 130.71. 124.43, 123.96 (d,J
' fo11n c1 ‘
: 3.6 Hz). 120.02 (d. .1: 17.7 Hz).
$811039 119.27 (d. .1: 17.3 Hz). 116.85 (d. .1:
“ ' “ 21.3Hz).116.32(d.J=21.5Hz).
108.58. 72.61. 58.04. 55.77. 50.35. 31.59.
18.66. 16.35
19F NMR (471 MHz. CDC13) 8
-113.83 4 41 13.93 (m). 41 14.77 (t. .1: 8.7
1H NMR (300 MHz. CDC13) 8 8.27 (d, J
= 5.4 Hz. 1H). 8.13 (d. J: 7.8 Hz. 1H).
7.25 4 7.14 (m. 4H). 6.93 (dddd. .1: 18.3.
8.7. 6.6. 2.1 Hz. 5H). 5.75 4 5.61 (m.
HRMS—ESI 3H), 4.64 4 4.42 (m. 1H). 4.05 (d. J: 8.9
(m z) Hz. 1H). 3.91 (s. 3H). 2.05 (s. 3H). 1.31
(|M+Hr) (d. .1: 7.1 Hz. 3H). 1.21 (d. .1: 6.2 Hz.
calcd for 3H)
22; ___ ___
F2N2074
543.1937; ”C NMR (126 MHz. CD(‘,1~.) 8 171.93.
found, 170.30.162.76.162.66, 160.62. 160.36.
543.1949 145.64.144.15,142.26. 136.92. 136.54,
129.80. 129.74. 129.69. . 115.71.
115.54. 115.42. 115.25. 109.59. 89.62.
73.10, 56.21, 55.59. 48.03, 20.86. 18.95,
18.06
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
(Thin
3375,
33%L 1H NMR (400 MHz, CDC13) 5 6.95 —
6.77 (m, 4H), 5.57 (dq, J: 9.0, 6.2 Hz,
1:; 551? _
1H). 4.91 (d. .1: 7.8 Hz, 1H). 4.27 2 4.13
1448‘ [M+Na]+ (m, 1H), 3.93 (d, .1 : 9.0 Hz, 1H), 1.42 (s,
1,6; 9H), 1.24 (d, .1: 6.2 Hz, 3H), 1.00 (d, J:
1 d f
226 i “a C or
. 7.2 Hz, 3H)
1346,1, (,2;H2;F(,NNaO4.
3i: 3 11166113); ”F NMR (376 MHz, CDC13) 5
1165’ -132.38 (d, J: 20.6 Hz), —132.83 (d,J=
614 Mix
”1‘7‘ ‘ ' 20.6 Hz). —160.90 (t. .1: 20.5 Hz).
1094* —161.25 (t, J: 20.6 Hz)
1043, 863,
803, 786,
729, 679
(Thin
2939,
2031, 1H NMR (400 MHz, methanol-d4) o 7.36,
2 7.17 (m, 4H). 5.83 : 10.0, 6,]
1:32 HR37I7SZ)ESI? _
Hz, 1H). 4.26 (d, .1: 10.1 Hz, 1H)_ 4.00
1447’ ([M+H]+) (q, J: 7.2 Hz, 1H), 3.31 (p, J: 1.7 Hz,
3H), 1.28 (d, .1: 6.2 Hz, 3H), 1.08 (d, J:
134; Wed for
227 7‘2 HZ‘ DH)
1234, CMHMFGNOZ,
1118 ӣ33130; 19F NMR (376 MHz, methanol-d4) 5
1041’ —137.08 (d, .1: 20.0 Hz), —137.39 (5.1:
8‘72 *392 1083‘ * 19.9 Hz). —166.29 (t. .1: 19.9 Hz).
826 .802 ° -166.61 (t, J: 19.9 Hz)
752, 729,
707, 680,
666, 659
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
(Thin
33 3,
2942,
1738,
12:: ‘H NMR (400 MHz. CD(‘,1~,) 8 1 1.93 (s,
_ 1H), 8.29 (d, J: 7.9 Hz, 1H), 7.98 (d, J:
13;; “(17717531351_ 5.2 Hz. 1H), 6.94 — 6.77 (m, 5H), 5.58
{481’ (|M+H|+) (dq,.I:9.0_ 6.2 Hz. 1H).4.65 44.49 (m,
1446,,, , 1H). 3.94 (d, .1: 5.5 Hz. 4H). 1.25 (dd. .1
calcd for
228 ___ = 9 4 6 7 Hz 6H)
1344, C25H31F6N205, ' = ' 3
363 59; ”P NMR (376 MHz. CDCL) 5
1211‘ 543L112 52 —132.34 (d, J : 207 Hz), —132,74 (d, J :
3' 3
.5 Hz), -160.82 (t, J: 20.5 Hz),
1148’
1117, —161.08 (1.1: 20.5 Hz)
1094,
1040, 984,
954, 909.
849, 801.
727, 678
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C, 191:)
(Thin
3384,
2985,
1770,
1741,
1676, 1H NMR (400 MHz, CDCL) 5 8.37 (d, .1
1622, = 7.6 Hz, 1H), 8.32 (d, J: 5.4 Hz, 1H),
1592,
, 7.01(d,J= 5.5 Hz, 1H), 6.88 (dd, J:
1572, HRS/7128;“ 8.1, 6.3 Hz, 2H), 6.82 (dd, .1: 8,1, 6.2
1527, Hz, 2H), 5.56 (dq, J: 8,7, 6.2 Hz, 1H),
([M+H]+)
1447, 4.65 — 4.50 (m, 1H), 3.94 (d,J= 8.8 Hz,
calcd for
229 1368, 1H), 3.91 (s, 3H), 2.38 (s, 3H), 1.24 (d, J
(,7 HF N70
1345, [58571455 "‘ : 6.2 Hz, 3H), 1.18 (d, .1: 7.2 Hz, 3H)
1312, ' "
1237, 53111364 19F NMR (376 MHz, CDC13) 5
1199, 5 5' —132.51 (d. .1: 20.5 Hz), —132.94 (d, .1:
1176, 20.4 Hz), —161.06 (t, J: 20.5 Hz),
1117, -l61.30(t,J=20.6Hz)
1095,
1042,
1010, 954,
909, 846,
828, 803,
729, 680
ation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
MASS,
N0. (0C) (cm'l) (H, ”C. 191:)
(Thin
3384.
2987,
1743,
1675. 1
H NMR (400 MHz. CD(,1~.). -
C) 8.27 (d. .1
”79‘ :34 Hz, 1H), 8.20 (d,J: 7.7 Hz, 1H),
17,26 6.96 (d,J= 3.4 Hz, 1H), 6.90 (dd, J:
1306’ HRMS—ESI 8.2. 6.3 Hz. 2H). 6.84 (dd. .1: 8.0. 6.2
1447* (m z) Hz. 2H). 3.72 (d. .1: 1.0 Hz. 2H). 3.38
([M+H]+) (dq,J= 8.9, 6.2 Hz, 1H), 4.59 (p, J: 7.3
1366’
calcd for Hz, 1H), 3.96 (d, J: 8.8 Hz, 1H), 3.92 (s,
2,0‘ 1344’
131 szH?F?NZOz 3H). 2.07 (s. 3H). 1.26 (d. .1: 6.2 Hz.
* 1‘
* 615.1560; 3H), 1,17(d,./:7,3 Hz, 3H)
1237,
1201. fciunfl’ 19
”80 613.1370 FNMR (376 MHz. CDC];)0-
“49‘ 43249 (d. .1: 20.7 Hz). 43292 (d. .1:
1117: 20.6 Hz), -161.02 (t,J=20.6 Hz),
-161_33 (t,J=20.6Hz)
1101.
1040.
1003, 971,
911, 830,
803. 728.
ESIMS
m z 320
(11141110
1H NMR (400 MHz. CDC1~,) 5 7.21 (ddd.
.1: 11.8. 8.4. 3.2 Hz. 4H). 6.98 (td. .1:
8.6, 5.6 Hz, 4H), 5.67 (dq, J: 9.2, 6.2
Hz, 1H), 4.80 (d,J= 7.8 Hz, 1H), 4.06
ESIMS (dd. .1: 21.8. 8.4 Hz. 2H). 1.43 (s. 9H).
mz420 1.18 (dd,J: 12.5, 6.7 Hz, 6H)
([M+H]+)
13C NMR (126 MHz. CDC1~.) 5 172.42.
162.70. 162.62. 160.74. 160.67. 136.89.
136.87,129.74,129.67, , 113.76,
115.59, 113.47, 115.30, 79.79, 72.77,
55.76.419.40. 30.93.2830. 19.00. 18.30
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd.
MASS N1VJR
No, (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.25 4 7.17 (m, 1H), 7.14
(dd, J: 8.4, 5.8 Hz, 1H),
6.91 — 6.76 (m, 4H), 5.60
(dq, J: 9.8, 6.2 Hz, 1H),
(Thin ?lm) HRMS-ESI (m Z) 4.94 (d, .1: 8.0 Hz, 1H), 4.42
3367, 2979, ([M+Na]_) calcd for (d, J: 9.8 Hz, 1H), 4.12 (qd,
234 1708, 1495, F3NNaO4, J: 7.2, 2.5 Hz, 1H), 2.37 (s,
l 162, 1049, 470.21 13, found, 3H), 2.32 (s, 3H), 1.42 (s,
731 470.21 10 9H), 1.29 (d, .1: 61 Hz,
3H), 0.88 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
—116.52, -11701.
1H NMR (400 MHz, CDC13)
7.33 4 7.17 (m, 8H), 5.77
: 10.3, 6.1 Hz, 1H),
4.97 (d, J: 7.9 Hz, 1H), 4.10
(dq,J= 14.6, 7.2 Hz, 1H),
3.95 (d, .1: 103 Hz, 1H),
(Thin ?lm) HRMS-ESI (m/z) 1.41 (s, 9H), 1.26 (s, 9H),
3440, 2963, ([M+Na]_) calcd for 1.25 — 1.20 (m, 12H), 0.64
235 1708, 1365, C31H45NN304, (d, .1: 7.2 Hz, 3H).
1164, 1051, 518.3241; found,
908, 731 518.3245 13C NMR (101 MHz,
CDC13) 5 172.88, 154.92,
149.54, 149.34, 138.80,
138.25, 127.65, 127.61,
125.59, 125.29, 79.54, 73.50,
57.27, 49.13, 34.34, 34.29,
31.30,28.31,19.36, 17.73.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No. (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
6 7.244 7.17 (m, 4H), 7.164
7.05 (m, 4H), 5.76 (dq, J :
.2, 6.1 Hz, 1H), 4.97 (d, J
= 7.9 Hz, 1H), 4.09 (dq, .7:
17.8, 7.3 Hz, 1H), 3.95 (d, .1
= 10.3 Hz, 1H), 2.82 (dhept,
J: 9.4, 6.9 Hz, 2H), 1.41 (s,
HRMS-ESI (m 2) 9H), 1.22 (d, .1: 6.2 Hz,
(Thin ?lm)
]‘) calcd for 3H), 1.17 (dd,J= 11.6, 6.9
3373,2960,
236 C29H41NNaO4, Hz, 12H), 0.67 (d, J: 7.2
1711,1163,
490.2928; found, Hz, 3H).
1050, 731
490.2931
13C NMR (101 MHz,
CDC13)6172.87, 154.93,
147.27, 147.10, 139.20,
138.70, 127.91, 127.88,
126.75, 126.44, 79.54, 73.45,
57.42, 49.16, 33.64, 33.60,
28.31, 2400,2397, 23.91,
19.35, 17.79.
1HNMR (400 MHz, CDC13)
6 7.16 — 6.89 (m, 6H), 5.73
(dq,.1: 102,61 Hz, 1H),
(Thin ?lm) HRMS-ESI (m 2)
.04 — 4.90 (m, 1H), 4.19 —
3364, 2976, ([M+Na]_) calcd for
4.02 (m, 1H), 3.88 (d, J:
237 1712, 1501, C27H3-NNaO4,
.3 Hz, 1H), 2.17 :
1450, 1162, 462.2615, found,
.4, 9.0 Hz, 12H), 1141(s,
1052, 731 462.2623
9H), 1.22 (d, J: 61 Hz,
3H), 0.79 (d, .1: 7.1 Hz,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. n .
:\L \\\\\ ‘\‘\1 MP
MASS NMR
No. \'\'\x ‘ ~‘ (‘0 (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.23 (ddd, J: 16.6, 8.5, 5 ,, .3
Hz, 4H), 6.97 (td, J: 8,7,
2.2 Hz, 4H), 5.69 (dq, J =
9.1, 6.2 Hz, 1H), 4,93 (d, J
7.3 Hz, 1H), 4.08 (dd, .1:
21.8, 8.3 Hz, 2H), 1.43 (s,
9H), 1.18 (dd,J= 13.2, 6.7
Hz, 6H).
ESIMS m z 442
([M+H]+) 4R(1011V1Hz,
CDC13) 5 172.40, 162.91,
162.84, 160.46, 160.40,
154.90, 136.97, 136.94,
136.66, 129.81, 129.73,
129.69, , 129.53,
115.76,115.71,115.55,
,115.43,115.22,
79.65, 77.45, 77.13, 76.81,
72.71, 55.71, 49.44, 28.25 7
1892,1810.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd.
MASS NMR
No, (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.23 (ddd, J: 15.9, 8.7, 5.4
Hz, 4H), 6.97 (dtd, J : 8,7,
6.4, 2.1 Hz, 4H), 5.71 (dq, J
= 9.8, 6.1 Hz. 1H), 4.98 (d, J
: 7.8 Hz, 1H), 4.14 (dq,.]:
14.9, 7.6 Hz, 1H), 4.03 (d, J
= 9.8 Hz, 1H), 1.42 (s, 9H),
ESIMS m z 420 1.22 (d, J: 6.1 Hz, 3H), 0.84
([M+H]+) (d, J: 7.2 Hz, 3H).
”C NMR (101 MHz,
CDC13) 5 172.75, 162.96,
162.88, 160.51, 160.43,
154.94, 137.01, 136.97,
, 136.82, 129.58,
129.53, 129.51, 129.45,
115.80,115.59,115.49,
115.28, 79.71, 72.86, 56.20,
49.18, 28.28, 19.17, 18.02.
lH NMR (400 MHz, CDCH)
8 7.34 (dd, J: 8.6, 67 Hz,
1H), 7.12 (dd,J= 87,67
Hz, 1H), 6.64 4 6.44 (m,
4H), 5.85 (dq,J: 9.5, 6.1
(Thin ?lm) HRMS-ESI (m/Z) Hz, 1H), 4.96 (d, J = 7.8 Hz,
3355, 2978, ([M+Na]‘) calcd for 1H), 4.81 (d, J: 9.8 Hz,
240 1711, 1599, C25H31F2NN306, 1H), 4.23 4 4.02 (m, 1H),
1500, 1162, 502.2012, found, 3.82 (s, 3H), 3.74 (s, 3H),
954 502.2021 1.42 (s, 9H), 1.20 (d, J: 6.2
Hz, 3H), 0.88 (d, J: 7.2 Hz,
"’1? NMR (376 MHz, CDClg)
-113.46, -113.83.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS N1VJR
No. (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.30 - 7.13 (m, 10H), 5.83
(q, J: 6.4 Hz, 1H), 5.00 (d,
J: 5.4 Hz, 1H), 4.26 —4.12
(m, 1H), 1.73 (s, 3H), 1.41
(s, 9H), 1.15 (d, .1: 6.3 Hz,
ESIMS 777 Z 398 3H), 0.98 (d, J: 7.2 Hz,
([M+H]+) 3H).
l3(:1\11\4R(1011\4Hz,
CDC13)6172.77, 154.93,
, 145.15, 128.16,
128.10, 127.92, 127.40,
126.28, , 79.69, 75.78,
50.38, 49.39, 28.3], 23.89,
1837,1598.
1H NMR (400 MHz, CDCl;)
7.65 4 7.56 (m, 4H), 7.43 4
(Thin ?lm) 7.33 (m, 4H), 5.85 — 5.73 (m,
ESIMS mz 434
3375, 2980, 1H), 4.87 (d, J: 7.9 Hz,
242 ([M+H]+)
2934, 2229, 1H), 4. 19 (dd, .1: 9.3, 2.7
1739, 1708, Hz, 1H), 4.17 —4.01(m,
1605, 1504 1H), 1.42 (s, 9H), 1.25 (d, J
: 6.2 Hz, 3H), 0.85 (d, .7:
7.2 Hz, 3H),
1H NMR (400 MHz, CDC13)
7.56 (w: 8.1 Hz, 4H),
7.44 — 7.36 (m, 4H), 5.89 —
(Thin ?lm) ESIMS m 'z 520
N} 5.76 (m, 1H), 4.89 (d, .1: 7.8
3357, 2982, ([M+H]+)
Hz, 1H), 4.19 (d,./ : 9.8 Hz,
1709, 1617,
1H), 4.12 (t,J= 7.5 Hz, 1H),
1.41 (s, 9H), 1.26 (d, J: 6.2
Hz, 3H), 0.79 (d, .1 : 7.2 Hz,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS N1VJR
No. (cm ) (1H7 13c:1 19F)
1:1 mixture of diastereomers.
1H NMR (500 MHz, CDCl;)
7.32 4 7.23 (m, 8H), 7.22 4
7.13 (m, 2H), 5.84 — 5.72 (m,
1H), 4.93 (d, J: 7.9 Hz,
1H), 4.77 (d, .1: 6.2 Hz,
1H), 4.15 — 4.00 (m, 2H),
1.42 (s, 9H), 1.24 (d, J = 6.3
Hz, 3H), 1.22 (d, .1 : 6.0 Hz,
(Thin ?lm) HRMS-ESI(/1Iz)
3H),1.11(d,J= 7.2 Hz,
3361, 2978, +)
3H), 0.76 (d, J = 7.2 Hz,
1709, 1494,
calcd for 3H).
244 1450, 1365,
C23H30NO4,
1162, 1050,
384.2169, found, (126 MHz,
1029, 731,
384.2169 CDC13)6172.83, 172.30,
154.93, 141.50, 141.26,
128.77, 128.73, 128.49,
128.46, 128.23, ,
128.08, 128.05, 126.90,
126.87, 126.66, 79.64,
73.11, 73.03, 57.97, 57.54,
49.46, 49.17, 34.67, 28.32,
.28, 20.70, 19.30, 19.10,
18.31, 18.00.
1H NMR (400 MHz, CDC13)
7.31 (d, J: 8.2 Hz, 1H),
7.09 (d, .1: 8.1 Hz, 1H), 6.87
(dd, J: 82,20 Hz, 1H),
6.83 (dd,J= 8.1, 2.0 Hz,
(Thin ?lm) FIRMS-E81011 ”2)
1H), 6.79 (dd, .1: 14.8, 2.0
3374, 2977, ([M+Na]‘) calcd for
Hz, 2H), 5.84 (dq, J : 12.4,
245 1711,1592, C25H31C12NN306,
6.2 Hz, 1H), 4.95 (d, J: 7.3
247, 534.1421, found,
Hz,1H),4.81(d,J= 9.7 Hz,
1163,1029 534.1427
1H), 4.26 4 4.01 (m, 1H),
3.82 (s, 3H), 3.74 (s, 3H),
1.42 (s, 9H), 1.20 (d, J: 6.1
Hz, 3H), 0.89 (d, .1 : 7.2 Hz,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.30 (dd, J: 8.5, 6.8 Hz,
1H), 7.14 (dd, J: 8.5, 6.8
Hz, 1H), 6.61 — 6.43 (m,
. 4H), 5,87 (dq, J: 126, 6.3
$22)“ $912}; HRMS—ESI (m z) Hz, 1 H), 4.97 (d, .1 : 6.9 Hz,
1710’ 1598’ ([M+Na]‘) calcd for 1H), 4.80 (d, J: 10.1 Hz,
246 C27H35F2NNa06, 1H), 4.21 — 4.07 (m, 1H),
1 500’ 1274’
116010407 530.2325, found, 4.064378 (m, 4H), 1.564
9901821 7 36 ,15H),1.21(d,J=
1 6.1 Hz, 3H), 0.90 (d, J: 7.2
Hz, 3H).
191: NMR (376 MHz, CDC13)
8 -11372, -114.20.
1H NMR (400 MHz, CDC13)
7.27 (d, .1: 8.1 Hz, 1H),
7.10 (d,./: 8.2 Hz, 1H), ()84
(dd, J: 5.6, 2.6 Hz, 1H),
6'81 (dd’ J‘ 83120 HZ”
(Thin ?lm) HRMS—ESI (m z)
1H)’ 6'75 (dd’ ‘1 7
3358, 2979, ([M+Na]‘) calcd for 1449’ 2‘0
Hz, 2H), 5.86 (dq, J— 12.2,
247 1711, 1592, C27H35C12NNa06,
6.1 Hz, 1H), 4.98 (d, J— 6.9_
1491,1247, 562.1734, found,, ,
HZ 1H) 480(d 1:100
1162,1042 562.1737 ’ 1 ‘ 1‘ ‘
Hz, 1H), 4.23 — 4.07 (m,
1H), 4.07 — 3.75 (m, 4H),
1.52 41.34(m,15H), 1.21
(d, J: 6.2 Hz, 3H), 0.91 (d,
J = 7.2 Hz, 3H).
ation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS N1VJR
No, (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.25 (d, .1: 7.7 Hz, 1H),
7.12 (d, J: 7.8 Hz, 1H), 6.69
— 6.52 (m, 4H), 5.89 (dq, J:
(Thin ?lm) HRMS—ESI(I17Z) 12.3, 6.1 Hz. 1H), 5.03 (d, J
3360, 2977, ([M+Na]‘) calcd for : 6.7 Hz, 1H), 4.88 (d, .1:
248 1712, 1504, C29H41NN306, 10.2 Hz, 1H), 4.10 (q,J=
1259, 1161, 522.2826; found, 12.8, 9.8 Hz, 1H), 4.05 —
1044 52228 19 3.78 (m, 4H), 2.26 (s, 3H),
2.24 (s, 3H), 1.53 —1.33(m,
15H), 1.22 (d, J: 6.2 Hz,
3H), 0.86 (d, .1: 7.1 Hz,
1H NMR (400 MHz, CDCH)
8,02 4 7.89 (m, 4H), 7.40 4
7.29 (m, 4H), 5.89 — 5.75 (m,
1H), 4.91 (d, .1: 80 Hz,
1H), 4.35 (q,.]: 7.1 Hz,
2H), 4.34 (q, J: 7.1 Hz,
2H), 4.18 (d, J: 99 Hz,
1H), 4.16 4 4.03 (m, 1H),
1.41 (s, 9H), 1.37 (t,J= 7.1
ESIMS m z 528
Hz, 6H), 1.24 (d, J: 6.2 Hz,
249 ([M+H]+)
3H), 0.81 (d, .1: 7.2 Hz,
13C NMR (101 MHz,
CDC13) 5 172.71, 172.69,
166.18, 166.10, 145.69,
145.36, 130.18, 129.91,
129.56, 129.31, 128.25,
128.12, 72.36, 60.98, 60.95,
57.67, 2829, 19.18, 18.09,
14.29, 14.28.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. :32; MP IR NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
6.65 4 6.51 (m, 4H), 6.46
(tt, J: 10.3, 2.3 Hz, 2H),
.67 (dq,J= 10.0, 6.1 Hz,
1H)” 4'98 (d’ J: 7‘9 HZ°
(Thin ?lm) FIRMS—13810112)
- 14(dd,.1410.5,4,8
\ 3378, 2979,M ([M+Na] )calcd for
’ 1H)
3 92 ((1 J29 9H2
250 \ 1707, 1592, C25H31F2NNa06, ,1 ‘ ,1 ‘ 1
~:\ 1453, 1134, 502.2012; found, ,lH)‘ 3'76 (3’ 3H) 3‘75 (3‘
3H), 1.42(s, 9H), 1.24 (d, .1
1050 731 502 2022
1 '
= 6.2 Hz, 3H), 0.88 (d, J =
7.2 Hz, 3H).
”P NMR (3 76 MHz, CDC13)
-110.64, —111.21.
1H NMR (400 MHz, CDC13)
6 6.45 (dd, J: 4.5, 2.2 Hz,
4H), 6.28 (dt, .1: 13.7, 2.2
Hz, 2H), 5.73 (dq, .1: 10.3,
6.1 Hz, 1H), 5.00 (d, J: 7.9
Hz, 1H), 4,12(tt,J=7.1, 3.3
Hz, 1H), 3.87 (d, .1: 10.4
(Thin ?lm) HRMS-ESI (mz) Hz, 1H), 3.75 (s, 6H), 3.73
\ 3375, 2978, ([M+Na]‘) calcd for (s, 6H), 1.42 (s, 9H), 1.24 (d,
251 1708, 1593, C27H37NNan, .l: 6.1 Hz, 3H), 0.84 (d, .1:
1456, 1149, 526.2411; found, 72 Hz, 3H).
1059, 729 526.2409
13C NMR (101 MHz,
CDCl;,) 6 172.84, ,
160.78, 154.94, 143.51,
143.22, 106.45, 106.20,
98.58, 98.44, 79.63, 72.69,
58.27, 55.28, 55.26, 49.25,
28.31, 19.27, 18.07.
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H,1”C,19F)
1H NMR (400 MHz, CDC13)
6.69 (s, 2H), 6.66 4 6.62
(m, 2H), 6.54 (s, 1H), ()50
(s, 1H), 5.72 (dq, J: 10.4,
6.1 Hz, 1H), 5.00 (d, .1: 7.9
Hz, 1H), 4.22 4 4.00 (m,
1H), 3.86 (d, J: 10.4 Hz,
1H), 3.74 (s, 3H), 3.73 (s,
(Thin ?lm) 3H), 2.28 (s, 3H), 2.25 (s,
HRMS-ESI(/1Iz)
3370, 2978,
9'5;1(9/ 3H), 1.41 (s, 9H), 1.22 (d, J
([M+Na]_) calcd for
1708, 1594, = 6.2 Hz, 3H), 0.80 (d, J:
1454, 1292, C27H3115Na06’ 7.1 Hz, 3H).
in: 494.2513; found,
1155,1051,4
494 2510 1
729 ' 1"CN1\/IR(1011\4HZ,
CDC13)6172.85, 159.78,
159.65, , 142.79,
142.49, 139.72, ,
121.29, 112.72, 112.69,
111.34, 110.84, 79.59, 72.99,
57.93, 55.12, 55.11, 49.24,
2832,2165, 2158,1931,
18.02.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H. 13C. 191:)
1H NMR (400 MHz. CDC13)
7.00 (ddd. .1: 13.3. 7.6. 0.9
Hz. 2H). 6.85 i 6.68 (m.
4H). 5.78 (dq. J: 10.3. 6.1
Hz, 1H). 5.11 —4.82 (m.
1H).4.12(qd..1:7.1.2.3
Hz. 1H). 3.94 (d. J: 10.2
Hz. 1H). 3.79 (s. 3H). 3.78
' 2 (5‘
(Thin ?lm) SI (m z) (3’ "1112”“ 3H)” 2‘
. 3H).1.41(s.9H).124(d.J
3377. 2978. ([M+Na] for
:61Hz 3H) 080(d J:
253 1711.1508. C27H3+NNa06. ' 712mm) ’
1252.1163. 4942513150115. ‘ ’ ‘
1041. 732 494.2493
13CN1\4R(1011V1Hz.
CDC13)6172.87. 157.86.
157.65. 154.93. 140.45.
140.25. . 130.47.
125.22. 124.79. 119.74.
119.69. 109.82. 109.77.
79.64. 73.09. 57.95. 55.27.
55.25. 49.29. 28.32. 19.35.
18.06. 15.80. 15.75.
1H NMR (400 MHz. CDC13)
7.06 i 6.92 (m. 4H). 6.88
(td. J: 817. 4.6 Hz. 2H).
.63 (dq. J: 9.6. 6.2 Hz.
1H). 4.99 (d. .1: 7.9 Hz.
(Thin ?lm) HRMS-ESI (/77 Z)
1H). 4.13 (p.J: 6.9 Hz.
3377. 2979, ([M+Na]7) calcd for
1H). 3.91 (d..]= 9.6 Hz.
254 1706. 1513. C25H31F2NNa06,
1H). 3.84 (s. 3H). 3.83 (s.
1274. 1161. 502.2012; found,
3H). 1.42 (s. 9H). 1.22 (d, J
1025. 729 502.2008
= 6.2 Hz. 3H). 0.90 (d, J:
7.2 Hz. 3H).
19F NMR (376 MHz. CDC13)
—134.14.—134.59.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.05 (ddd, .7: 7,8, 4.8, 2.3
Hz, 2H), 7.01 (d, J : 2.2 Hz,
2H), 0.70 (t, J: 8.8 Hz, 2H),
.08 (dq, .1: 10,1, 0.1 Hz,
1H), 4.98 (d, .1: 7.9 Hz,
1H), 4.12 (ddp, J: 11.8, 7.9,
4.3 Hz, 1H), 3.85 (d,J= 10.2
Hz, 1H), 3.70 (s, 3H), 3.74
(Thin ?lm) HRMS-ESI (m z) (s, 3H), 2,16 (s, 3H), 2.14 (s,
3370, 2978, ([M+Na]_) calcd for 3H), 1.41 (s, 9H), 1.21 (d, J
255 171 1, 1502, C27H37NNaOG, : 0.1 Hz, 3H), 0.82 (d, .7:
1247, 1103, 494.2513, found, 72 Hz, 3H).
1052, 730 494.2515
13CNMR(101 MHz,
CDC13) 5 172.87, 150.53,
150.30, 154.94, 133.77,
133.55, 130.40, 130.30,
126.81, 120.38, 120.00,
125.80, 110.05, ,
79.58, 73,47, 5031, 55.32,
55.27, 49.28, 28.32, 19.34,
18.15, 10.32, 10.24.
1H NMR (400 MHz, CDC13)
7.04 (d, J: 3.0 Hz, 1H),
0.80 (d, J: 3.0 Hz, 1H), 0.74
(dd, .1: 19.1, 8.9 Hz, 2H),
(Thin ?lm) HRMS-ESI(/1Iz) 0.00 (ddd, J: 9.1, 0,3, 3.0
3355,2978, ([M+Na]_) calcd for Hz, 2H), 5.88 (dq, J = 10.0,
256 1712, 1497, NN308, 0.2 Hz, 1H), 5.03 (d, .1: 7.8
161, 526.241 1, found, Hz, 1H), 4.91 (d, J: 10.1
1047, 730 526.2405 Hz, 1H), 4.12 (m, 1H), 3.80
(s, 3H), 3.73 (s, 3H), 3.71 (s,
3H), 3.70 (s, 3H), 1.41 (s,
9H), 1.30— 1.19 (m, 3H),
0.80 (d, J = 7.2 Hz, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd.
MASS N1VJR
No. (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.05 (d, .1: 8.4 Hz, 1H),
6.99 (d, J: 8.3 Hz, 1H), 6.88
(d,J= 2.7 Hz, 1H), 6.81 (d,
.1: 2.7 Hz, 1H), 6.63 (ddd, J
(Thin ?lm) HRMS-ESI (m 2)
: 15.9, 8.3, 2.7 Hz, 2H), 5.63
.m...,;4€;// 3364, 2978, ([M+Na]‘) calcd for
(dq,J= 10.0, 6.1 Hz, 1H),
257 ”4., 1710, 1497, C27H3‘NNaO6»
4.99 (d, J: 7.9 Hz, 1H), 4.43
1245, 1160, 494.2513; found,
(d, .1: 10.1 Hz, 1H), 3.72 (s,
1045, 730 494.2507
3H), 3.72 (s, 3H), 2.32 (s,
3H), 2.26 (s, 3H), 1.46 4
l.39(m, 10H), 1.30(d, .1:
6.2 Hz, 3H), 0.86 (d, J: 7.2
Hz, 3H).
1H NMR (400 MHz, CDC13)
7.08 4 6.91 (m, 3H), 6.89 4
6.82 (m, 1H), 6.76 (ddd, J:
8.0, 3.8, 1.7 Hz, 2H), 5.76 4
.53 (m, 1H), 5.15 4 5.07 (m,
1H), 5.07 4 4.93 (m, 1H),
4.21 4 4.03 (m, 1H), 3.90 4
3.80 (m, 9H), 3.76 4 3.72 (m,
3H), 1.47 —1.37(m,9H),
HRMS-ESI (m z)
1.24 (t, .1: 6.0 Hz, 3H), 1.14
([M+H]+)
(61.1: 6.9 Hz, 1H), 0.86 (d,
calcd for J = 7.0 Hz, 2H).
C27H37N08Na,
526.241 1, found, 13C NMR (101 MHz,
526.2405 CDC13)6172.73, 172.19,
152.83, 152.74, 147.49,
147.21, 135.15, 135.02,
134.77, 134.64, 123.63,
123.58, , 120.98,
120.94, 120.51, 120.38,
110.86, , 110.67,
73.58, 60.35, 60.29, 60.20,
55.65, 42.03, 41.98, 28.31,
18.90,18.77,18.52,18.19.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
CmNE.d. \ MP 1R NMR
(0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.09 4 7.02 (m, 1H), 6.88 4
.74 (m, 3H), 5.70 4 5.59 (m,
1H), 4.95 (d, J: 7.9 Hz,
1H), 4.85 (d, J: 9.7 Hz,
1H), 4.22 4 4.07 (m, 1H),
3.97 (d, J: 2.4 Hz, 3H), 3.86
(d, J: 2.1 Hz, 3H), 1.42 (s,
. - 9H), 1.23 (d, .1: 6.2 Hz,
SEE“ $191311) 3H), 0.96 (d, J: 7.2 Hz,
,7 ’ HRMS-ESI (mz) 3H).
1715,1618, -
([M+Na] )calcd for.
\ 1501 1475 12
259 :4: 1430’ 1293’ F4N06Na, ”C NMR (126 MHz,
1252’ 1165’ 23; found, CDC13)5172.67, 154.91,
1102:1058: 538.1826 151.50, 151.26 (11.5113
Hz), 149.47 (Gui 11.5 Hz),
951’ 748
149.28 (d, J: 11.5 Hz),
147.24, , 147.03,
146.97, 145.35, 145.24,
143.36, 143.25, 129.90 (d,J
=35 Hz), 129.59, 123.09—
122.78 (111), 122.38, 110.96
— 110.60 (m), 79.81, 72.19,
61.23, 61.17, 49.21, 42.46,
28.29, 18.87, 18.29.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
CmNE.d. \\ MP IR NMR
(0C) (cm'l) (1H,13C,19F)
1H NMR (400 MHz, CDC13)
7.07 4 6.84 (m, 6H), 5.64
(dq,J: 11.9, 5.9 Hz, 1H),
4.96 (d, J: 8.1 Hz, 1H), 4.44
(d, J: 10.3 Hz, 1H), 4.18 —
4.02 (m, 1H), 2.35 (s, 3H),
. 2.29 (s, 3H), 2.27 (s, 3H),
3382, 2977),Thm ?lm 2‘25 (3’ 1H) 1‘42 ES” 9H)”a
HRMS—ESI (m z)
- 1.27 (d, .14 6.1 Hz, 3H), 0.82
2950, 1715,, ([M+Na] )calcd for
\ (d J: 7 2H2 3H)
260 1501, 1453, NO4Na, ’ ' ’ '
167131;365 9 4624253381?“d°~. 2222212221222
* ’ '
, CDC13) 5 172.97, 154.93,
811, 754
, 138.55, 135.43,
135.04, 133.58, 133.35,
130.57, 130.28, 128.58,
127.87, 127.22, 126.90,
79.67, 7472, 4926, 47.36,
34.67, 28.32, 21.26, 21.22,
19.77, 19.73, 18.86.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (H, 13C, 19F)
1H NMR (400 MHz, CDC13)
7.15 (d, .1: 8.5 Hz, 1H),
7.11 (d, J: 8.5 Hz, 1H), 6.96
— 6.88 (m, 4H), 5.64 (dq, J:
9.9, 6.1 Hz, 1H), 4.94 (d, J:
7.9 Hz, 1H), 4.42 (d, .1: 10.0
Hz, 1H), 4.17 — 4.05 (m,
1H), 2.34 (s, 3H), 2.30 (3,
(Thin ?lm) 3H), 2.25 (s, 3H), 2.22 (s,
3364, 2977, ([IMHfN‘li?i$21};r 3H), 1.42 (s, 9H), 1.28 (d, J
1713,1499, =62 Hz, 3H), 0.84 (d,J=
26 1 1“: C27H}7N04Na,
1452, 1365,,, 7.1 Hz, 3H).,, :2:
:1: 462.261 5, found,
1209,1164,
462 2614 1
1049, 731 ' 13C NMR (126 MHz,
6172.88, 154.95,
136.54, 136.39, 136.19,
136.07, 135.85, 135.52,
131.49, 131.16, ,
127.12, 126.82, 126.56,
79.63, 74.68, 49.24, 46.84,
34.67, 31.59, 2832, 20.84,
.10, 20.06, 18.94.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No, (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
6 7.11 (dd, .1: 8.4, 6.0 Hz,
1H), 7.07 (dd, J: 8.5, 60
Hz, 1H), 7.00 (dd, J: 10.6,
2.6 Hz, 1H), 6.90 (dd, J:
.3, 2.7 Hz, 1H), 6.87 4
6.77 (m, 2H), 5.55 (dq,J=
9.6, 6.2 Hz, 1H), 4.95 (d, J:
7.2 Hz, 1H), 4.45 (dt, .1:
9.6, 1.2 Hz, 1H), 4.20 — 4.08
(m, 1H), 2.34 (s, 3H), 2.28
(Thin ?lm)
(s, 3H), 1.42 (s, 9H), 1.31 (d,
3381,2979,
HRMS-ESI(I1IZ) J: 6.2 Hz, 3H), 0.89 (d,J:
1711,1609,
([M+Na]_) calcd for 7.3 Hz, 3H).
1589,1495,
262 C25H31F2NO4N3,
1454,1300,
4702113, found, 1\4R(1261\4Hz,
1241,1165,
470.2120 CDC13) 5 172.77, 161.36 (d,
1049, 810,
.1: 2439 Hz), 16132 (d, .1:
2435 Hz), 154,96, 14069
(d, J: 6.7 Hz), 14010 (d, J
= 6.4 Hz), 132.38 (d,J= 3.2
Hz), 132.07, 132.01, 131.69
(d,J= 7.9 Hz), 114.83 (d,J
=22.3 Hz), 114.34 (d,J=
22.2 Hz), 11307 (d, .1: 20.7
Hz), 113.35 (d,J= 207 Hz),
7979, 73.85, 49.16, 47.74,
34.67, 31.59, 28.31, 19.39,
19.35, 18.82, 18.05.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.01 4 6.86 (m, 3H), 6.82
(dd, J: 5.8, 3.1 Hz, 1H),
6.74 — 6.64 (m, 2H), 5.82
(dq,J= 12.0, 6.2 Hz, 1H),
4.97 (d, .1: 7.8 Hz, 1H), 4.67
(d, J: 10.5 Hz, 1H), 4.21 —
4.09 (m, 1H), 3.74 (s, 6H),
1.42 (s, 9H), 1.29 (d, .1: 6.2
(Thin ?lm) Hz, 3H), 0.89 (d, J = 7.3 Hz,
2978, 1710, HRMS-ESI (mt) 3H).
1497, 1454, ]‘) calcd for
263 1366, 1249, C25H31F2N06, 13C NMR (126 MHz,
1209, 1160, 502.2012, found, CDC13) 5 172.70, 156.13,
1036, 814, 11 155.90, 155.74, 155.57,
728 154.90, 154.24, 154.00,
127.94 (d,J= 15.8 Hz),
12763 (d, J: 16.2 Hz),
11624 (d, J: 24.9 Hz),
115.97 (d,J=24.8 Hz),
115.14, 114.12, 1]3.16(d,J
: 8.3 Hz), 113.03 (d, .1: 8.2
Hz), 79.69, 71.79, 55.70,
49.15, 43.38, 34.66, 28.30,
19.00, 18.12.
ation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
CmNE,d. MP 1R NMR
(0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.27 (1, .1: 8.6 Hz, 1H),
7.16 (t, J: 8.5 Hz, 1H), 6.65
— 6.50 (m, 4H), 5.82 — 5.72
(m, 1H), 4.96 (d, J: 7.9 Hz,
1H), 4.60 (d, .1: 10.2 Hz,
1H), 4.21 — 4.09 (m, 1H),
3.75 (s, 3H), 3.74 (s, 3H),
1.42 (s, 9H), 1.26 (d, .1: 6.1
297181 $191316). -
Hz, 3H), 0.92 (d, J = 7.3 Hz,
1 ,’ HRMS-ESI (m’Z) 3H).
1712, 1623, -
([M+Na] )calcd for.
1585 1506 12
264 C25H31F2N06Na, ”C NMR (126 MHz,
1 44 51 1366’
1288’ 1159’ 502.2012, found, CDC13) 5 172.73, 161.24 (d,
1031”, 950’” 502.2016 .1: 2457 Hz), 16101 (d, .1:
246.0 Hz), 15975 (d, J:
8347 731
11.1 Hz), 159.50 (d,J= 11.3
Hz), 154.93, 129.86 (61.1:
.8 Hz), 129.31, 119.70 (d,J
= 14.6 Hz), 119.41 (d,J=
.1 Hz), 110.15 (d, .1=2.9
Hz), 109.77 (d, .1: 3.0 Hz),
101.81 (d,J= 26.8 Hz),
79.67, 72.07, 55.51, 49.19,
41.73, 28.31, 19.01, 18.24.
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.53 (d, .1: 8.0 Hz, 1H),
7.31 (d, J: 8.0 Hz, 1H), 7.16
(d, J: 7.6 Hz, 1H), 7.14 —
7.10(m, 1H), 7.01 (dd, J:
.7, 1.7 Hz, 2H), 6.01 4
.91 (m, 1H), 4.97 (d, J: 9.7
Hz, 1H), 4.93 (d, J: 8.0 Hz,
(Thin ?lm) 1H), 4.18 4 4.06 (m, 1H),
2982, 1714, 3.89 (s, 3H), 3.81 (s, 3H),
1507, 1456, “$3?ng212m 141 (s, 9H), 1.23 (d, J: 6.2
1417, 1327, Hz, 3H), 0.83 (d, .1: 7.2 Hz,
1243, 1212,,,
F0N00Na, ,,
, 3H).
602.1948, found,
1166, 1123,
6021948 q
1033, 860, ‘ 13C NMR (126 MHz,
739 CDC13) 5 172.77, 157.43,
154.92, 132.51, 132.36,
130.03, 129.43, 125.01,
122.84, 117.27 (q, J: 3.9
Hz), 116.99 (q, J: 3.3 Hz),
107,64(q,J=3.0Hz),
107.44 ((1, .1: 4.1 Hz),
79.75, 7176, 55.70, 49.17,
28.29, 18.94, 18.11.
v) 0 La)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd.
MASS N1VJR
No, (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.39 (dd, J: 8.7, 5.6 Hz,
1H), 7.27 4 7,22 (m, 1H),
7.16 4 7.05 (m, 2H), 6.98 4
6.89 (m, 2H), 5.58 (dq,J=
88,62 Hz, 1H), 4.95 (d, .1:
7.4 Hz, 1H), 4.68 (d, J: 9.1
(Thin ?lm) HRMS-ESI (m/z)
Hz, 1H), 4.61 (d, J: 12.4
3355, 2961, ([M+Na]_) calcd for
Hz, 1H), 4.53 (d, .1: 12.5
266 1712, 1493, C27H35F2N06Na»
Hz, 1H), 4.42 (d, J: 12.3
1366, 1266, 530.2325; found,
Hz, 2H), 4.18 4 4.06 (m,
1160, 1095 31
1H), 3.42 (s, 3H), 3.41 (s,
3H), 1.42 (s, 9H), 1.27 (d, J
= 6.2 Hz, 3H), 0.90 (d, J:
7.2 Hz, 3H).
19F NMR(376 MHz, CDC13)
4115.52, —11588.
1H NMR (400 MHz, CDC13)
7.40 (dd, J: 87,56 Hz,
1H), 7.24 (dd, .1: 8.7, 5.6
Hz, 1H), 7.13 (t, J: 3.2 Hz,
1H), 7.10 (t, J: 3.2 Hz, 1H),
6.96 4 6.88 (m, 2H), 5.59
(dq, J: 8.7, 6.2 Hz, 1H),
4.98 (d, J: 7.5 Hz, 1H), 4.69
(Thin ?lm) HRMS-ESI (m z)
(d, J: 89 Hz, 1H), 4.65 (d,
3356, 2977, ([M+Na]‘) calcd for
J: 12.5 Hz, 1H), 4.59 (d,J:
267 1712, 1494, C29H39F2N06Na,
12.6 Hz, 1H), 4.46 (d, J:
1366, 1160, 558.2638; found,
12.5 Hz, 1H), 4.45 (d, .1:
1 1 16, 1096 558.2638
12.6 Hz, 1H), 4.20 4 4.06
(m, 1H), 3.62 4 3.44 (m,
4H), 1.42 (s, 9H), 1.32 4
1.18 (m, 9H), 0.91 (d, .1: 7.2
Hz, 3H).
”P NMR (376 MHz, CDCH)
-115,64,-115.97.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.07 (q, .1: 8.0 Hz, 4H),
6.93 (dd, J: 7.7, 3.2 Hz,
(Thin ?lm) 2H), 6.85 (t, J = 7.5 Hz, 2H),
3372,2978, 6.74 — 6.62 (m, 4H), 5.65
2936, 2835, HRMEESU’" ‘) (dqd, J : 9.3, 6.1, 3.1 Hz,
([ 1 )
1713, 1582, 2H), 4.96 (d, J: 7.4 Hz,
1500, 1457, calcd for 1H), 4.81 (s, 1H), 4.60 (dd, J
1366, 1306, C27H37N06Na, : 9.9, 6.0 Hz, 2H), 4.09 (dt,
1257, 1211, 494.2513, found, J: 15.3, 6.9 Hz, 2H), 3.79
1166, 1098, 494.2490 (3, 6H), 3.77 (s, 3H), 3.76 (s,
1048, 910, 3H), 2,27 (d, .1: 7.5 Hz,
752, 734 6H), 2.20 (s, 6H), 1.43 (s,
9H), 1.42 — 1.38 (m, 12H),
1.26 (1, .1: 6.0 Hz, 6H), 0.83
(d, J: 7.2 Hz, 3H).
1H NMR (400 MHz, CDCl;)
8 7.30 (dd, .1: 7.6, 1.4 Hz,
. 2H), 7.14 (d,J= 7.7 Hz,
52117“ $17118) 2H), 7,11 — 6.99 (m, 4H),
[712’ 1500’ HRMS—ESI (m z) 6.99 4 6.87 (m, 4H), 5.73 4
’ ’ ([M+H]+) 5.49 (m, 2H), 5.20 (d, J = 7.3
1467, 1452,
1420, 1565,4
Hz, 1H), 5.14 — 4.98 (m,
A; calcd for
269 5 a
:2 3H), 4.1 1 (s, 2H), 3.81 (8,
$51 1250, 1207, N00Na,
“E ,, ,, ,, ,,
, 3H), 3.76 (S, 3H), 3.74 (S,
1162, 1091, 494.2513, found, , ,
1053, 1006,,
3H),).71(s,5H),2.35 —
4942509
2.23 (m, 12H), 1.43 (d, .14, , i
909 866
12.5 Hz, 18H), 1.26(dd,J:
7657 730
6.2, 2.1 Hz, 6H), 1.09 (d,J=
6.8 Hz, 3H), 0.82 (d, .1: 7.1
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. MP 1R NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.31 (d, .1: 8.5 Hz, 1H),
7.11 (d, J: 8.4 Hz, 1H), 6.41
(dt, J = 5.2, 2.6 Hz, 2H),
$221 $17116). 6.37 (dt, .1 = 5.6, 2.7 Hz,
2H)” 5 '84 “1‘17 J :3‘8’ 6‘2
2935, 2836, ESIMS m z 521
([M+NH4]+) Hz, 1H), 5.01 (d, J— 7.9 Hz,
1711 1608
1585’1504’ 1H), 4.79 (d,.]= 9.9Hz,
‘ 1453 ’ 1H), 41844.06 (m, 1H),
3.81 (s, 3H), 3.74 (s, 6H),
3.73 (s, 3H), 1.42 (s, 9H),
1.20 (d, .1: 6.2 Hz, 3H), 0.88
(d, J : 7.2 Hz, 3H).
1H NMR (300 MHz, CDCH)
7,28 (d, J: 7.8 Hz, 1H),
7.13 — 7.03 (m, 1H), 6.69 —
. 6.56 (m, 4H), 5.86 (dq, J:
S??? $91217) 9.8, 6.2 Hz, 1H), 5.01 (d, J :
271 334’ 1712’ ESIMS m z 489 7.8 Hz, 1H), 4.88 (d, J = 9.9
’ ’ ([M+NH4]+) Hz, 1H), 4.20 — 3.98 (m,
1611,1504,
1H), 3.81, (S, 3H), 3.7.)a 4 3 (S,
3H), 2.27 (s, 3H), 2,26 (s,
3H), 1.41 (s, 9H), 1.21(d,J
: 6.1 Hz, 3H), 0.85 (d, J:
71 Hz, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd.
MASS NMR
No. (cm ) (1H7 13c:1 19F)
1H NMR (300 MHz, CDC13)
7.18 (d, .1: 2.1 Hz, 1H),
7.03 (d, .7: 2.2 Hz, 1H), 6.95
— 6.88 (m, 2H), 6.73 (d, J:
8.3 Hz, 1H), 6.68 (d, .1: 8.3
(Thin ?lm) Hz, 1H), 5.83 (dq, .7: 12.2,
3366, 2978, 6.1 Hz, 1H), 5.03 (d, J: 7.9
ESIMS m z 489
272 2933, 2835, ([M+NH4]+) Hz, 1H), 4.93 (d, J: 10.3
1714, 1501, Hz, 1H), 4.19 4 4.05 (m,
1453 1H), 3.81 (s, 3H), 3.72 (s,
3H), 2.24 (s, 3H), 2.21 (s,
3H), 1,42 (d, .1: 0.6 Hz,
9H), 1.21 (61,7: 61 Hz,
3H), 0.84 (d, J: 7.2 Hz,
1H NMR (400 MHz, CDC13)
7.05 - 6.93 (m, 2H), 6.91 -
6.75 (m, 4H), 5.71 (dq,./:
.1, 6.2 Hz, 1H), 4.91 (d, J
= 7.9 Hz, 1H), 4,20
- 4.07
ESIMS 777 Z 480
(m, 1H), 3.96 (d, .7: 10.0
([M+H]+)
Hz, 1H), 3.86 (s, 3H), 3.85
(s, 3H), 1.42 (s, 9H), 1.23 (d,
.7: 6.1 Hz, 3H), 0.86 (d, .1:
7.2 Hz, 3H),
19F NMR (376 MHz, CDC13)
-13712, -13769,
1H NMR (400 MHz, CDC/17,)
7.22 _ 7.04 (m, 2H), 6.77 _
6.56 (m, 4H), 5.60 (dq, J =
9.8, 6.1 Hz, 1H), 4,95 (d,J=
ESIMS m z 472
7.9 Hz, 1H), 4.36 (d, .1: 10.0
274 ([M+H]+)
Hz, 1H), 4.20 — 4.03 (m, 1H),
3.75 (s, 3H), 3.73 (s, 3H),
2.35 (s, 3H), 2.31 (s, 3H),
1.42 (s, 9H), 1.27 (d, J: 6.2
Hz, 3H), 0.87 (d, J: 7.2 Hz,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd.
No1 (cm ) (1H, 13C, 191:)
ESIMS m z 432
275 ([M+H]+)
1H NMR (400 MHz, CDC13)
7.35 _ 7.28 (m. 2H), 7.25 _
7.20 (m. 2H), 7.20 — 7.09 (m.
2H). 6.65 _ 6.51 (m, 2H),
.81 (dq. .1: 10.0. 6.2 Hz.
ESIMS 771 Z 432 1H). 4.92 (d, J: 8.0 Hz,
276 ([M+H]+) 1H). 4.53 (d, J: 10.1 Hz.
1H). 4.19 _ 4.04 (m. 1H),
3.83 (s. 3H), 1.42 (s, 9H).
1.23 (d. J: 6.2 Hz. 3H), 0.78
(d, .1: 7.2 Hz. 3H).
19F NMR (376 MHz. CDC13)
a -11326.
1H NMR (400 MHz. CDC13)
8 7.33 - 7.20 (m, 5H). 7.19 —
7.10 (m. 1H). 6.92 - 6.81 (m.
2H), 5.75 (dq, J: 10.3, 6.1
Hz. 1H). 4.91 (d. J: 8.0 Hz.
ESIMS 777 Z 416
1H), 4.26 (d, .1: 10.3 Hz,
277 ([M+H]+)
1H). 4.18 - 4.02 (m, 1H),
2.38 (s. 3H), 1.42 (s, 9H).
1.25 (d, .1: 6.1 Hz. 3H). 0.79
(d. J: 7.2 Hz. 3H).
19F NMR (3 76 MHz. CDClg)
-11670.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS NMR
No. (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz. CDC13)
7.32 - 7.12 (m. 6H). 6.59
(td. J: 5.3. 2.6 Hz. 1H).
6.52 (dd. J: 10.9. 2.5 Hz.
1H). 5.79(dq..1= 10.1. 6.1
ESIMS m z 432 Hz. 1H). 5.00 (d. .1: 8.2 Hz.
278 ([M+H]+) 1H). 4.51 (d, J: 10.2 Hz.
1H). 4.19 — 4.04 (m. 1H).
3.75 (s. 3H). 1.41 ).
1.21 (d. J: 6.1 Hz. 3H), 0.86
(d. J: 7.2 Hz. 3H).
”P NMR (376 MHz. CDC13)
—113.59.
1H NMR (400 MHz. CDC13)
7.35 — 7.15 (m. 6H). 6.90 —
6.77 (m. 2H). 5.72 (dq. J:
.1. 6.1 Hz. 1H). 4.97 (d. .1
= 8.4 Hz. 1H). 4.23 (d, J =
ESIMS m z 416
.1 Hz. 1H). 4.19 — 4.03 (m.
279 ([M+H]+)
1H). 2.31 (s. 3H). 1.42 (s.
9H). 1.23 (d. J: 6.1 Hz.
3H). 0.82 (d. J: 7.2 Hz.
19F NMR (376 MHz. CDC13)
-117.14_
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS NMR
No. (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.19 (d, .1: 8.0 Hz, 2H),
7,13 (51,1: 8.1, 6.5 Hz,
1H), 7.04 (d, J: 7.9 Hz,
2H), 6.61 _ 6.50 (m, 2H).
.78 (dq, .1: 9.7, 6.1 Hz,
ESIMS m z 446
1H), 4.94 (d, J: 7.8 Hz,
280 ([M+H]+)
1H), 4.49 (d, J: 9.8 Hz,
1H), 3.82 (s, 3H), 2.26 (s,
3H), 1.42 (s, 9H), 1.21 (d, J
= 6.2 Hz, 3H), 0.82 (d, J:
7.2 Hz, 3H).
19F NMR (376 MHz, CDC13)
-11347.
1H NMR (400 MHz, CDC13)
7.31 - 7.25 (m, 1H), 7.16 -
7.09 (m, 2H), 7.04 (d, .1: 7.8
Hz, 2H), 6.91 _ 6.80 (m, 2H),
.72(dq,J= 102,62 Hz,
1H), 4.92 (d, .1: 8.0 Hz,
ESIMS m z 430
1H), 4.22 (d, J: 10.2 Hz,
281 ([M+H]+)
1H), 4.18 — 4.02 (m, 1H),
2.37 (s, 3H), 2.25 (s, 3H),
1.42 (s, 9H), 1.24 (d, J: 6.1
Hz, 3H), 0.83 (d, .1: 7.2 Hz,
19F NMR (376 MHz, CDC13)
-116.91.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd.
MASS NMR
No. (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.26 (dd, .7: 8.5, 6.5 Hz,
1H), 7.16 (d,J: 8.1 Hz,
2H), 7.06 (d, J: 8.0 Hz,
2H), 6.58 (td, .1: 83,26
Hz, 1H), 6.52 (dd, .1: 10.9,
2.5 Hz, 1H), 5.77 (dq,J=
ESIMS m z 446
.1, 6.1 Hz, 1H), 5.01 (d,J
282 ([M+H]+) : 8.4 Hz, 1H), 4.48 (d, .1:
.3 Hz, 1H), 4.19 — 4.04 (m,
1H), 3.76 (s, 3H), 2.27 (s,
3H), 1.41 (s, 9H), 1.21 (d, .1
: 6.1 Hz, 3H), 0.85 (d, J:
7.2 Hz, 3H).
"’F NMR(376 MHz, CDC13)
-113.81.
'H NMR (400 MHz, CDCH)
7.31 (dd, J: 8.6, 5.8 Hz,
1H), 7.14 — 7.04 (m, 4H),
6.87 — 6.77 (m, 2H), 5.70
(dq,J= 10.1, 6.1 Hz, 1H),
ESIMS m 'z 430 4.97 (d, J: 7.8 Hz, 1H), 4.19
([M+H]+) (d,./: 10.3 Hz, 1H),4.17—
4.02 (m, 1H), 2.31 (s, 3H),
2.28 (s, 3H), 1.42 (s, 9H),
1.22 (d, .1: 6.2 Hz, 3H), 0.81
(d, J: 7.2 Hz, 3H).
19F NMR (376 MHz, CDCH)
-11735.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS NMR
No, (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8 7.35 - 7.22 (m, 2H), 7.12
(dd, J: 84,65 Hz, 1H),
6.98 — 6.84 (m, 2H), 6.71 —
6.48 (m, 2H), 5.78 (dq, J:
12.1, 6.3 Hz, 1H), 4.91 (d, .1
ESIMS m z 450
= 8.0 Hz, 1H), 4.49 (d, J:
284 ([M+H]+) 9.9 Hz, 1H), 4.25 — 4.02 (m,
1H), 3.82 (s, 3H), 1.42 (s,
9H), 1.22 (d, J: 6.2 Hz,
3H), 0.84 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
8 —112.92, —116.53.
1H NMR (400 MHz, CDC13)
8 7.31 - 7.16 (m, 3H), 7.00 -
6.79 (m, 4H), 5.70 (dq, .1:
.3, 6.1 Hz, 1H), 4.89 (s,
ESIMS m z 434 1H), 4,25 (d, J: 10.2 Hz,
285 // ([M+H]+) 1H), 4.18 _ 4.04 (m, 1H),
2.36 (s, 3H), 1.42 (s, 9H),
1.25 (d, J: 6.1 Hz, 3H), 0.87
(d, .1: 7.0 Hz, 3H).
19F NMR (376 MHz, CDC13)
8 —1]6.06, —116.38.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS NMR
No. (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.25 - 7.19 (m, 3H), 6.99 -
6.90 (m, 2H), 6.60 (td, J:
8.3, 2.5 Hz, 1H), 6.54 (dd, J
= 10.9, 2.5 Hz, 1H), 5.74
(dq,.1: 11.9, 6.1 Hz, 1H),
ESIMS m z 450
4.94 (d, J: 7.8 Hz, 1H), 4.48
286 ([M+H]+)
(d,J= 10.2 Hz, 1H), 4.19 —
4.05 (m, 1H), 3.77 (s, 3H),
1.42 (s, 9H), 1.20 (d, J: 6.2
Hz, 3H), 0.86 (d, J: 7.3 Hz,
19F NMR (376 MHz, CDC13)
8 -113.32, —116.1 1.
1H NMR (400 MHz, CDC13)
7.30 (dd, J: 8,6, 5.7 Hz,
1H), 7.24 _ 7.11 (m, 2H),
7.01 — 6.93 (m, 2H), 6.92 —
6.69 (m, 2H), 5.67 (dq, J:
.0, 6.2 Hz, 1H), 4.92 (d, .1
ESIMS m z 434
= 6.4 Hz, 1H), 4.22 (d, J:
287 ([M+H]+) 10.0 Hz, 1H), 4.18 — 401(m,
1H), 2.29 (s, 3H), 1.42 (s,
9H), 1.22 (d, J: 6.2 Hz,
3H), 0.83 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
6 -11553, -11686.
v) La)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No. (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.21 (dd, .1: 8.5, 6.6 Hz,
1H), 7.16 (dd,J: 8.5, 59
Hz, 1H), 6.82 (11,7: 8.4, 4.1
Hz, 2H), 6.59 (1d, .1: 8.2,
2.5 Hz, 1H), 6.53 (dd, .1:
HRMS-ESI (m/z) 10.8, 2.4 Hz, 1H), 5.67 (dq, J
(Thin ?lm)
([M+Na]_) calcd for = 12.3, 6.1 Hz, 1H), 4.97 (d,
3364, 2978,
288 C25H31F2NN305, .1: 6.5 Hz, 1H), 4.73 (d, .1:
1709, 1600,
486.2063, found, 10.2 Hz, 1H), 4.25 —4.04
1496,1161
486.2063 (m, 1H), 3.78 (s, 3H), 2.42
(s, 3H), 1.42 (s, 9H), 1.21 (d,
J: 6.1 Hz, 3H), 0.92 (d,J:
7.2 Hz, 3H).
"’F NMR (376 MHz, CDC13)
—113.52, -116.98.
'H NMR (400 MHz, CDCH)
7.32 — 7.27 (m, 1H), 7.23 —
7.14 (m, 1H), 6.81 —6.71 (m,
2H), 6.61 (td, .1: 8.3, 2.5
Hz, 1H), 6.54 (dd, J = 10.8,
2.5 Hz, 1H), 5.79 (dq,J=
11.8, 6.1 Hz, 1H), 4.95 (d, .1
HRMS-ESI (/17 Z)
(Thin ?lm) : 7.1 Hz, 1H), 4.76 (d, J:
([M+Na]_) calcd for
3364, 2979, 10.1 Hz, 1H), 4.21 —4.05
289 / F3NN305,
Z. 1710, 1601, (m, 1H), 3.76 (s, 3H), 1.42
”i 490.1812; found,
1501, 1162 (s, 9H), 123 (d, J: 63 Hz,
490.1809
3H), 0.90 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
—1 1215 (d, J: 44.2 Hz), -
112,17 (d,./:44.3 Hz), -
112.91.
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.30 (dd, J: 8.4, 6.2 Hz,
1H), 7.03 (dd, J: 8.6, 6.6
Hz, 1H), 6.80 (d, J: 8.7 Hz,
2H), 6.58 (d, J: 9.2 Hz,
2H), 5.65 (dq, .1: 9.9, 61
(Thin ?lm) HRMSEESI (’7’ Z) Hz, 1H), 4.93 (d, J: 6.9 Hz,
5565, 2979,M
([M+Na] ) calcd for
1H), 4.75 (d, J— 9.9 Hz,4 _
290 CNHWFNNaO;
1709, 1497, 486 21063 found, 1H), 4.18 4 4.04 (m, 1H),
1450, 1160 ‘486 21067 ’ 3.84 (s, 3H), 2.28 (s, 3H),
' 1.42 (s, 9H), 1.24 (d, J: 6.2
Hz, 3H), 0.85 (d, .1: 7.2 Hz,
19F NMR (3 76 MHz, CDCH)
6 -11294, -11745.
1H NMR (400 MHz, CDCl;)
7.30 (dd,./: 8.1, 5.8 Hz,
1H), 7.18 — 7.07 (m, 1H),
6.90 — 6.75 (m, 4H), 5.67
(dq,.1: 11.7, 6.5 Hz, 1H),
4.92 (d, J: 6.7 Hz, 1H), 4.61
(Thin ?lm) HRMS'PSI (m/Z) (d, J = 10.1 Hz, 1H), 4.19 —
([M+Na] ) calcd for
5564, 2980,M 5.95 (m,5 1H), 2.29 (s, 5H),5
291 CuHmFxNNaOd
1711, 1499, 47-41H862f0und’ 1.42 (s, 9H), 1.27 (d, J: 6.3
1163 ‘ 1 ’ Hz, 3H), 0.85 (d, J: 7.2 Hz,
474.1863
191: NMR (376 MHz, CDC13)
6 -1 1 1.50 (d, .7: 7.3 Hz), -
112.52(d,J:7.1 Hz), _
116.50.
[Annotation] Mel.Chan
None set by an
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H. 13C. 191:)
1H NMR (400 MHz. CDC13)
for both diastereomers of a
1:1 mixture (1 7,18 - 7.09 (m.
2H). 7.01 — 6.87 (m, 10H).
.76 — 5.58 (m, 2H), 5.03 (d.
J: 5.4 Hz, 1H), 5.01 (d, J:
(Thin ?lm) 4.9 Hz. 1H), 5.01 — 4.90 (m.
3363, 2979, 2H), 4.20 — 4.06 (m, 2H),
292 2939. 2838, 3.92 (d, J: 2.1 Hz. 3H), 3.89
17121586, (d,J=2.0Hz,3H).3.81(d.
1477 J=1.9 Hz,3H).3.80(d,J=
1.9 Hz. 3H). 1.44 (s. 9H).
1.42 (s. 9H), 1.25 (d, J: 6.6
Hz, 3H). 1.23 (d. J = 6.3 Hz.
3H).1_17(d..1: 7.1 Hz,
3H). 0.90 (d, J: 7.2 Hz,
lH NMR (400 MHz, CDClg)
major diastereomer of a 2:1
mixture (1 7.15 (dt, J: 9.6.
3.0 Hz. 1H). 6.93 (td, .1:
. 8.8, 8.2.3.1Hz.1H), 6.89 —
:21:12ng 6.81 (m. 2H), 6.80 — 6.68 (m.
293 5339’ 1712’ 2H). 5.84 (dd. J : 9.6. 6.2
Hz, 1H). 4.98 (s. 1H), 4.86
14957 1455
(d. J: 9.2 Hz, 1H). 4.24 —
4.07 (m, 1H). 3.82 (s, 3H).
3.74 (s. 3H), 1.42 (s, 9H),
1.23 (d. J = 6.3 Hz. 3H), 0.90
(d. .1: 7.2 Hz, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd.
MASS N1VJR
No. (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
6 7.194 7.10 (m, 2H), 7.104
7.07 (m, 4H), 7,03 4 6.98 (m,
1H), 6.98 — 6.92 (m, 1H),
.76 (dq, .1: 10.3, 6.1 Hz,
1H), 4.94 (d, .1: 7.9 Hz,
1H), 4.18 — 4.03 (m, 1H),
3.94 (d, .1: 10.3 Hz, 1H),
2.30 (s, 3H), 2.28 (s, 3H),
1.42 (s, 9H), 1.22 (d, J: 6.1
ESIMS m z 412
Hz, 3H), 0.76 (d, J: 7.2 Hz,
294 ([M+H]+)
13C NMR (101 MHz,
CDC13) missing one
aromatic C signal due to
overlap d 172.84, 141.56,
141.27, 138.32, 137.91,
, 128.87, 128.60,
128.34, 127.62, 127.30,
125.06, 124,89, 7320, 57.91,
53.39, 49.25, 28.31, 21.46,
21.42, 19.32, 18.01.
1H NMR (400 MHz, CDC13)
7.32 — 7,21 (m, 5H), 7.21 —
7.15 (m, 1H), 6.86 (dd,J=
8.0, 1.7 Hz, 1H), 6.79 (dd, .1
:11.3,1.6 Hz, 1H), 5.85 4
ESIMS m z 416 5.72 (m, 1H), 5.04 — 4.94 (m,
295 ([M+H]+) 1H), 4.39 ((1.1: 10.1 Hz,
1H), 4.14 (p, J: 7.4, 6.8 Hz,
1H), 2.26 (s, 3H), 1.42 (s,
9H), 1.24 (d, .1: 6.1 Hz,
3H), 0.90 4 0.81 (m, 3H).
19F NMR (376 MHz, CDC13)
6 -1 18.88.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No, (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8 7.28 4 7,17 (m, 3H), 6.99 4
6.93 (m, 2H), 6.88 (dd, J:
8.0, 1.7 Hz, 1H), 6.80 (dd, J
= 11.2, 16 Hz, 1H), 5.74
(dq, J: 9.9, 6.2 Hz, 1H),
ESIMS m z 434
4.98 (d, J: 7.9 Hz, 1H), 4.37
296 +)
(d, J: 10.0 Hz, 1H), 4.22 4
4.07 (m, 1H), 2.27 (s, 3H),
1.42 (s, 9H), 1.23 (d, J: 6.2
Hz, 3H), 0.88 (d, J: 7.5 Hz,
19F NMR(376 MHz, CDC13)
8 —1]5.62, —118.85.
1H NMR (400 MHz, CDC13)
7.22 (1, .1: 8.0 Hz, 1H),
7.19 4 7.13 (m, 2H), 7.07 (d,
J: 7.9 Hz, 2H), 6.85 (dd,J=
8.0, 1.8 Hz, 1H), 6.77 (dd, J
:112, 1.6 Hz, 1H), 5.83 4
ESIMS m z 430 5.69 (m, 1H), 5.03 (d,J= 8.0
Hz, 1H), 4.35 (d, J: 10.3
297 ([M+H]+)
Hz, 1H), 4.19 4 4.05 (m,
1H), 2.27 (s, 3H), 2.24 (s,
3H), 1.41 (s, 9H), 1.23 (d, J
: 6.1 Hz, 3H), 0.86 (d, J:
8.4 Hz, 3H),
19F NMR (376 MHz, CDC13)
8 4118,95.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No. (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.31 - 7.22 (m, 4H), 7.22 -
7.11 (m, 1H), 7.12 - 7.02 (m,
2H), 6.91 (dd, J: 9.4, 8.2
Hz, 1H), 5.74 (dq, .1: 10.1,
6.2 Hz, 1H), 4.92 (d, .1: 7.9
,. ESIMS m z 416
,,/Z.r.’: Hz, 1H), 4.17 _ 4.04 (m, 1H),
4,5,,
298 ([M+H]+)
,,,1! 3.97 (d,J= 10.2 Hz, 1H),
f 2.23 (d, .1: 1.9 Hz, 3H), 1.41
(s, 9H), 1,23 (d, J: 6.2 Hz,
3H), 0.76 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
-12018.
1H NMR (400 MHz, CDC13)
7.23 (dd, J: 8,6, 6.6 Hz,
1H), 7.07 _ 7.01 (m, 2H),
6.88 (t, J: 9.3 Hz, 1H), 6.60
(td, J: 8,3, 2.6 Hz, 1H),
6.54 (dd, .1: 109,25 Hz,
1H), 5.72 (dq, J: 11.8, 6.0
ESIMS m z 464
Hz, 1H), 4.95 (d, J: 8.0 Hz,
299 ([M+H]+)
1H), 4.44 (d, .1: 10.3 Hz,
1H), 4.19 - 4.07 (m, 1H),
3.78 (s, 3H), 2.22 (d, J: 1.9
Hz, 3H), 1.42 (s, 9H), 1.20
(d, J: 61 Hz, 3H), 0.86 (d,
J: 7.2 Hz, 3H).
”P NMR (376 MHz, CDC13)
—113.49, —120.41.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No, (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
7.24 (dd, .1: 9.6, 5.6 Hz,
1H), 7.16 (t, J: 7.9 Hz, 1H),
6.85 (dt, J: 10.4, 2.4 Hz,
3H), 6,79 (dt, .1: 1 1,3, 1.1
Hz, 1H), 5.70 (dq, .1: 10.2,
ESIMS 777 Z 448 6.2 Hz, 1H), 4.99 (d, J: 8.0
([M+H]+) Hz, 1H), 4.61 (d, J: 10.1
Hz, 1H), 4.22 4 4.09 (m,
1H), 2.39 (s, 3H), 2.26 (s,
3H), 1.42 (s, 9H), 1.25 (d, J
: 6.1 Hz, 3H), 0.92 (d, .1:
7.2 Hz, 3H)
19F NMR (376 MHz,CDC13)
6 —116.47, 0.
1H NMR (400 MHz, CDCl;)
7.30 4 7.21 (m, 2H), 6.92 4
6.85 (m, 1H), 6.85 4 6.74 (m,
3H), 5,84 4 5.73 (m, 1H),
4.97 (d, .1: 7.9 Hz, 1H), 4.68
(d, J: 10.0 Hz, 1H), 4.22 4
ESIMS m z 452
4.07 (m, 1H), 2.28 (s, 3H),
([1V1+H]+) 1.42 (s, 9H), 1.26 (d, .1: 6.2
Hz, 3H), 0.90 (d, J : 73 Hz,
”P NMR (376 MHz, CDC13)
-11163 (d,J= 7.5 Hz), 4
112.07 (61,]: 7.0 Hz), 4
118,16.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No, (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.29 4 7.21 (m, 4H), 7.19 4
7.13 (m, 3H), 7.09 (d, J: 7.9
Hz, 2H), 5.77 (dq, J: 10.3,
6.1 Hz, 1H), 4.92 (d, .1 : 7.9
Hz, 1H), 4.17 4 4.04 (m,
(Thin ?lm) 1H), 3.99 (d, J: 10.3 Hz,
3366, 2979. Wilfg?ff”) 1H), 2.28 (s, 3H), 1.41 (s,
2932, 1713, 9H), 1.23 (d, .1: 6.1 Hz,
1496, 1452, calcd for 3H), 0.75 (d, J = 7.2 Hz,
1365, 1306, C24H32NO4, 3H).
1248, 1211, 398.2326; found,
1165, 1053, 398.2328 13C NMR (126 MHz,
699 CDC13) 5 172.83, 154.94,
141.81, 138.26, 136.50,
, 129.46, 128.47,
127.93 (d, J: 3.6 Hz),
, 120.94, 79.63,
73.17, 57.62, 49.18, 34.67,
28.31, 20.97, 19.30, 18.00.
'H NMR (400 MHz, CDC13)
7.26 (d, J: 4.5 Hz, 5H),
7. 18 (d, J = 7.9 Hz, 2H), 7.05
(d, .1: 7.9 Hz, 2H), 5.77 (dq,
J: 10.0, 6.2 Hz, 1H), 4.94
(d, J: 7.9 Hz, 1H), 4.18 —
4.05 (m, 1H), 3.99 (d, J:
HRMS-ESI (/17 Z)
(Thin ?lm) 10.0 Hz, 1H), 2.26 (s, 3H),
([M+H]+)
3371, 2978, 1.42 (s, 9H), 1.22 (d, J = 6.2
2931, 1712, calcd for Hz, 3H), 0.80 (d, .1: 7.2 Hz,
w 0 Lu ~11",<[4.11n. 1495, 1451, C24H32NO4, 3H).
1365, 1165, 398.2326, found,
1051, 699 3982324 13CN1\4R(126 MHz,
CDC13)6172.83, ,
141.52, 138.41, 136.15,
129.12, 128.73, 128.21,
128.05, 127.95, 126.79,
124.35, 79.63, 73.17,
57.47, 49.21, 34.67, 28.31,
.94, 19.30, 18.08.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
CmNE,d. MP IR NMR
(0C) (cm'l) (H 13C, 191:)
1H NMR (400 MHz, CDC13)
7.25 i 7.20 (m, 2H), 7.15
(d, J: 8.1 Hz, 2H), ,
J: 7.9 Hz, 2H), 6.96 (1, J:
8.7 Hz, 2H), 5.72 (dq, J:
9.7, ()2 Hz, 1H), 4.93 (d, .1:
7.9 Hz, 1H), 4.17 — 4.06 (m,
1H), 3.99 (d, J: 9.8 Hz,
(Thin?lnv 335212271‘51?’6‘é‘i‘23‘
3371, 2979, HRMS-IESI (m/Z) 3H)” 0'81 (d1 J: 7‘2 HZ’
2932, 1712, ([M+Na] )calcd for ’ ' 51% ‘ ’
" )‘
304 1508, 1452, C24H30FNO4Na,
1366 1222 4382051 f n ;
1160710537 50211 d? LCNMRW6 MHZ’
8116 1 CDC13)5172.80, 16165 (d,
J: 2455 Hz), 154.94,
138.13, 137.32 (d,J=3.2
Hz), 136,35, 12952 (d, J:
7.9 Hz), 129.22, 127.89,
126.12 (d,J= 7.8 Hz),
115.56 (d,J= 21.3 Hz),
7968, 73.01, 56.60, 49.19,
34.67, 31.59, 28.31, 20.95,
19.22, 18.07.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
ed set by Mel.Chan
Cmpd. \‘ MP IR NMR
No. (0C) (cm'l) (1H. 13C. 191:)
1H NMR (400 MHz. CDC13)
8 7.31 4 7.23 (m. 7H). 6.98 4
6.92 (m. 2H). 5.75 (dq, J:
.0. 6.2 Hz. 1H). 4.91 (d. J
= 7.8 Hz. 1H). 4.18
— 4.07
(m. 1H). 4.02 (d. J: 10.0
(Thin ?lm) Hz. 1H). 1.42 (s. 9H). 1.23
3371. 2979. (d. J: 6.2 Hz. 3H). 0.83 (d.
\ 2933. 1710. ESI?€§4:’HZF)02~2 .1: 7.2 Hz. 3H).
305 1509. 1452.
:‘> 1366. 1222. 13C NMR (126 MHz.
1160.105]. CDC13)5 172.80. 161.61 (01.
699 .1: 2452 Hz). 154.93.
141.02. 137.26 (d.J=3.4
Hz). 129.55 (d. .1: 7.9 Hz).
128.86. 127.99. 127.05.
115.29 (d.J=21.2Hz).
79.74. 73.05. 57.10. 49.18.
34.67. 28.31. 19.29. 18.12.
La) [0 La)
[Annotation] an
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.26 4 7.21 (m, 2H), 7.14
(d, J: 8.2 Hz, 2H), 7.09 (d,
J: 8.1 Hz, 2H), 6.98 — 6.90
(m, 2H), 5.73 (dq, J: 10.2,
6.1 Hz, 1H), 4.91 (d, .1: 8.0
Hz, 1H), 4.17 — 4.06 (m,
1H), 3.98 (d, J: 10.2 Hz,
(Thin ?lm) 1H), 2.29 (s, 3H), 1.42 (s,
3371, 2979, 9H), 1.22 (d, J: 6.1 Hz,
2932, 1712, 3H), 0.82 Ed, J: 7.2 Hz,
ESIMS m Z 4382
306, 1509, 1452, ([M+Na]+) 3H).
1366,1222,
1161,1052, 13CN1\4R(1261V1Hz,
815 CDC13)6172.80, 161.56 (d,
J : 245.0 Hz), 154.93,
138.04, 137.58(d,J=3.3
Hz), 136.69, 129.54, 129.43
((1, J: 7.8 Hz), 127.82,
115.25 (d,J=21.2 Hz),
79.72, 73.11, 56.76, 49.18,
34.67, 28.31, 20.97, 19.28,
18.12.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Chnpd. 0g, REP DR P?y?k
No. (0C) (cm'l) (1H. 13C. 191:)
1H NMR (400 MHz, CDC13)
8 7.33 4 7.24 (m, 5H), 7.22 4
7.14 (m, 111), 6,86 4 6.73 (m,
2H), 5.84 4 5.72 (m, 1H),
4.90 (d, J: 8.0 Hz, 1H), 4.40
(d, .1: 10.2 Hz, 1H), 4.18 4
4.05 (m, 1H), 1.42 (s, 9H),
(Thin ?lm) HRMS-ESI (m z) 1.26 (d, J: 6.1 Hz, 3H), 0.78
3370, 2980, ([M+H]+) (d, J: 7.2 Hz, 311).
§ 712’
cdcdibr 1~
307 1503, 1453, ”C NMR (126 MHz,
C3~H7 ENC
:: 1366, 1 I64, 42019811611146 CDC13) 5 172.74, 162.98 4
1053, 966, 161.09 (m), 160.06 (dd, J4
420.1995
851,698 169.5, 12.1 Hz), 154.93,
140.15, 129.79, 128.61,
128.22, 127.00, 124.39 (d,J
=18.6Hz),111.62(d,J=
19.5 Hz), 104.70 4103.41
(m), 79.71, 72.30, 49.40,
49.15, 34.67, 28.31, 18.97,
17.99.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
CmNE.d. MP 1R NMR
(0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
6 7.25 4 7.20 (m, 1H), 7.18
(d, J: 8.1 Hz, 2H), 7.07 (d,
J: 7.6 Hz, 2H), 6.85 — 6.72
(m, 2H), 5.76 (dtd, .1: 9.5,
6.8, 5.5 Hz, 1H), 4.92 (d, .1:
7.8 Hz, 1H), 4.36 (d, J: 10.0
Hz, 1H), 4.19 — 4.01 (m,
. - lH,2.27
(Thm ?lm) 911)), 1.25((d, J=) 6.2 H(z,s,3H,1.42 s,
3364, 2980, HRMS-IESI (m/Z) 3H) 0 82 (d J: 7 2 HZ
2933, 1713, ([M+Na] )calcd for ’ ' ”Ii ‘ ’
" )‘
308 1502, 1453, C24H26F2NO4Na,
11306563, 1916664, 96519ggund, 13C NMR (126 MHZ,
850 ° ‘ CDC13)6172.74, 161.98
(dd,J: 167.8, 11.9 Hz),
160.01 (dd,J=167.8, 11.9
Hz), 154.93, 137.05,
136.57, 129.90, 129.24,
, 124.66 (d,J=11.5
Hz), 11157 (d, J = 20.4 Hz),
104.69 4 102.95 (m), 79.70,
72.38, 49.18, 48.94, 28.31,
.97, 18.97, 18.07.
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. 5333;, MP IR NMR
No, (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
7.29 4 7.19 (m, 3H), 6.99 4
6.93 (m, 2H), 6.86 4 6.75 (m,
2H), 5.81 — 5.70 (m, 1H),
4.90 (d, J: 7.9 Hz, 1H), 4.37
(d,.]: 10.1 Hz, 1H),4.214
. 4.06 (m, 1H), 1.42 (s, 9H),
gang? 1.26 (d, J = 6.2 Hz, 3H), 0.85
‘ ‘ 1 ’ HRMS—ESI (m z) (dd, .1: 7.8, 1.1 Hz, 3H).
1711, 1604, -
([M+Na] )calcd for
;\ 1502 1454 1‘
309 C23H26F3NO4Na, ”C NMR (126 MHz,
1,) 8 07 1366’
:3 {224‘ 1161’ 460.1706; found, CDC13) 5 172.71, ,
10531 966’ 460.1712 162.71, 161.37, 161.28,
8511 ’ 160.87, 160.75, 159.39,
1 159.30, , 135.92,
12976 (d, J: 7.7 Hz),
115.44 (d, J: 21.3 Hz),
11171 (d, .1: 180 Hz),
104,71 4 103.96 (m), 79.80,
72.20, 49.16, 48.78, 34.67,
28.30, 18.99, 18.09.
HRMS-ESI(/1Iz)
([M+H]+)
calcd for
C26H38N02,
396.2897, found,
396.2896
1H NMR (400 MHz,
Acetone—d6) 5 7,3] 7 7.21
(m, 4H), 7.15 (ddd,.l: 10,9,
HREEEEJ” Z) 8.5, 2.5 Hz, 4H), 5.87 (dq, J
= 10.0, 6.0 Hz, 1H), 4.05 (d,
calcd for .1: 10.5 Hz, 1H), 3.85 (q, .1:
:: C24H34N02, 7.2 HZ, 1H), 3.31 (dt, J:
368.2584, found, 33, 1.7 Hz, 3H), 2.91 — 2.73
3682584 (m, 2H), 1.26 (d, .1: 6.1 Hz,
3H), 1.19 (1,]: 6.7 Hz,
12H), 0.81 (dd, J: 7.3, 2.8
Hz, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd. MP 1R NMR
No. (CC) (cm'l) (1H, 13C, 191:)
HRMS-ESI (m/z)
([M+H]+)
calcd for
340.2271; found,
340.2273
1H NMR (400 MHz,
Acetone—d6) 5 7.34 (dd, ./ :
8.7, 5.7 Hz, 1H), 7.26 (dd, J
= 8.7, 5.8 Hz, 1H), 7.02
HRMS-ESI(/11z) 6.80 (m, 5H), 5.75 (dq, J:
([M+H+] ) 98,6.1Hz, lH,4.59 d,J:
9.8 Hz, 1H), 3.96 (q, J: 7.2
called for
313 Hz, 1H), 3.72 7 3,60 (m,
C211H24F2N02,
2H), 2.40 (s, 3H), 2.37 (s,3 3
,48 1770. f3 nd
‘348 1778?)” 7 3H), 1.34 (d, J: 6.2 Hz,
' 3H), 1.03 (d, .1: 7.3 Hz,
191: NMR (376 MHz,
Acetone) 6 —l [9,66, —l20.05.
ESIMS m z 320
3 14 ([M+H]+)
ESIMS 777 Z 320
315 ([M+H]+)
ESIMS m 2 380.5
316 ([M+H]+)
ESIMS 777 Z 374.4
317 ([M+H]+)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No, (0C) (cm'l) (1H, 13C, 191:)
1:“. ESIMS m z 298
\ +
318 ([M+H], )
ESIMS m z 334
319 £315 ([M+H] )
ESIMS m Z 420
320 ([M+H]+)
ESIMS
:33‘ 777 Z 428
321 ([M+H1+)
58511“ 117210)Th' f1
HRMS—ESI(I11Z)
7 7 +
([Mm] )
1494, 1451,
1253, 1231, calcd for
1204, 1 1 17, ClegzNog,
1080, 1046, 45, found,
871, 746, 44
ESIMS 777 Z 4123
.tx‘ +
ESIMS m 2 408.4
324 ([M+H]+)
ESIMS m 2 440.3
325 ([M+H]+)
ESIMS m 2 400.4
326 ([M+H]+)
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No (CC) (cm'l) (H, 13C, 191:)
ESIMS m z 404
327 ([M+H]+)
ESIMS m z 372
328 ([M+H]+)
ESIMS m z 372
329 ([M+H]+)
ESIMS m z 380
330 ([M+H]+)
ESIMS m z 380
33 1 ([M+H]+)
‘H NMR (500 MHz,
Methanol-d4) 8 6.74 (dddd, J
= 17.6, 8.0, 3.7, 1.8 Hz, 4H),
6.58 (ddt, .1: 12.2, 10.0, 2.3
Hz, 2H), 5.83 (dq, J : 10.2,
Wiggl?m/Z) 6.1 Hz, 1H), 4.13 (d, J = 10.3
([ 1 )
Hz, 1H), 3.93 (q, .1: 7.2 Hz,
calcd for 1H), 3.78 (s, 3H), 3.77 (s,
C20H24F2NO4, 3H), 1.28 (d, J: 6.2 Hz,
380.1668, found, 3H), 1.00 (d, J: 7.3 Hz, 3H)
380. 1649 (NH protons not observed).
191: NMR (471 MHz,
Methanol—d4) 5 -1 12.85 (t, J
= 10.0 Hz), —113.22 (t,J=
.3 Hz).
v) La) 0
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
. \ MP IR NMR
(0C) (cm'l) (H 13C, 191:)
1H NMR (500 MHz,
Methanol—d4) 6 6.51 (dd, J:
HRMS—ESI (m z) 5.2, 2.3 Hz, 4H), 6.35 (dt, J
([M+H]+) = 13.0, 2.2 Hz, 2H), 5.82
(dq,J= 10.4, 6.1 Hz, 1H),
333 3.99 (d, J: 10.4 Hz, 1H),
C C??fg
«1 3.89 (q,J= 7.2 Hz, 1H), 3.75
404 222063;? £63m
‘404 21038 ’ (s, 6H), 3.74 (s, 6H), 1.27 (d,
' ./:6.2 Hz, 3H), 0.96 (d, .1:
7.3 Hz, 3H) (NH protons not
observed).
1H NMR (500 MHz,
Methanol-d4) 5 6.75 (d, J =
4.0 Hz, 2H), 6.69 (dt, J:
HRMS-ESI(/1Iz) 6.6, 1.9 Hz, 2H), 6.61 (s,
([M+H]+) 1H), 6.58 (d, J: 2.3 Hz,
1H), 5,82 (dq, .1: 10.4, 6.1
334 \ Hz, 1H), 3.97 (d, J: 10.5
C C??fg
:5 Hz, 1H), 3.85 (q, J = 7.3 Hz,
372 2221633, £0311d
‘372 21146 ’ 1H), 3,75 (s, 3H), 3.74 (s,
‘ ' 3H), 2.29 (s, 3H), 2.27 (s,
3H), 1.25 (d, J: 6.2 Hz,
3H), 0.92 (d, J = 7.2 Hz, 3H)
(NH protons not observed).
1H NMR (500 MHz,
Methanol—d4) 6 6.75 (d, J:
4.0 Hz, 2H), 6.69 (dt, J:
HRMS-ESI (m/Z) 6.6, 1.9 Hz, 2H), 6.61 (s,
([M+H]+) 1H), 6.58 (d, .1: 2.3 Hz,
. 1H), 5.82 (dq, .1: 104,61
335 \ Hz, 1H), 3.97 (d, J: 10.5
C C3???
::~: Hz, 1H), 3.85 (q, J: 7.3 Hz,
372 222163 fodnd
’ 1H), 3.75 (s, 3H), 3.74 (s,
3,72 2146 ' 3H), 2.29 (s, 3H), 2.27 (s,
3H), 1.25 (d, J: 62 Hz,
3H), 0.92 (d, .1: 7.2 Hz, 3H)
(NH protons not observed).
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS NMR
No. (‘0 (cm ) (1H7 13c:1 19F)
1HNMR(500 MHz,
Methanol-d4) 5 7.03 (dd, .1:
11,9, 7.5 Hz, 2H), 6.92 2
6.80 (m, 4H), 5.88 (dq, .1:
ESIMS m 2 372.1
.5, 6.1 Hz, 1H), 4.05 (d, .1
VJ La) 0‘ ([M+H]+) :104 Hz, 1H), 3.88 (q, .1:
7.2 Hz, 1H), 3.80 (d, J: 1.0
Hz, 6H), 2.12 (s, 3H), 2.11
(s, 3H), 1.26 (d, .1 : 6.1 Hz,
3H), 0.90 (d, .1: 7.2 Hz, 3H)
(NH protons not observed).
1H NMR (500 MHz,
ol-d4) 5 7.15 — 7.06
(m, 4H), 7.03 (q, .1: 8.5 Hz,
2H), 5.77 (dq, .1: 10.1, 6.2
HRMS-ESI (m/z) Hz, 1H), 4.06 (d, J: 10.0
([1v1+H]+) Hz, 1H), 3.93 (q, .1 : 7.3 Hz,
»\»\ 1H), 3.83 (s, 3H), 3.82 (s,
calcd for
Lu Lu \1 3H), 1.25 (d, J: 6.1 Hz,
C20H24F2NO4,
3H), 1.00 (d, .1: 7.3 Hz, 3H)
68; found,
(NH protons not observed).
380.1667
191: NMR (471 MHz,
Methanol—d4) 5 8 (dd,
1: 12.6, 8.5 Hz), —136.53
(dd, .1: 12.6, 8.9 Hz).
1H NMR (500 MHz,
Methanol-d4) 5 7.14 — 7.03
(m, 4H), 6.80 (dd, .1 : 12.7,
8.4 Hz, 2H), 5.77 (dq, .1 :
ESIMS m 2 372.1 10.3, 6.2 Hz, 1H), 3.92 (d, .1
=10.4 Hz, 1H), 3.86 (q, .1:
b) b) 00 ([M+H1+)
7.2 Hz, 1H), 3.78 (s, 3H),
3.76 (s, 3H), 2.15 (s, 3H),
2.14 (s, 3H), 1.23 (d,J= 6.1
Hz, 3H), 0.92 (d, J: 7.3 Hz,
3H) (NH protons not
observed).
v) La) [\J
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz,
Methanol—d4) 8 7,03 (d, J:
3.0 Hz, 1H), 6.90 4 6.80 (m,
HRMS-ESI (m/Z) 3H), 6.75 (ddd, J = 8.9, 4.5,
([M+H]+) 3.1 Hz, 2H), 5.99 (dq, J =
.2, 6.2 Hz, 1H), 4.91 (d, J
calcd for
339 = 10.2 Hz, 1H), 3.89 (q,J=
C H“ N0
3 22 0 6’ 7.2 Hz, 1H), 3.81 (s, 3H),
404.2068, found,
3.73, , (5, 3H), 3.73, , , (S, 3H),,
404 2059'
3.70 (s, 3H), 1.24 (d, J = 6.2
Hz, 3H), 0.97 (d, J = 7.2 Hz,
3H) (NH s not
observed).
23310171211112) HRMS—ESI (m z)
’ ’ (1M+H1+)
1617,1501,
\ 1473, 1429, calcd for
, 1293, 1233, C20H22F1N01,
1189, 1119, 416.1479, found,
1050, 950, 4161479
(Thin ?lm) HRMS-ESI (m’z)
2866, 1742, ([M+H]+)
1500, 1454,
ca C1 d for
341 \ 1378, 1226,
CBHWNOL
1113, 1048,
340.2271, found,,
808 7,92
1, ’ 69
5863,Thin ?lm1748), HRMS-ESI+(m z)
([M+H] )
1736, 1526,
1500, 1456, calcd for
1376, 1238, C22H30N02,
1187, 1116, 340.2271, found,
1048, 810, 340.2274
791, 751
La) La) La)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. \ MP 1R NMR
No, (0C) (cm'l) (1H,1"C, 191:)
(Th'1“ 1m)f1
HRMS-ESI(m'z)
2878, 1751, ,
([Mm1 )
2,, 1738, 1587,
\ 1526, 1494, calcd for
1459, 1240, C20H24F2N02,
1226, 1188, 348.1770; found,
1130,1048, 348.1771
811, 754
(Thin ?lm) SI (m z)
2962, 1747, ([M+H]+)
1596, 1497,
calcd for
344’3 \‘ 1234, 1205,'3
C20H24F2NO4,
1114, 1052,
380.1668; found,,
1034, 829,5
",8016“
811,713 ' ‘
£832)“ 117:2Th' f1
FIRMS—13810112)
7 7 +
([Mm] )
1622, 1583,
1506, 1444, calcd for
3,45 931; 1287, 1254, CZUHNFZNOn
1193, 1116, 380.1668; found,
1050, 1030, 1
872,833
£94311 117212)Th' f1
HRVIS-ESI (m z)
1 7 +
([NHH] )
1615, 1588,
1457, 1417, calcd for
1326, 1241, C22H24F6NO4,
1171, 1116, 480.1604; found,
1032, 873, 480.1607
859,740
ESIMS m 2 408.2
347 ([M+H1+)
La) La) 4;
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. n .
:\§» \9\\ ‘\‘\3 MP
No5 \'\'\x \
§‘_.\\ (‘0 (1H, 13C1 19F)
ESIMS m z 4362
([M+H]+)
ESIMS m z 404.]
([M+H]+)
ESIMS/172 372.1
([M+H]+)
ESIMS m 2 372.1
3 5 1 ([M+H]+)
ESIMS m z 3 80
3: +
352 ([M+H])
ESIMS m z 3 72
i: ([M+H]+)
ESIMS m z 332
([M+H +)
:3 ESIMS m z 316
1‘ +
355 ([M+H] )
ESIMS m z 332
355 ‘5 (Wm?)
ESIMS m z 316
([M+H]+)
La) La) L11
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by an
Cmpd. n .
:\§» \\\\\ ‘\‘\3 MP
No3 \'\'\x \
§‘_-‘\ (‘0 (1H, 13C, 191:)
ESIMS m z 346
358 ii ([M+H]+)
ESIMS m z 330
359 (mm +)
ESIMS m z 346
360 ([M+H]+)
ESIMS m z 350
([M+H]+)
ESIMS m z 334
([M+H]+)
ESIMS m z 350
363 ([M+H]+)
ESIMS m z 334
364 ([M+H +)
ESIMS mw’z
3 6 S 312([M+H]+)
ESIMS m 2 364.2
([M+H]+)
ESIMS/172 368.2
([M+H]+)
La) La) 0
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. n .
:\k \v\\ ‘\‘\A MP
No‘ (0C) (cm 1) (H 13C, 191:)
ESIMS m 2 364.2
368 ([M+H]+)
ESIMS m z 3522
369 ([M+H]+)
ESIMS m z
?W?22;;61// 3 16([M+H]+)
ESIMS m z
334([M+H]+)
ESIMS m z 330
([M+H]+)
ESTMS m z
348([M+H]+)
ESIMS m z 352
22926283 ([M+H]+)
ESIMS m z 316
([M+H]+)
ESIMS m z 364
w,/’/.‘/
T.’ ([M+H]+)
mg,”’ ,1 Lin
La) La) \]
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No, (0C) (cm'l) (1H,13C, 191:)
(Thin ?lm) HRMS-ESI (m/Z)
3408, 2920, ([M+H]+)
1740, 1512,
cam for,
377 1495, 1452,
i C19H24N02,
1232, 1198,'5
298.1802,_ found,
1114, 1048,
2981798
734,699 '
$7117“ {171219) HRMS—ESI (m z)
’ " ([M+H]+)
.11, 1599, 1515,
1493, 1452, calcd for
*378 1 1228, 1193, C19H21N02,
1139, 1119, 02; found,
1055, 744, 298.1795
(Thin ?lm) HRMS-ESI (m z)
2879, 1747, +)
1602, 1508,
ca C1 d for
379 1454, 1227,
1197, 1116, CWHBFNOZ’
316.1707; found,,
1053 814
;, ’ 316.1703
(Thin ?lm) P11113513??? Z)
2896, 1741,
1604, 1509, calcd for
1453, 1226, C18H21FN02,
1117, 1047, 302.1551, found,
732, 699 302.1548
(Thin ?lm) W151i??? Z)
1603, 1509, calcd for
*381 s; 1459, 1229, C19H23FNOZ,
1117, 1049, 316.1707; found,
813 316.1705
La) La) 00
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No, (0C) (cm'l) (1H, 13C, 191:)
ET?“ ?ll?) HRMS-ESI (m 2)
33 6, 2936,
([N1+H]+)
1743, 1619,
1602, 1503, calcd for
1454, 1235, CmHzoFgNOz,
1208, 1 145, 320.1457, found,
1116, 966, 320.1451
850,699
(Thin ?lm) HRMS-ESI (m z)
3440, 2924, ([M+H]+)
1743’ 1603’
calcd for
383 1502, 1234,
C19H22F2N02,
1208, 1116, ,, ,
334.1613; found,
1100, 1083,
334.1606,,
9667 849
(Thin ?lm) W151i???”
3384, 2935,
384 : 1743, 1603, calcd for
;j\-; 1503, 1228, F3N02,
1 1 17, 966, 338.1362, found,
850 56
(Thin ?lm) HRIEEEES" Z)
3384, 2935,
1743, 1603, calcd for
if: 1503, 1228, C18H10F3N02,
1117, 966, 338.1362, found,
850 338.1356
La) La) 0
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS NMR
No, (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
51205017: 0.6 Hz, 1H),
8.31 (61, J: 8.0 Hz, 1H), 7.97
(d,J= 5.2 Hz, 1H), 7.22
(dddd, J: 11.7, 85, 5.3, 2.6
Hz, 4H), 7.02 4 6.89 (m,
4H), 6.86 (d, J: 5.2 Hz,
1H), 5.72 (dq, J = 9.7, 6.2
Hz, 1H), 4.60 4 4.46 (m,
HRMS-ESI(/1Iz)
1H), 4.05 (d, J: 9.8 Hz,
([M+H]+)
1H), 3.94 (s, 3H), 1.24 (d, J
calcd for : 6.2 Hz, 3H), 1.06 (d, .7:
C25H25FZN2057 7.2 Hz, 3H)
28; found,
471.1726. 13CNMR(101 MHz,
CDC13)6171,56, 168.60,
162.98, 162.87, 160.54,
160.42, 155.41, 148.75,
140.43, 136.83, 136.80,
136.73, 136.70, ,
129.54, 129.46, 115.83,
115.62, 115.50, 115.29,
109.46, 7332,5614, 56.08,
4787,3092, 19.12, 17.67.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No, (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
12.08 (01, J: 0.7 Hz, 1H),
8.20 (d, J: 8.0 Hz, 1H), 7.99
(d, J: 5.2 Hz, 1H), 7.24 —
7.13 (m, 4H), 7.03 — 6.93 (m,
2H), 6.93 4 6.84 (m, 3H),
.69 (dq, J: 9.1, 6.2 Hz,
1H), 4.59 — 4.45 (m, 1H),
4.05 (d, .1: 9.0 Hz, 1H), 3.96
111113151??? Z) (s, 3H), 1,34 (d, J = 72 Hz,
3H), 1.22 (d, J: 6.2 Hz,
calcd for
, 3H).
Czs?stZNZOS,
471.1723, found, 13C NMR (101 MHz,
471.1726. CDC13)6171.26, 168.55,
162.94, 16284, 160.49,
160.40, 155.44, 148.78,
140.44, 136.82, 136.79,
136.46, 136.43, ,
129.74, 129.67, 129.65,
129.57,115.76,115.55,
115.46, 115.24, 109.50,
99.99, 73.34, 56.11, 55.66,
47.80, 18.95, 17.74.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz, CDC13)
812.05(s, 1H), 8.32 (d, J:
8.0 Hz, 1H), 7.98 (d, J: 5.2
Hz, 1H), 7.24 (dd, J: 8.7,
.8 Hz, 1H), 7.14 (dd, J:
8.6, 5.8 Hz, 1H), 6.92 4 6.72
(Thin ?lm) HRIESIEES’” Z) (m, 5H), 5.64 (dq, J: 9.8,
3371,2981, 6.2 Hz, 1H),4.53 (p,J= 7.3
1735, 1649, calcd for Hz, 1H), 4.44 (d, J : 9.7 Hz,
5388 1495, 1261, C27H29F2N205, 1H), 3.94 (S, 3H), 2.38 (S,
954, 800, 499.2039, found, 3H), 2.31 (s, 3H), 1.31 (d, J
728 499.2044 : 6.1 Hz, 3H), 1.10 (d, J:
7.2 Hz, 3H).
19F NMR (471 MHz, CDC13)
8 —1 16.46 (td, J: 88,57
Hz), -116.87 (td,J= 9.0, 5.9
1H NMR (500 MHz, CDC13)
512.12(s,1H),8,38(d,J=
7.9 Hz, 1H), 7.98 (d, J: 5.2
Hz, 1H), 7.29 (d, J = 8.3 Hz,
2H), 7.25 (s, 6H), 6.86 (d, J
: 5.2 Hz, 1H), 5.80 (dq, J:
.3, 6.2 Hz, 1H), 4.48 (p, J
= 7.3 Hz, 1H), 3.98 (d, J:
(Thin ?lm) WISE???" Z) 10.3 Hz, 1H), 3.93 (s, 3H),
3370, 2962, 1.28 4 1.25 (m, 12H), 1.24
1735, 1649, calcd for (s, 9H), 0.83 (d, J: 7.2 Hz,
1527, 1264, C33H43N205, 3H).
1145, 801, 547.3166, found,
729 547.3163 13C NMR (126 MHz,
CDC13)5171.76, 168.50,
155.32, 149.63, 149.44,
, 140.42, 138.71,
,130.51,127.66,
127.63, 125.64, 125.36,
109.37, 74.03, 57.25, 56.05,
4778,3437, 34.32, 31.31,
31.30, 19.33, 17.40.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No, (9C) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz, CDC13)
8 12.12 (s, 1H), 798 (d, J:
.2 Hz, 1H), 7.23 (dd, J :
8.3, 2.6 Hz, 5H), 7.13 (d,J=
7.9 Hz, 2H), 7.09 (d, .1: 79
Hz, 2H), 6.86 (d, .1 : 5.2 Hz,
1H), 5.80 (dq, J: 10.4, 6.1
Hz, 1H), 4.49 (p, J: 7.3 Hz,
1H), 3.98 (d, .1: 10.2 Hz,
(Thin ?lm) HRMS-ESI (m/z) 1H), 3.93 (s, 3H), 2.82 (tp, J
3370, 2959, ([M+H]+) = 13.9, 6.9 Hz, 2H), 1.25 (d,
1734, 1649, .1: 6.1 Hz, 3H), 1.20 (d, J:
calcd for
390 “r 1527, 1450, 69 Hz, 6H), 1.16 (d, J: 6.9
C H“ N 0 “ 31 9 9
1280, 1145, 5’ Hz, 6H), 0.86 (d, J = 7.2 Hz,
519.2853, found,
1045, 801, 3H).5
729 ‘519 2848'
13C NMR (126 MHz,
CDC13)6171.75, 168.50,
155.32, 148.70, 147.36,
147.20, 140.41, 139.09,
138.58,130.51,127.91,
, 126.50, 109.37,
7397,5739, 56.05, 47.80,
3364,3362, 23.98, 23.97,
23.93, 19.31, 17.45.
La) 4; La)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No, (0C) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz, CDC13)
8 12.12 (s, 1H), 8,36 (d, J:
7.9 Hz, 1H), 7.98 (d, J: 5.2
Hz, 1H), 7.07 4 6.89 (m,
6H), 6.86 (d, ,1: 5.3 Hz,
1H), 5.76 (dq, .1: 10.3, (11
Hz, 1H), 4.52 (p, J: 7.3 Hz,
1H), 3.94 (s, 3H), 3.91 (d, J
(Thin ?lm) HRMS—ESI (m z) : 10.3 Hz, 1H), 2.17 (dd, .1:
3370, 2959, ([M+H]+) 20.2, 12.3 Hz, 12H), 1.24 (d,
1734, 1649, J: 6.1 Hz, 3H), 0.99 (d, J:
62116d for
391 1576, 1450, 7.2 Hz, 3H).
CZQHBSNZOE
1262’ ”47’
491 2540 found
1050, 800, '491 21540 3 6"C NMR(126 MHz,
728 ‘ CDC13)6 171.72, 168.48,
, 148.69, 140.38,
139.15, 138.98, 136.84,
,135.01,134.59,
130.50, 12993, 129.62,
129.33, 129.28, 125.27,
124.99, 109,35, 73.76, 57.12,
56.05, 47.88, 19.88, 19.79,
19.30, 924, 17.67.
1H NMR (400 MHz, CDC13)
HRMS-ESI(I1zz) 5 11.51—1126(m, 1H),
(Thin ?lm) ([M+H]+) 8.72 4 8.46 (m, 1H), 8.10 4
3358, 2936, 7.95 (m, 1H), 7.24 4 7.13 (m,
621166 for
392 1749, 1659, 4H), 7.03 4 6.82 (m, 5H),
C25H77F
::~: 1508, 1223, 525 1413: ?guna 5.88 4 5.70 (m, 1H),5.314
1131 @5114“ 3 5.11 (m, 1244.04(m,
1H),4.014 3,93 (m, 3H),
1.32 —1.25(m,3H).
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (300 MHz, CDC13)
12.11 (d, 7:07 Hz, 1H),
8.34 (d, J: 8.0 Hz, 1H), 7.97
, (d, J: 5.3 Hz, 1H), 7.35 (dd,
(Thin ?lm) #515535?” J: 8.5, 67 Hz, 1H), 7.25 —
3371, 2939, 7.08 (m, 1H), 6.86 (d, .1: 5.2
1734, 1649, calcd for Hz, 1H), 6.61 — 6.45 (m,
1599, 1500, F2N207, 4H), 5.89 (dq, J: 9.6, 6.1
1277, 1 150, 53 1 . 193 7, found, Hz, 1H), 4.83 (d, .1 : 9.7 Hz,
1034, 953 531.1926 1H), 4.71 — 4.44 (m, 1H),
3.94 (s, 3H), 3.83 (s, 3H),
3.73 (s, 3H), 1.23 (d, J: 6.2
Hz, 3H), 1.09 (d, J : 7.2 Hz,
1H NMR (400 MHz, CDC13)
512.09(s, 1H), 8.41 (d,J=
7.9 Hz, 1H), 7.98 (d, .1: 5.2
Hz, 1H), 7.32 _ 7.12 (m,
10H), 6.86 (d, J: 5.2 Hz,
HRMS—ESI (m z) 111? if; (q’ i: :3 El *
([M+H]+) )7“ -» (p7,; ~ Z»
1H), 3.94 (s, 3H), 1.75 (s,
calcd for 3H), 1.20 — 1.14 (m, 6H).
C26H29N2057
448.2071; found, 13C NMR (101 MHz,
449.2081. CDC13)6171.61, 168.58,
155.36, 148.74, 146.44,
144.98, 140.40, ,
128.16, 128.10, 127.93,
127.35, 126.33, 126.16,
109.43, 7621,5606, 5040,
48.00, 23.98, 17.94, 15.94.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No, (CC) (cm'l) (H 13C, 191:)
1:1 mixture of reomers.
1H NMR (500 MHz, CDC13)
612.14(s, 1H), 12.09 (s,
1H), 8.34 (d, J: 8.0 Hz,
. 1H), 8.24 (d, J: 79 Hz,
$32)“ $91211) 1H), 8.00 (d, .1 : 5.2 Hz,
1734’ 1648’ HRMS-ESI (m/z) 1H), 7.98 (d, J = 5.2 Hz,
’ ’ ([M+H]+) 1H), 7.32 — 7.17 (m, 9H),
1575, 1527,
, 7.1677.10(m,1H),6.88(d,
, 1494, 1480, calcd for
395 J—5.2 Hz, 1H),6.86(d,J—_ _
1450, 1279, C25H3-N205,
.2 Hz, 1H), 5.88—5.75 (m,
1262, 1242, 435.1914, found,, ,
1H)” 45644401" 1H)”
1144 1047 435 19243
909* 729 ’ ' 4,07 (d, J: 5.6 Hz, 1H), 4.05
7’02 ’ (d, J: 6.1 Hz, 1H), 3.95 (s,
3H), 3.94 (s, 1H), 1.29 (d, .1
: 7.2 Hz, 3H), 1.26 (d, J:
6.2 Hz, 3H), 1.24 (d, J = 6.2
Hz, 3H), 0.97 (d, .1: 7.2 Hz,
311).
1H NMR (400 MHz, CDC13)
11.96 (s, 1H), 8.24 (d, .1:
7.9 Hz, 1H), 7.98 (t, J: 54
(Thin ?lm) HRMSEEPSIIEm/Z) Hz, 1H), 7.63 — 7.59 (m,
([ ] )
3372, 2985, 2H), 7.574 7.50 (m, 2H),
2228, 173 8, calcd for 7.40 — 7,37 (m, 2H), 7.37 —
1649, 1576, C27H25N405, 7.33 (m, 2H), 6.93 — 6.84 (m,
1529, 1504, 485.1819; found, 1H), 5.83 4 5.71 (m, 1H),
1452 4851824 4.617 4.46 (m, 1H), 4.21 (d,
J: 9.3 Hz, 1H), 3.96 (s, 3H),
1.28 (d, .1: 6.] Hz, 3H), 1.13
(d, J: 7.2 Hz, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No, (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8 12.01 (s, 1H), 8,31 (d, J:
8.0 Hz, 1H), 7.98 (d, J: 5.2
Hz, 1H), 7.57 (d, J: 8.1 Hz,
2H), 7.52 (d, ,1: 8.: Hz,
HRMS—ESI W Z)
2H), 7.42 (d, .14 8.3 Hz,
(Thin ?lm) “MM“
2H), 7.39 (d, J: 8.3 Hz,
2984 1739
397 16817 16177 calcd for 2H), 6.87 (d, J: 53 Hz,
i“: 15771 15307 C27H25F(,N205, 1H), 5.90 i 5.82 (m, 1H),
' 1482 7 571.1662; found, 4.59 — 4.48 (m, 1H), 4.22 (d,
571.1671 J: 9.6 Hz, 1H), 3.94 (s, 3H),
1.29 (d, .1: 6.2 Hz, 3H), 1.03
(d, J : 7.2 Hz, 3H).
19F NMR (3 76 MHz, CDClg)
6 -6266, -6269.
1H NMR (400 MHz, CDCl;)
8 12.03 (s, 1H), 8.33 (d, .1:
8.0 Hz, 1H), 8.00 — 7.95 (m,
3H), 7.93 (d, J: 84 Hz,
2H)‘ 7'38 (d’ ‘1 : 8‘? HZ’
SI (m z)
2H)’ 7'35 (d’ J‘ 8‘3 HZ’
(Thin ?lm) +)
2H), 6.86 (d, J: 5.2 Hz,
3364 298]
calcdfor lH),5.86 (dp,.]:9.l,7.1,
h398 171316507
16077 15297 C31H35N209, 6.6 HZ, 1H), 4.60 — 4.50 (m,
1481’ 1418’ 579.2337, found, 1H), 4.35 (qd, J: 7.1, 2.8
1 579.2349 Hz, 4H), 4.22 (d, .1: 9.7 Hz,
1H), 3.93 (s, 3H), 1.37 (t, J:
7.2 Hz, 3H), 1.37 (t,J= 7.1
Hz, 3H), 1.28 (d, .1: 6.2 Hz,
3H), 1.05 (d, J: 7.2 Hz,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS N1VJR
No, (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8 12.10 (s, 1H), 8.34 (d, J:
7.9 Hz, 1H), 7.90 (d, J: 5.2
Hz, 1H), 7.32 (d, J: 8.3 Hz,
HRMS-ESI (m z) 1H), 7.09 (d, J: 87 Hz,
(Thin ?lm) +) 1H), 0.80 (d, .1: 5.3 Hz,
3364, 2939, 1H), 0.85 — 0.80 (m, 3H),
calcd for
1734, 1649, 0.74 (d, J: 2.0 Hz, 1H), 5.88
C27H29C12N2O7,
1488, 1449, (dq, .1: 9.0, 0.2 Hz, 1H),
563.1346, found,
1243 4.83 (d, J: 9.7 Hz, 1H), 4.54
563.13 54
(p, J: 7.2 Hz, 1H), 3.94 (s,
3H), 3.83 (s, 3H), 3.74 (s,
3H), 1.23 (d, J: 0.2 Hz,
3H),1.11(d,J= 7.2 Hz,
1H NMR (400 MHz, CDC13)
8 12.12 (s, 1H), 8.36 (d, J:
7.9 Hz, 1H), 7.90 (d, .1: 5.2
Hz, 1H), 7.32 (dd, J: 8.5,
0.8 Hz, 1H), 7.15 (dd,J=
9.0, 09 Hz, 1H), 0.85 (d, .1:
SI(/1Iz)
(Thin ?lm) 5.2 Hz, 1H), 0.02 — 0,39 (m,
([M+H]+)
3373, 2980, 4H), 5.99 — 5.89 (m, 1H),
1734, 1649, calcd for 4.82 (d, .1: 10.1 Hz, 1H),
1598, 1480, C29H33FZNZO77 4.55 (p, J: 7.2 Hz, 1H), 4.03
1263, 1161, 559.225; found, —3.81(m,7H),1.47(t,J=
1040 559.2258 7.0 Hz, 3H), 1.40 (1, .1: 7.0
Hz, 3H), 1.24 (01, J: 0.1 Hz,
3H), 1.10 (d,.]= 7.2 Hz,
1"’1: NMR (370 MHz, CDC13)
—113.02, -11403.
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. :32; MP IR NMR
No, (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
12.10 (s, 1H), 8,36 (d, .7:
7.9 Hz, 1H), 7.96 (d, J: 5.2
Hz, 1H), 7.29 (d, J: 8.3 Hz,
1H), 7.11 (d, .1: 82 Hz,
. - HRMS-ESI (m z) 1H), 6.85 (d, .1: 5.3 Hz,
g5“ $191310) ([M+H]+) 1H), 6.80 (dd, J: 82,20
’ ’ Hz, 2H), 6.77 (d,J=2.0 Hz,
11:: 1?.35, 1650,4 calcd for
401 2
1;:1576, 4:
1H), 6.70 (d, .14 2.1 Hz,
C29H33C12NZO7,
, ), 5.92 (dq, .1— 102,62_
1243,1147, 591.1659, found,
HZ 1H) 482(d J=100
1041 591.1662
HZ, 1H), 4.62 2 4.47 (m,
1H), 4.03 4 3.81 (m, 7H),
1.47 (t, J: 6.9 Hz, 3H), 1.39
(t, .7: 6.9 Hz, 3H), 1.24 (d, .1
: 6.1 Hz, 3H), 1.12 (d,J:
7.2 Hz, 3H).
'H NMR (400 MHz, CDClg)
512.17(s, 1H), 8.40 (d, J:
7.9 Hz, 1H), 7.96 (d, J: 5.2
Hz, 1H), 7.28 (d, .1 : 7.8 Hz,
1H), 7.13 (d, J: 7.6 Hz,
(Thin ?lm) HRMSEEPSIIfm/Z) 1H), 6.84 (d, J = 5.3 Hz,
([ 1 )
3374, 2976, 1H), 6.70 4 6.50 (m, 4H),
}: 1733, 1649, calcd for 5.96 (dq, J: 10.4, 6.1 Hz,
1527, 1450, C31H39N207, 1H), 4.90 (d, J: 10.2 Hz,
1261,1142, 551.2752; found, 1H), 4.53 (p, .1: 7.2 Hz,
1044 551.2716 1H), 4.05 4 3.80 (m, 7H),
2.26 (s, 3H), 2.22 (s, 3H),
1.47 (t, .1: 7.0 Hz, 3H), 1.39
(t, J: 6.9 Hz, 3H), 1.24 (d, J
= 6.1 Hz, 3H), 1.04 (d, J:
7.2 Hz, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
NIASS
NO, (0C) (cm'l) (1H, 13C1 191:)
1H NMR (400 MHz, CDC13)
612.04(d,./: 0.7 Hz, 1H),
8.31 (d, J: 7.9 Hz, 1H), 7.97
(d, J: 5.2 Hz, 1H), 7.05 —
HRMS-ESI(I112) 6.90 (m, 2H), 6.90 — 6.77 (m,
([M+H]+) 5H), 5.73 (dq, .1: 10.0, 0.1
Hz, 1H), 4.63 — 4.47 (m, 1H),
calcd for
403 3.99 (d,J= 9.9 Hz, 1H), 3.94
C27H2‘JF2NZO7,
(8,314), 3.86 (S, 3H), 3.85 (S,a ,, ’3 ,,
531.1944; found,
3H), 1.26 (d,J— 6.1Hz,
3H), 1.08 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
, -13751.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H, 13C. 191:)
1H NMR (400 MHz. CDC13)
(s,1H),8.35(d,./:
8.0 Hz. 1H), 7.97 (d, J: 5.2
Hz, 1H). 7.20 (d, J: 8.6 Hz.
1H). 7.16 — 7.08 (m, 1H),
6.86 (d, .1: 5.3 Hz. 1H). 6.71
— 6.63 (m, 3H), 6.59 (d, J:
2.8 Hz, 1H), 5.65 (dq. J:
9.9, 6.1 Hz. 1H). 4.61 —4.46
(m, 1H), 4.39 (d, J: 10.0
Wilfg?ff/Z) Hz, 1H), 3.94 (s. 3H), 3.75
.2 (s. 3H), 3.72 (s, 3H). 2.37 (s.
404 : calcd for 3H), 2.30 (s, 3H). 130 (d, J
‘; C29H35N207, = 62 HZ, 3H), 1.09 (d, J:
523.2432; found, 7.2 Hz. 3H).
523.2426
(101MHz,
CDC13)6171.7O, 168.56.
157.82, 157.67. 155.37,
148.74. 140.37. 137.93.
137.69.131.8813134,
130.50. . 128.13,
116.26. 116.08. 111.28,
110.86. 109.41, 75.02, 56.04.
55.08. 47.93. 46.22. 20.36,
.30, 18.82. 17.78.
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No. (CC) (cm'l) (1H. 13C. 191:)
1H NMR (300 MHz. CDC13)
6 12.16 (s. 1H). 8.37 (d. J:
8.0 Hz. 1H). 7.97 (d. J: 5.2
Hz. 1H). 7.32 (d. J: 8.4 Hz.
. HRMS-ESI(7112) 1H). 7.11 (d. .1: 8.4 Hz.
SThm min) ([M+H]+) 1H). 6.85 (d. .1: 5.3 Hz.
3368. 2937. ’5
. 1H). 6.42 — 6.34 (m. 3H).a
2857. 1732. calcd for
405 6.32 (d. J— 2.5 Hz. 1H). 5.884 _
1650. 1609. CZOHMNZOO.
1578. 1529. 555.2337.1ound.M .
. (dq. .14 9.8.6.2 Hz. 1H).
4.82 (d.J—9.9 Hz. 1H). 4.61_
1504 5552.27' 3
—4.46 (m. 1H). 3.94 (s. 3H).
3.82 (s. 3H). 3.75 (s. 3H).
3.74 (s. 3H). 3.73 (s, 3H).
1.23 (d. J: 6.2 Hz. 3H). 1.07
(d. .1: 7.2 Hz. 3H).
1H NMR (300 MHz. CDC13)
8 12.16 (d. .1: 0.6 Hz. 1H).
8.38 (d. .1: 8.0 Hz. 1H). 7.97
(d. J: 5.2 Hz. 1H). 7.30 (d.
= 7.8 7. 0 =
HRMS-ESI(I11Z) J8 l H Plfth37851d§d71L£ 7
(Thin ?lm) ([M4Hr) ‘ Z” )’ ‘ ( "
. 5.3.0.6 Hz. 1H). 9
3373. 2936.
calcd for (m. 5H). 6.57—6.53 (m..
406 1734 1650
1 6‘1 1’ 1577’
C26H35NZO7. 1H). 5.92 (dq. .1: 9.9. 6.2
15291 1‘505’ 523.243 9. found. Hz. 1H). 4.90 (d. J 2 9.9 Hz.
1 523.2437 1H). 4.60 — 4.43 (m. 1H).
3.94 (s. 3H). 3.83 (s. 3H).
3.72 (s. 3H). 2.27 (s, 3H).
2.24 (s. 3H). 1.23 (d. J: 6.2
Hz. 3H). 1.03 (d. .1: 7.2 Hz.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (300 MHz, CDC13)
12.16 (d, J: 0.6 Hz, 1H),
8.38 (d, J: 7.9 Hz, 1H), 7.97
(d, J = 5.2 Hz, 1H), 7.20 (d,
J: 2.2 Hz, 1H), 7.05 (d, J:
HRMS—ESI (m z) 2.2 Hz, 1H), 6.98 4 6.84 (m,
(Thin ?lm) ([M+H]+) 2H), 6.85 (dd, J = 5,4, 0.6
3370, 2937, Hz, 1H), 6.74 (d, J = 8.3 Hz,
calcd for
407 2936, 1734, 1H), 6.64 (d, J: 8.3 Hz,
(1)911ng?0
1650, 1576, 5235433101de 1H), 5.88 (dq, J: 102, 6.1
1528, 1501 523 21429 ’ Hz, 1H), 4.96 (d, J: 10.3
‘ " Hz, 1H), 4.60 4 4.45 (m,
1H), 3.94 (s, 3H), 382 (s,
3H), 3.72 (s, 3H), 2.24 (s,
3H), 2.21 (s, 3H), 1.24 (d, J
: 6.1 Hz, 3H), 1.02 (d, J:
7.2 Hz, 3H).
'H NMR (300 MHz, CDCH)
for both diastereomers of a
1:1 e d12,14(d, J:
0.7 Hz, 1H), 12.07 (d, J: 0.6
Hz, 1H), 8,32 (d, J = 8.6 Hz,
1H), 8.29 (d, J: 8.4 Hz,
1H), 7.98 (d, J: 5.3 Hz,
1H), 7.97 (d, J: 52 Hz,
. HRMS-ESI m/Z 1H), 7.20 4 7.11 (m, 2H),
91““ ?lm) ([M+H]+() )
7.01 4 6.82 (m, 12H), 5.82 4
3368, 2940,
‘63 (m’ 2H)’ 5'04 (d’Ji, i
2839 1736 calcd for
408 1 7 10.1 Hz, 1H), 5.03 (d,J= 9.3
1650, 1577, C27H29F2N2O7, ,
1528, 1478, 531.1937, found,, , Hz, 1H), 4.63 4 4.42 (m,
2H) 3 96 (S 3H) 3 95 (S
1453,1434 531.1942 7 " 7 7
3H), 3.93 (d,J= 2.1 Hz,
3H), 3.90 (d, J: 2.1 Hz,
3H), 3.78 (d, J: 1.8 Hz,
3H), 3.78 (d,J= 1.8 Hz,
3H), 1.37 (d,J= 7.2 Hz,
3H), 1.27 (d, J: 6.2 Hz,
3H), 1.26 (d, J = 62 Hz,
3H), 1.13 (d,J= 7.2 Hz,
v) L11 L10
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (300 MHz, CDC13)
for the major isomer ofa 2:1
mixture ofdiastereomers d
12.09 (d, J: 0.6 Hz, 1H),
8.37 (d, J: 8.0 Hz, 1H), 7.98
. - HRMS'ESU’" Z) (d, .1: 5.2 Hz, 1H), 7.16 (dd,
mm ?lm) ([Mm] ) J = 9.6 2.9 Hz 1H) 6.96
409 3?: 3:2 calcd for (dd, J: 913, 3.2 Hz, 1H),
C27H29F2N207, 6.90 4 6.75 (m, 4H), 6.72 (d,
1 (30’ 1528’
1495’ 1482’ 531.1937, found, J=4.7 Hz, 1H), 5.98—5.79
’ 531.1937 (m, 1H), 4.91 —4.83 (m,
1H), 4.62 4 4.46 (m, 1H),
3.94 (s, 3H), 3.83 (s, 3H),
3.73 (s, 3H), 1.25 (d, J: 6.2
Hz, 3H), 1.11 (d, .1: 7.2 Hz,
[Annotation] an
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
N01 (1H7 13c:1 19F)
1H NMR (300 MHz, CDC13)
for 1:1 mixture of
diastereomers 6 12.20 (s,
1H),12.11(s, 1H), 8.37 (d, J
: 7.8 Hz, 2H), 7.97 (t, J:
.2 Hz, 2H), 7.09 i 6.81 (m,
10H), 6.78 — 6.68 (m, 4H),
.79 — 5,59 (m, 2H), 5.11
(dd, .1: 9.8, 6.2 Hz, 2H),
4.52 (dp, J: 10.0, 71 Hz,
2H), 3.95 (s, 3H), 3,94 (s,
3H), 3.89 (s, 3H), 3.86 (s,
3H), 3.84 (s, 3H), 383 (s,
3H), 3.81 (s, 3H), 3,79 (s,
3H), 3.73 (s, 3H), 3.70 (s,
3H), 1.35 (d, J: 7.2 Hz,
HRMS-ESI (m/Z) 3H), 1.27 (d, J: 4.7 Hz,
([M+H]+) 3H), 1.25 (d, .1 : 47 Hz,
3H), 1.08 (d, J: 7.2 Hz, 3H
calcd for
C29H35N209, 13C NMR (126 MHz,
555.233 7; found,
CDC13) for 1 :1 mixture of
555.23 17
diastereomers 5 171.68,
171.35, , ,
155.31,155.29,152.81,
, 152.74, 152.72,
148.71, 148.67, 147.33,
147.31, 147.15, 147.12,
140.36, 134.98, 13479,
134.67, 134.47, 130.57,
130.50, 123.69, 123.65,
123.62, 121.03, 120.94,
120.41, 120.24, 110.79,
110.57,]10.55,109.35,
109.33, 73.98, 60.39, 60.37,
60.27, 56.07, 56.05, 55.65,
5557,5555, 4792, 47.90,
41.96, 41.92, 18.80, 18.72,
1804, 17.74,
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. n .
:\§» \\\\\ ‘\‘\1 MP
MASS NMR
No, \'\'\x ‘ ~‘ (‘0 (1H7 13c:1 19F)
1H NMR (300 MHz, CDC13)
for 1:1 mixture of
diastereomers 8 12.20 (d, J :
0.5 Hz, 1H), 12.11 (d, J: 0.5
Hz, 1H), 836 (d, J: 7.8 Hz,
2H), 7.98 (dd, .1: 5.9, 5.2
Hz, 2H), 7132(ddd,J= 12.0,
72, 2.1 Hz, 2H), 7.17 — 7.09
(m, 2H), 7.09 4 6.80 (m,
10H), 5.76— 5.57 (m, 2H),
5108(t,J= 9.6 Hz, 2H), 4.59
4 4.41 (m, 2H), 3.96 (s, 3H),
3.94 (s, 3H), 3.83 (s, 3H),
3.79 (s, 3H), 3.69 (s, 3H),
3.68 (s, 3H), 2.36 4 2.19 (m,
HRMS-ESI(/1Iz) 12H), 1.33 41,23 (m, 9H),
([M+H]+) 1.02 (d, J: 7.2 Hz, 3H).
calcd for
411 [73C NMR (126 MHz,
C29H35N2O7,
CDC13) for 1:1 mixture of
523 .243 9; found,
diastereomers 8 171.66,
523 .2409
171.15, 168.48, 168.46,
156.89, 156.80, 156.76,
155.32, 148.74, 148169,
140.38, 140.33, 133.98,
133.84, 133.74, ,
,131.19,131102,
130.98, 130.56, 130.47,
130.09, 130.04, 129177,
129.74, , 126.71,
126.59, 126.34, 123.84,
123.80, , 109.36,
74.58, 74150, 60.29, 60.22,
60.19, 5608, 56.07, 47.89,
4785,4176, 41.70, 19.02,
18.93, 1803,1765, 16.69,
1666, 16.48, 1645.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No. (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
for 1:1 mixture of
diastereomers 6 12.18 (s,
1H), 12.11 (s, 1H), 8.36 (d, J
= 7.9 Hz, 1H), 8.28 (d, J:
7.7 Hz, 1H), 8.06 4 7.91 (m,
2H), 7.11 — 7.00 (m, 4H),
6.95 (t, J: 8.6 Hz, 2H), 6.89
4 6.82 (m, 4H), 6.70 (d, J
8.2 Hz, 2H), 6.65 (dd, J:
80,45 Hz, 2H), 5.70 (ddq, J
: 12.3, 6.1, 3.3, 2.6 Hz, 2H),
4.62 (dd, J: 122,99 Hz,
2H), 4.49 (dp, J: 22.0, 7.2
Hz, 2H), 3.94 (s, 3H), 3.93
(s, 3H), 3.79 (s, 3H), 3.79 (s,
3H), 3.75 (s, 3H), 3.74 (s,
3H), 2.29 (s, 3H), 2.26 (s,
3H), 2.19 (s, 3H), 2.18 (s,
3H), 1.35 — 1.25 (m, 9H),
1.05 (d, J: 7.2 Hz, 3H).
13C NMR (101 MHz,
CDC13) for 1:1 mixture of
reomers 8 171.69,
171.27, 168.52, 157.74,
157.55, 155.32, 148.73,
140.69, 140.38, ,
139.96, 130.52, 126.17,
126.11, 125.90, ,
125.38, 120.47, 120.38,
119.87, 119.66, 109.38,
108.32, 74.97, 74.87, 56.03,
55.46, 55.43, 47.92, 47.89,
47.53, 18.74, 18.72, 17.98,
17.69,11.84,11.74, 11.42.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
812.03 (s, 1H), 8.28 (d, J:
8.0 Hz, 1H), 7.96 (d, J: 5.3
Hz, 1H), 7.05 (ddd, J = 8.4,
.6, 2.2 Hz, 1H), 6.89 — 6.72
(m, 4H), 5.67 (dq, J: 9.6,
6.2 Hz, 1H), 4.86 (d, J = 9.6
Hz, 1H), 4.56 (dt, J: 8.1,
7.0 Hz, 1H), 3.97 (d, .1: 2.4
. Hz, 3H), 3.95 (s, 3H), 3.83
(Thm ?lm) 5
3374, 2941, HRMS—ESI(I112) (/dgé 2%z%)311{)2012615 3d;
1737, 1650, ([M4H]+) ' ‘ "
7 2’ HZ 73H)
1529, 1501, ‘ ’ ‘
calcd for
413 %:;?1 %:§T C27H27F4N207, 13C NMR (126 MHZ,
1263* 1243’ 567,1749,16und, CDC13) 5 , 168.61,
1058 952’ 567.1750 155.43, 148.73, 147.12(d,J
801 ’
: 7.3 Hz), 146.96 (d, .1: 7.6
Hz), 145.26 (d,J: 13.9 Hz),
143.28 (d,J= 13.8 Hz),
140.44, 130.25, 129.70,
129.47, 123.09 (dd, .1: 8.2,
3.8 Hz), 122.45 — 122.20
(111), 110.82 (d,J= 17.3 Hz),
110.57, 109.47, 72.53,
61.22 (d,J:4.1 Hz),61.16
(d, J: 3.6 Hz), 5611,
47.96, 42.46, 18.74, 17.75.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H.13C. 191:)
1H NMR (400 MHz. CDC13)
12.11 (s, 1H), 8.35 ((1.1:
8.0 Hz. 1H), 7.98 (d, J: 5.2
Hz, 1H), 7.11 — 7.00 (m,
3H). 6.94 — 6.84 (m, 4H).
.73 4 5.64 (m, 1H). 4.55 4
. 4.44 (m. 2H), 3.94 (s, 3H).
$212)“ $1212 236 (s, 3H), 2.28 (s, 3H).
1735’ 1550’ HRMS—ESI+(mz) 2.25 (s. 6H), 1.30 (d, .1: 5.1
1576’ 1528’ ([M+H] ) Hz, 3H). 1.03 (d, J = 7.2 Hz.
1 1 3H).
1501,1481, calcd for
1451, 1336, C29H35NZos, 13C NMR (126 MHZ,
1280. 1263, 491.2540. found,
CDC13)5171.84, 168.52.
1212 1145 4912536
1045 801’ 155.34. 148.73, 140.40,
733 ’ . 138.45. 135.47,
, 133.53, 133.33,
130.60, 130.49, 130.27,
128.60, 127.81. 127.27,
126.95, 109.39, 75.10,
56.07, 47.89, 47.34, 21.29,
21.22, 19.79, 19.75, 18.78,
17.66.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
6 12.11 (s, 1H), 8.35 ((1.1:
8.0 Hz, 1H), 7.97 (d, J: 5.2
Hz, 1H), 7.18 (d, J: 7.9 Hz,
1H), 7.12 (d, J: 7.7 Hz,
1H), 6.98 4 6.89 (m, 3H),
6.87 — 6.81 (m, 2H), 5.69
(dq,J= 100,62 Hz, 1H),
. - 45844.48 (m, 1H), 4.45 (d,
$2119“ $191317) J = 10.0 Hz, 1H), 3.94 (s,
1734’ 1649’ HRMSESIfm/z) 3H), 2.35 (s, 3H), 2.29 (s,
([M+H] ) 3H), 2.25 (s, 3H), 2.21 (s,
_, 1576‘ 1527’
1 ‘ 1 3H), 1.30 (d, J: 6.2 Hz,
1500, 1480, calcd for
415 3H) 105 (d J: 7 2Hz
7 ' ‘ a
{ 1450, 1329, C29H35N205,
"51%)'
1280, 1202, 491.2540, found,
1242,1159, 491.2536
13CNMR(126MHZ’
1043, 908,
CDC13)5171.71, 168.51,
799, 728
155.32, , 140.38,
136.43, 136.33, 136.15,
135.95, 135.90, 135.58,
131.50, 131.15, 130.49,
, 127.05, 126.85,
126.58, 109.37, 75.04,
56.06, 47.89, 46.81, 20.84,
.80, 20.12, 20.07, 18.85,
17.71.
ation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8 12.05 (s, 1H), 8,36 (d, J:
8.0 Hz, 1H), 7.98 (d, J: 5.2
Hz, 1H), 7.12 (dd, J: 8.4,
6.0 Hz, 1H), 7.06 — 7.00 (m,
2H), 6.93 4 6.77 (m, 4H),
.60 (dq, J: 9.6, 6.2 Hz,
1H), 4.61 — 4.50(m,1H),
4.48 (d, .1: 9.6 Hz, 1H), 3.94
. (s, 3H), 2.35 (s, 3H), 2.28 (s,
$213)“ $1311; 3H), 1.34 (d, J = 6.2 Hz,
3H)” 1'10 £111] 7‘2 HZ’
1736, 1649, HRMS—ESI (m z)
1576, 1528, ([M+H]+) 3 )‘
32:” $132 calcd for 13C NMR (126 MHz,
1279’ 1263’ C27H29F2N205, CDC13) 8 171.60, 168.60,
1240’ 1184’ 499.2039, found, 161.36 (d, J: 244.0 Hz),
11457 1044’ 499.2035 155.35, 148.72, 140.57 (d, .1
9101803 ’
: 6.5 Hz), [4048, 139.99
7’28 7 (d, J: 6.6 Hz), 132.34 (01, J
= 3.2 Hz), 132.07 (d, J: 7.8
Hz), 132.00 (d, .1: 3.3 Hz),
131.72 (d,J= 7.9 Hz),
130.39, 114.85 (d,J=22.3
Hz), 11432 (d, .1: 22.3 Hz),
113.72 (d,J: 20.7 Hz),
113.42 (d,J= 20.5 Hz),
109.44, 74.21, 56.08,
47.79, 47.70, 19.41, 19.36,
18.76, 17.68.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H. 13C. 191:)
1H NMR (400 MHz. CDC13)
512.07(s. 1H). 8.34 (d. J:
8.0 Hz. 1H). 7.98 (d. J: 5.2
Hz. 1H). 7.01 — 6.90 (m.
2H). 6.88 — 6.80 (m. 3H).
6.71 (ddd. J: 8.9. 3.9. 3.1
Hz, 1H). 6.64 (ddd. J = 8.9.
3.9. 3.1 Hz. 1H). 5.85 (dq, J
: 12.2.6.1 Hz. 1H). 4.70 (d.
J: 10.4 Hz. 1H). 4.61 — 4.52
(Thin ?lm) (m. 1H). 3.94 (s. 3H). 3.74
3367. 2940. HRMS—ESI (m z) (s. 6H). 1.31 (d. .1: 6.1 Hz.
1738. 1650. ([M+H]+) 3H). 1.11 (d. J: 712 Hz.
1530. 1498. 3H).
calcd for
:2“: 1482’ 1453’
C7 H7IF7N7O I“
::~: 1281. 1264. 3177 £6111; "C NMR (126 MHz.
1242.1210. ‘531 11931 ’ CDC13)6171.53. 168.53.
1149. 1037. ' 155.99 (d. J: 24.2 Hz).
802. 730 155,76 4 155.59 (m). 155.32.
154.09 (d,J= 24.6 Hz).
148.70. 140.40. 130.42.
127.85 (d. .1: 15.9 Hz).
127.56 (d,J= 16.3 Hz).
116.26 (d,J= 24.9 Hz).
115.93 (d../: 24.8 Hz).
115.16. 114.19. 11304 (d.J
= 8.2 Hz). 109.39. 72.25.
56.07. 55.69. 47.85. 43.42.
1894. 17.72.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
512.09(s, 1H), 8,34 (d, J:
8.0 Hz, 1H), 7.97 (d, J: 5.2
Hz, 1H), 7.27 (t, J: 8.6 Hz,
1H), 7.16 (t,J= 85 Hz, 1H),
6.86 (d, .1: 5.2 Hz, 1H), 6.64
— 6.54 (m, 3H), 6.47 (dd, J:
12.1, 2.6 Hz, 1H), 5.79 (dq, J
: 12.0, 6.1 Hz, 1H), 4.66 4
4.52 (m, 2H), 3.94 (s, 3H),
(Thin ?lm) 3.75 (s, 3H), 3.72 (s, 3H),
3369, 2938, 1.28 (d, .1: 6.1 Hz, 3H), 1.14
162: i233: (d’ J 7‘2 HZ’ DH)
HRMS-ESI+(m/z)
([M+H] )
1529, 1507, 13C NMR (126 MHz,
1481, 1443, calcd for CDC13) 5 171.55, ,
1320, 1282, C27H26FZNZO7, 161.19 (d, J: 245.6 Hz),
1264, 1242, 531.1937, found, 161.00 (d, J: 2458 Hz),
1195,1154, 531.1933 159.75 (d,J: 11.3 Hz),
1031, 951, 159.47 (d,J= 11.3 Hz),
849, 834, 155.35, 148.69, 140.39,
800, 731 130.42, 129.87 (d, .1: 6.2
Hz), 129.23 (d,J= 5.9 Hz),
119.53 (d,J= 14.6 Hz),
119.33 (d,./: 15.0 Hz),
110.16(d,J=3.0Hz),
109.66 .0 Hz),
109.38, 101.82 (d,./’:26.7
Hz), 101.59 (d, J: 26.6 Hz),
72.49, 56.05, 55.48 (d,J=
6.8 Hz), 47.90, 41.70,
18.91, 17.79.
v) 0 La)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
(s, 1H), 8,34 (d, J:
8.0 Hz, 1H), 7.97 (d, J: 5.2
Hz, 1H), 7.54 (d, J: 7.8 Hz,
1H), 7.30 (d, J: 8.0 Hz,
1H), 7.12 (dd, .1: 7.9, 1.6
Hz, 2H), 7.04 (d, J: 1.8 Hz,
1H), 6.98 (d, J: 1.7 Hz,
$25“ $191211). - 1H), 6.86 (d, .1: 5.2 Hz,
1H), 5.99 (dq, J: 9.5, 6.2
1737’ 1651’ HRMS-ESI (7112) Hz, 1H), 5.00 (d, J: 9.4 Hz,
1616: 1577: ([M+H]+) 1H), 4.5:) 4 4.548 (m, 1H),
"94 (Pm 3‘89 (5’ :H)’
1529, 1454, calcd for
419 3.81
, (s, 3H), 1.26 (d,J— 6.2
1;, 14171 1326, C29H29F6N207,
HZ 3H) 1 05 (d 1: ,7 2H2
1241,1119, 631.1873,f0und, 7‘ 1 ‘;H)“ ‘ 1
1080, 1032, 631.1876 '
905, 860, 13
CNMR(126MHz,
801,738
CDC13)5171,62, 168.58,
157.53, 155.38, ,
140.44, 132.32 ((1, J: 8.6
Hz), 130.37, 130.18,
130.04, 129.47, 125.02,
122.83, 117.30, 116.98,
, 10783410697
(m), 72.18, 56.07, 55.75,
55.69, 47.82, 18.89, 17.66.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz, CDC13)
12.04 (d, J: 0.6 Hz, 1H),
8.34 (d, J: 8.0 Hz, 1H), 7.98
(d, J: 5.2 Hz, 1H), 6.86 (d,
.1: 5.2 Hz,1H),6,65 4 6.52
(Thin ?lm) HRMla‘EESIU’" Z) (m, 4H), 6.45 (ddt, J: 24.3,
(1 1 )
3369, 2940, 10.5, 2.2 Hz, 2H), 5.69 (dq, J
1737, 1592, calcd for = 10.1, 6.1 Hz, 1H),4,61—
1453, 1135, C27H26F2N207, 4.50 (m, 1H), 3.97 4 3.91 (m,
1057, 849, 3 7, found, 4H), 3.77 (s, 3H), 3.75 (s,
730 531.1924 3H), 1.29 4 1.24 (m, 3H),
1.11 (d, .7: 7.2 Hz, 3H).
191: NMR (471 MHz, CDC13)
4110.48 4 —110.65 (m), _
11108 (t, J: 10.0 Hz),
1H NMR (500 MHz, CDCl;)
512,10(s, 1H), 8.35 (d, .1:
8.0 Hz, 1H), 7.98 (d, J: 5.2
Hz, 1H), 6.86 (d, J: 5.2 Hz,
1H), 6.46 4 6.43 (m, 4H),
6.27 (dt, J: 26.6, 2.2 Hz,
2H), 5.75 (dq, J: 10.3, 6.1
Hz, 1H), 4.58 4 4.47 (m,
(Thin ?lm) #:4513155" Z) 1H), 3.94 (s, 3H), 3.89 (d, J
3371, 2938, = 10.5 Hz, 1H), 3.76 (s, 6H),
1735, 1593, calcd for 3.74 (s, 6H), 1.30 4 1.23 (m,
1454, 1204, C29H35N209, 3H), 1.05 (d, J : 7.2 Hz,
1150, 1063, 555.2337, found, 3H).
730 555.2329
13C NMR (126 MHz,
CDC13)6171.70, 168.53,
160.93, 160.75, 155.32,
,143.38,143.10,
140.39, 130.45, 109.36,
106.42, 106.08, 98.42, 98.3 5,
7311,5822, 5606, 55.30,
55.26,47.87,19.21, 17.70.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz, CDC13)
8 12.11 (s, 1H), 8.36 (d, J:
8.0 Hz, 1H), 7.98 (d, .1: 5.2
Hz, 1H), 6.86 (d, J = 5.2 Hz,
1H), 6.69 (dd, .1: 38,18
Hz, 2H), 6.64 (t, .1 : 1.9 Hz,
2H), 6.55 (t, J: 2.0 Hz, 1H),
6.49 (t, J: 1.9 Hz, 1H), 5.75
(dq, .1: 10.5, 6.2 Hz, 1H),
4.58 — 4.48 (m, 1H), 3.94 (s,
. HRMS-ESI (I112) 3H), 3.89 (d, J = 10.5 Hz,
ghm min) ([M+H]+) 1H), 3.76 (s, 3H), 3.73 (s,
1,; 5372, 29.) 7, 5 q
:5 1735, 1594,,
3H), 2.29 (s, 5H), 225 (s,
calcd for
422 3H), 1.25 (d, J — 6.2 Hz,_
,6, 1528, 1452, C29H35N207,
",H) 1 00 (d
1 151, 1065, 523.2439; found, 1 ' I: 7
H) ‘ 1 HZ’
730 523.2434 '
13C NMR (126 MHz,
6171,74, 168.51,
159.74, 159.61, 155.32,
148.70, 142.68, 142.37,
140.40, 139.79, 139.36,
130.47, 121.27, 121.12,
,112.61,111.34,
110.82, 109.36, 73.43, 57.89,
5606,5515, 55.11, 47.86,
21.69,21.61,19.25, 17.66.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No, (cm ) (1H7 13c:1 19F)
1H NMR (500 MHz, CDC13)
8 12.10 (s, 1H), 8.33 (d, .7:
8.0 Hz, 1H), 7.97 (d, ,1: 5.2
Hz, 1H), 7.02 (dd, J: 7.5,
0.9 Hz, 1H), 6.97 (dd, J:
SI (/77 Z) 7.6, 0.8 Hz, 1H), 6.86 (d, .1:
(Thin ?lm)
([M+H]+) 5.2 Hz, 1H), 6.80 (dt,J=
3370, 2937,
7.5, 2.1 Hz, 2H), 6.74 (d,J=
1734, 1649, calcd for
1.6 Hz, 1H), 6.71 (d, .1: 1.6
1528, 1452, C29H35NZO77
Hz, 1H), 5180(dq,J= 10.3,
1260, 1137, 523 .243 9, found,
6.1 Hz, 1H), 4.58 — 4.47 (m,
1039, 729 523 .2434
1H), 3.96 (d, .7: 10.3 Hz,
1H), 3.94 (s, 3H), 3.80 (s,
3H), 3.78 (s, 3H), 2.14 (s,
3H), 2.11 (s, 3H), 1.27 (d, .1
: 6.1 Hz, 3H), 1.00 (d,J:
7.2 Hz, 3H).
lH NMR (500 MHz, CDC13)
512.05(s, 1H), 8.33 (d,J=
8.0 Hz, 1H), 7.98 (d, J: 5.2
Hz, 1H), 7.01 4 6.91 (m,
4H), 6.91— 6.79 (m, 3H),
HRMS-ESI (m ”2) 5.65 (dq, J: 9.6, 6.2 Hz,
(Thin ?lm) ([M+H]+) lH),4.6144.51(m, 1H),
3370, 2938, 3,94 (s, 3H), 3.92 (d, J: 9.7
calcd for
424 1736, 1515, Hz, 1H), 3.85 (s, 3H), 3.83
C27H29F2N2O77
1442, 1275, (s, 3H), 1.24 (d, .1: 6.1 Hz,
531.1937, found,
1216, 731 3H), 1.13 (d,J: 72 Hz,
”P NMR (471 MHz, CDC13)
-134.12(dd,J= 12.1, 8.5
Hz), —134,58 (dd, J: 12.1,
8.7 Hz).
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz, CDC13)
12.13 (d, .7: 0.6 Hz, 1H),
8.36 (d, J: 8.1 Hz, 1H), 7.98
(d,J= 5.1 Hz, 1H), 7.06
(ddd, .1: 9.0, 7.1, 2.4 Hz,
mm ?lm). - HRMS-ESI (m z) 2H), 7.01 (d, .1: 2.0 Hz,
([M+H]+) 2H), 6.86 (d, J: 5.2 Hz,
3370, 2941,
, 1H), 6.72 (d, .1— 8.4 Hz,
1734, 1649, calcd for
425 1H), 6.68 (d, .14 8.4 Hz,,
1503, 1243,, , C29H35NZO7,
, ,
, 1H),5.71(dq,J— 101,61
1135,1033, 52324321611116,
HZ 1H) 4 58 _ 4 48(m3
801, 729 523.2428 1 3 ' '
1H), 3.94 (s, 3H), 3.88 (d, .1
: 10.1 Hz, 1H), 3.77 (s, 3H),
3.74 (s, 3H), 2.16 (s, 3H),
2.12 (s, 3H), 1.24 (d, .1: 6.2
Hz, 3H), 1.03 (d, J: 7.1 Hz,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No, (1H7 13c:1 19F)
1H NMR (500 MHz, CDC13)
12.14 (s, 1H), 8,38 (d, J:
8.0 Hz, 1H), 7.97 (d, J: 5.2
Hz, 1H), 7.05 (d, J: 3.0 Hz,
1H), 6.88 (d, ,1: 3.1 Hz,
1H), 6.85 (d, .1: 5.2 Hz,
1H), 6.77 (d, J: 8.9 Hz,
1H), 6.72 — 6.55 (m, 3H),
.94 (dq, .1: 10.1, 6.1 Hz,
1H), 4.93 (d, J: 10.1 Hz,
HRMS-ESI (m/Z)
(Thin ?lm) 1H), 4.60 — 4.49 (m, 1H),
([M+H]+)
3372, 2940, 3.94 (s, 3H), 3.82 (s, 3H),
1735, 1650, calcd for 3.74 (s, 3H), 3.71 (s, 6H),
1498, 1223, C29H35N209, 1.28 — 1.22 (m, 3H), 1.04 (d,
1047, 804, 555.2337; found, .1: 7.2 Hz, 3H).
730 04
13CN1\4R(1261V1Hz,
CDC13)6 171.72, 168.47,
155.28, , 153.37,
151.78,151.70,148.67,
140.35,130.55,130.51,
116.43, 115.36, 112.05,
112.00,111.68,111.46,
109.31, 627, 56.05,
55.62, 5557,4790, 18.87,
17.81.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz, CDC13)
12.10 (s, 1H), 8.36 (d, J:
8.0 Hz, 1H), 7.97 (d, J: 5.2
Hz, 1H), 7.06 (d, J: 8.4 Hz,
1H), 6.95 (d, ,1: 8.4 Hz,
1H), 6.90 (d, .1: 2.7 Hz,
(Thin ?lm) “11131551,? Z) 1H), 6.86 (d, J: 5.2 Hz,
3370, 2939, 1H), 6.82 (d, J: 2.7 Hz,
1736, 1529, calcd for 1H), 6.66 (dd, .1: 8.4, 2.7
1452, 1243, C29H35N207, HZ, 1H), 6.60 (dd, J: 8.3,
1143, 1043, 523.2439, found, 2.7 Hz, 1H), 5.67 (dq, J:
801, 730 523.2420 10.0, 6.2 Hz, 1H), 4.58 4
4.49 (m, 1H), 4.46 (d, J:
.1 Hz, 1H), 3.94 (s, 3H),
3.74 (s, 3H), 3.73 (s, 3H),
2,34 (s, 3H), 2.26 (s, 3H),
1.32 (d, J: 6.2 Hz, 3H), 1.05
(d, .1: 7.2 Hz, 3H).
1H NMR (400 MHz, CDC13)
(s, 1H), 8.32 (d, J:
7.9 Hz, 1H), 7.98 (d, .1: 5.2
Hz, 1H), 7.43 (dd, J: 8.7,
.6 Hz, 1H), 7.23 (dd, J:
8.7, 5.6 Hz, 1H), 7,1 1 (dd, .1
: 9.6, 2.8 Hz, 1H), 7.04 (dd,
(Thin ?lm) #5151315?” J= 9.6, 2.8 Hz, 1H). 6.96 _
3368, 2933, 6.89 (m, 2H), 6.87 (d, .1: 5.2
1736, 1648, calcd for Hz, 1H), 5.63 (dq, J: 8.7,
1528, 1492, C29H33F2N207, 6.2 Hz, 1H), 4.71 (d, J: 8.8
1481, 1263, 560.2283, found, Hz, 1H), 4.63 (d, .1: 12.4
1094 560.2285 Hz, 1H), 4.58 4 4.36 (m,
4H), 3.94 (s, 3H), 3.43 (s,
3H), 3.38 (s, 3H), 1.30 (d, .1
: 6.2 Hz, 3H), 1.12 (d, .1:
7.2 Hz, 3H).
”P NMR (376 MHz, CDClg)
—115,46, -115,76.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
812.06(s, 1H), 8,33 (d, J:
7.9 Hz, 1H), 7.98 (d, J: 5.2
Hz, 1H), 7.45 (dd, J: 8.7,
.6 Hz, 1H), 7.21 (dd, J:
8.7, 5.6 Hz, 1H), 7. 12 (dd, .1
= 9.6, 2.8 Hz, 1H), 7.07 (dd,
. HRMSESW" Z)
mm ?lm) ([M+H] ) J= 9.7, 2.8 Hz, 1H), 6.94 4
429 1’ .26: 12:71; calcd for 6.84 (m, 3H), 5.73 4 5.56 (m,
1537’ 1481’ C31H37F2N207, 1H), 4.78 4 4.63 (m, 2H),
1262’ 109,; 587.2563, found, 460 4 4.38 (m, 4H), 3.94 (s,
‘ ‘ 587.2559 3H), 3.62 4 3.42 (m, 4H),
1.33 4 1.25 (m, 6H), 123(1,
J: 7.0 Hz, 3H), 1.12 (d, J:
7.2 Hz, 3H).
19F NMR (376 MHz, CDC13)
8 4115.57, 41585.
1H NMR (400 MHz, CDC13)
(s,1H),8,35(d,J=
8.0 Hz, 1H), 7.97 (d, .1: 5.3
Hz, 1H), 7.48 4 7.07 (m, 6H),
HRMSEEPSIIfm/Z) 6.85 (d, J = 5.3 Hz, 1H), 6.58
([ 1 )
(1,7: 8.3 Hz, 2H), 5.85 (dd,
calcd for J: 10.1, 6.0 Hz, 1H), 4.72 -
C26H23FN206, 4.38 (m, 2H), 3.93 (S, 3H),
483.1931; found, 3.83 (s, 3H), 1.25 (d, J: 6.2
483.1928 Hz, 3H), 0.99 (d, J : 7.2 Hz,
”P NMR (3 76 MHz, CDC13)
4113.13.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
CmNE,d. MP 1R NMR
(0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
512.09(s, 1H), 8.33 (d, J:
7.9 Hz, 1H), 7.97 (d, J: 5,2
55???),
Hz, 1H), 7.36 — 7.07 (m, 6H),
6.94 — 6,78 (m, 3H), 5.78
(dq, J: 10.4, 6.1 Hz, 1H),
calcd for 4.52 (p, J: 7.3 Hz, 1H), 4.29
ngHngN205, (d, J: 103 HZ, 1H), 393 (S,
467.1982; found, 3H), 2.39 (s, 3H), 1.28 (d, J
467.1976 = 6.1 Hz, 3H), 1.00 (d, J =
7.2 Hz, 3H).
”P NMR (3 76 MHz, CDC13)
-116.60.
1H NMR (400 MHz, CDC13)
512.09(s, 1H), 8.34 (d, J:
8.0 Hz, 1H), 7.97 (d, .1: 5.2
Hz, 1H), 7.47 — 7.20 (m, 5H),
7.20 — 7.10 (m, 1H), 6.86 (d,
??”, J= 5.2 Hz, 1H), 6.57 (td, J =
8.3, 2.6 Hz, 1H), 6.49 (dd, J
calcd for = 10.9, 2.5 Hz, 1H), 5.83
C26H23FN206, (dq, J: 10.2, 6.1 HZ, 1H),
483.1931; found, 4.61 — 4.49 (m, 2H), 3.94 (8,
483.1931 3H), 3.76 (s, 3H), 1124 (d, J
= 6.1 Hz, 3H), 1.07 (d,J=
7.2 Hz, 3H).
19F NMR (376 MHz, CDC13)
-11349.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
512.07(s, 1H), 8.34 (d, J:
8.0 Hz, 1H), 7.97 (d, .1: 5.2
Hz, 1H), 7.35 (dd, J: 8.7,
.7 Hz, 1H), 7.31 — 7.13 (m,
HRMS-ESI(/11z) 5H), 6.92 — 6.80 (m, 2H),
([M+H]+) 6.76 (dd, J = 9.7, 28 Hz,
1H), 5.75 (dq, J: 10.1, 6.1
C 3163;]?— Hz, 1H), 4.53 (p, .1: 7.3 Hz,
92882, féu?d 1H), 4.26 (d, J: 10.1 Hz,
‘467 11974 * 1H), 3.93 (s, 3H), 2.30 (s,
' 3H), 1.26 (d, .1: 6.1 Hz,
3H), 1.05 (d, J: 7.2 Hz,
”P NMR (3 76 MHz, CDC13)
-116.99.
lH NMR (400 MHz, CDCl;)
12.12 (s, 1H), 8.35 (d,J=
8.0 Hz, 1H), 7.98 (d, J: 5.2
Hz, 1H), 7. 19 (d, .1 : 8.0 Hz,
2H), 7.17 — 7.08 (m, 1H),
#1315535?” 7.01 (d, J = 8.0 Hz, 2H), 6.86
(d, .1: 5.2 Hz, 1H), 6.64 —
calcd for 6.51 (m, 2H), 5.82 (dq, J:
C27H30FN2O6, 9.9, 6.2 Hz, 1H), 4.63 — 4.41
497.2088; found, (m, 2H), 3.94 (s, 3H), 3.83
497.2077 (8, 3H), 2.25 (s, 3H), 1.24 (d,
J: 6.2 Hz, 3H), 1.03 (d,J=
7.2 Hz, 3H),
1"’1: NMR (376 MHz, CDC13)
—113.3 _
v) \1 La)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
“AASS
Nb. 6C) (mn4) CH 13)
?iymy?k(40034Hz.cx)Ch)
812l1(g1}D,834(d“/:
80HL1HL7%M¢J:52
ItJHy7w—7?mmJH)
113mw?=81H12H)700
HRz??f?g"? @??:80HL2H)695—
680(nL3PD,576(dq”/=
calcd for 10.2, 6.2 Hz, 1H). 4.53 (p, J
C27H30FN205, : 7.3 HZ, 1H), 4.25 (d, .l:
48L21391bund, 10211;]fD,393(&3}D,
4812133 238(g3fD,224(&3}D.
127m??:61H;3H)104
(dJ:?2HL3H)
76w?k,CDCh)
—H68O
?JNm?{m00NHh;CDCh)
SQJOQJHLSyde:
80H11H1797QLJ=52
HL]H)7I%7220m1HL
m2H;7mm¢
2HL685QLJ=
Wilfg?ff/Z) 5.2 Hz. 1H). 6.56 (td, J =
83,26P?,“?.648?m?l
calcd for : 10.9. 2.5 Hz. 1H), 5.80
C27H30FN206, (dq, J: 10.4, 6.1 HZ, 1H),
497208&1bun¢ 462—z¥44(nL2PD,394(&
zw7mns 3H)3??g3H)228@
3H)LB(¢J=61HL
3nymu¢1:72H;
wa??KG76NH?,CDCh)
6—H369
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
812.07(s, 1H), 8,33 (d, .7:
8.0 Hz, 1H), 7.97 (d, J: 5.2
Hz, 1H), 7.33 (dd, J: 8.7,
.8 Hz, 1H), 7.18 _ 7.00 (m,
HRMS-ESI(/11z) 4H), 6.94 — 6.81 (m, 2H),
([M+H]+) 6.74 (dd, J = 9.7, 2.8 Hz,
1H), 5.73 (dq, J: 10.1, 6.1
C 61211163131066— Hz, 1H), 4.52 (p, .1: 7.3 Hz,
1315, féudd 1H), 4.22 (d, J: 10.3 Hz,
‘48] 2’12] 3 1H), 3.94 (s, 3H), 2.29 (s,
' 3H), 2.28 (s, 3H), 1.25 (d, .1
: 6.1 Hz, 3H), 1.04 (d, J:
7.2 Hz, 3H).
"’F NMR (3 76 MHz, CDC13)
8 —117.22.
lH NMR (400 MHz, CDClg)
512.09(s, 1H), 8.33 (d,J=
8.0 Hz, 1H), 7.98 (d, J: 5.2
Hz, 1H), 7.31 _ 7.23 (m, 2H),
HRMS-ESI (m/z) 7.12 (dd, J = 8.2, 6.5 Hz,
([M+H]+) 1H), 6.94 — 6.80 (m, 3H),
6.64 _ 6.52 (m, 2H), 5.81
calcd for
438 (dq, J : 10.0, 6.2 Hz, 1H),
501618377f6undH2_F7N706 4.61 — 4.38 (m, 2H), 3.94 (s,
‘501 1829 ° 3H), 3.83 (s, 3H), 1.25 (d, .1
: 6.2 Hz, 3H), 1.06 (d, J:
7.2 Hz, 3H).
”P NMR (3 76 MHz, CDC13)
8 -112.82, -116.36.
ation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
512.08(s, 1H), 8.33 (d, J:
7.9 Hz, 1H), 7.970111: 52
Hz, 1H), 7.33 — 7.12 (m, 3H),
migfglfm‘) 6.97 — 6,83 (m, 5H), 5.73
([ 1 )
(dq, .1: 9.9, 6.1 Hz, 1H),
calcd for 4.68 — 4.46 (m, 1H), 4.28 (d,
C26H2-F2N205, J: 10.1 Hz, 1H), 3.94 (3,
485.1888; found, 3H), 2.36 (s, 3H), 1.28 (d, .1
485.1874 = 6.1 Hz, 3H), 1.09 (d, J:
7.2 Hz, 3H).
”P NMR (3 76 MHz, CDC13)
—115.88, -116.28.
1H NMR (400 MHz, CDC13)
512.08(s, 1H), 8.33 (d,J=
8.0 Hz, 1H), 7.97 (d, .1: 5.2
Hz, 1H), 7.30 _ 7.19 (m, 3H),
6.99 — 6.90 (m, 2H), 6.86 (d,
Wiggly/z)7 J: 5.3 Hz, 1H), 6.57 (td, J=
([ 1 )
8.3, 2.5 Hz, 1H), 6.50 (dd, .1
calcd for = 10.9, 2.5 Hz, 1H), 5.92
C26H2‘F2N2O6, 5.68 (m, 1H), 4.64 — 4.40 (m,
501.1837; found, 2H), 3.94 (s, 3H), 3.76 (s,
501. 1824 3H), 1.23 (d, J : 6.2 Hz,
3H), 1.09 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
-11315, -11603.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
812.06(s, 1H), 8,34 (d, J:
8.0 Hz, 1H), 7% (d, J: 5.2
Hz, 1H), 7.33 (dd, J: 8.7,
.7 Hz, 1H), 7.19 (dd, J:
8.5, 5.4 Hz, 2H), 7.02 4 6.90
W151i??? Z) (m, 2H), 6.91 — 6.82 (m, 2H),
6.77 (dd, J: 9.7, 2.8 Hz,
calcd for 1H), 5.71 (dq, J: 9.8, 6.1
C26H27F2N205, HZ, 1H), 4.53 (p, J = 7.3 HZ,
485.1888; found, 1H), 4.26 (d, J: 9.9 Hz,
485.1876 1H), 3.93 (s, 3H), 2.27 (s,
3H), 1.25 (d, J : 6.2 Hz,
3H), 1.07 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
8 41541—11665.
1H NMR (400 MHz, CDC13)
(s,1H),8,35(d,J=
8.0 Hz, 1H), 7.98 (d, .1: 5.2
Hz, 1H), 7.20 4 7.13 (m,
HRMSfESIXm/Z) 1H), 7.12 4 7.06 (m, 5H),
,(Thm ?lm). ([NHH] ) 7.03 4 6.97 (m, 1H), 6.96 4
calcd for
442 3:2 12:3 6.92 (m, 1H), 6.85 (d, J : 5.2
15767 1529, C27H31N205, HZ, 1H), 579 (dq, J=103,
148 1” [452’ 463.2224; found, 6.1 Hz, 1H), 4.57 4 4.44 (m,
1 ‘ 463.2227 1H), 3.97 (d, J : 10.4 Hz,
1H), 3.93 (s, 3H), 2.31 (s,
3H), 2,27 (s, 3H), 1.25 (d, .1
: 6.1 Hz, 3H), 0.97 (d, J:
7.2 Hz, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
NO, (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8 12.09 (s, 1H), 8,35 (d, .7:
7.7 Hz, 1H), 7.97 (d, .1: 5.2
Hz, 1H), 7.23 (dd, J: 8.5,
6.6 Hz, 1H), 7.17 (dd, J:
8.6, 5.8 Hz, 1H), 6.90 4 6.73
W151i??? Z) (m, 2H), 6.57 (td, J: 8.3, 2.5
Hz, 1H), 6.49 (dd, J: 10.8,
\ calcd for 2.5 Hz, 1H), 5.70 (dq, J:
: C27H29F2N206, 10.1, 6.1 HZ, 2H), 4.75 (d, J
21, found, = 10.2 Hz, 1H), 4.55 (p, J=
516.2018 7.3 Hz, 1H), 3.94 (s, 3H),
3.76 (s, 3H), 2.43 (s, 3H),
1.24 (d, J: 6.2 Hz, 3H), 1.12
(d, .1: 7.2 Hz, 3H).
19F NMR (376 MHz, CDC13)
8 —1]3.36, -11689.
1H NMR (400 MHz, CDC13)
512.07(s, 1H), 8,33 (d, J:
7.9 Hz, 1H), 7.97 (d, .1: 5.2
Hz, 1H), 7.29 (dd, J: 8.4,
6.7 Hz, 1H), 7.25 — 7.14 (m,
1H), 6,86 (d, .1: 5.2 Hz,
1H), 6.81 — 6.70 (m, 2H),
HRMS-ESI (W) 6.56 (td, J: 8.3, 2.5 Hz,
([M+H]+) 1H), 6.50 (dd, .1 : 10.8, 2.5
Hz, 1H), 5.82(dq,J: 11.5,
C 13311;???) 6.2 Hz, 1H), 4.78 (d,J= 10.1
515617237? féurfd Hz, 1H), 4.55 (p, .1: 7.2 Hz,
1H), 3.94 (S, 3H), 3.75 (S,
3H), 1.26 (d, J: 6.1 Hz,
3H), 1.12 (d, ,1: 7.2 Hz,
19F NMR (3 76 MHz, CDC13)
8—112.12(d,J: 7.5 Hz), _
112.18 (d,J= 7.5 Hz), —
112.75
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No1 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
812.08(s, 1H), 8.33 (d, .7:
7.9 Hz, 1H), 7.97 (d, J: 5.2
Hz, 1H), 7.32 (dd, J: 8.6,
.8 Hz, 1H), 7.03 (dd, J:
8.3, 07 Hz, 1H), 6.86 (d, .1:
HRMS-ESI (m/z) 5.2 Hz, 1H), 6.81 (td,J=
+) 8.5, 2.8 Hz, 1H), 6.75 (dd, J
: 9.7, 2.7 Hz, 1H), 6.62 4
calcd for
445 6.51 (111,2H), 5.69 (dq,J=
C27H29F2N206,
.0, 6.2 Hz, 1H), 4.76 (d, J
516.2021; found,
: 9.8 Hz, 1H), 4.53 (p, .7:
16.2021
7.2 Hz, 1H), 3.94 (s, 3H),
3.84 (s, 3H), 2.26 (s, 3H),
1.27 (d, .1: 6.2 Hz, 3H), 1.07
(d, J: 7.2 Hz, 3H).
19F NMR (376 MHz, CDClg)
8 -112.84,_117.29.
1H NMR (400 MHz, CDC13)
812.04(s, 1H), 8.31 (d, .1:
7.8 Hz, 1H), 7.97 (d, J: 5.2
Hz, 1H), 7.32 (dd, J: 8.6,
.7 Hz, 1H), 7.18 4 7.07 (m,
1H), 6.90 — 6.72 (m, 5H),
HRMS-ESI (m/Z)
.70 (dq,J= 11.7, 6.4 Hz,
([M+H]+)
1H), 4.64 (d, .7: 10.0 Hz,
calcd for 1H), 4.54 (p, J: 7.2 Hz,
C26H26F3N205, 1H), 3.94 (s, 3H), 2.27 (s,
504.1821; found, 3H), 1.29 (d, .1: 6.1 Hz,
504. 1818 3H), 1.09 (d, .1: 7.2 Hz,
"’1? NMR (376 MHz, CDClg)
8-111.40(d,J= 7.6 Hz), —
112.58 (d,J= 7.6 Hz), —
116.32.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
CmNE.d. 853,: MP IR NMR
(0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
812.30 4 12.00 (m, 1H),
8.36 (d, .1: 8.0 Hz, 1H), 7.96
(dd, J: 5.2, 1.5 Hz, 1H),
7.39 — 7.12 (m, 6H), 6.89 —
(Thin ?lm) m11§4f18115)m) 6.82 (m, 2H), 6.72 (dd, .1 :
,1“. 3373,2980, 11.3, 1.6 Hz, 1H), 5.82(dq,J
2938, 1737, calcd for = 9.8, 6.0 Hz, 1H), 4.56 (p, J
3:: 1650, 1576, C2(,H28FN205, : 7.3 Hz, 1H), 4.41 (d, .1:
1530, 1481, 77, found, 101 Hz, 1H), 3.92 (s, 3H),
1452 467.1974 223 (s, 3H), 1.26 (d, .1: 6.1
Hz, 3H), 1.09 (d, .1: 7.2 Hz,
19F NMR (376 MHz, CDC13)
8 -11895.
1H NMR (400 MHz, CDC13)
8 1207 (d, .1: 0.6 Hz, 1H),
8.34 (d, .1: 8.0 Hz, 1H), 7.98
(d, J: 5.2 Hz, 1H), 7.29 —
7.23 (m, 2H), 7.21 (t,./: 79
HRMS-ESI (m/z) Hz, 1H), 7.00 — 6.93 (m,
(Thin ?lm)
([M+H]+) 2H), 6.89 — 6.84 (m, 2H),
3377, 2983,
6.75 4 6.71 (m, 1H),5.814
1737, 1650, calcd for
448 5.68 (m, 1H), 4.60 — 4.49 (m,
1577, 1530, C26H2-F2N205,
1H), 4.39 (d, J: 10.1 Hz,
1510, 1481, 485.1883; found,
1H), 3.94 (s, 3H), 2.24 (s,
1453, 1440 485. 1877
3H), 1.26 (d, J: 6.1 Hz,
3H), 1.10 (d,.]= 7.2 Hz,
1"’1: 6 MHz, CDC13)
8 —1 15.56, —118.95.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No. (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
12.10 (s, 1H), 8.36 (d, .7:
8.0 Hz, 1H), 7.97 (d, .1: 5.1
Hz, 1H), 7.28 — 7.12 (m,
3H), 7.08 (d, ,1: 7.8 Hz,
HRMS-ESI (m Z) 2H), 6.88 4 6.81 (m, 2H),
(Thin ?lm)
([M+H]+) 6.71 (d, J: 11.2 Hz,1H),
3378,2982,
.80 (dq,J= 12.1, 6.2 Hz,
2932, 1738, calcd for
449 1H), 4.55 (p, .1: 7.3 Hz,
1650, 1576, C27H30FN2057
1H), 4.38 (d, J: 10.1 Hz,
1530, 1481, 481.2133, found,
1H), 3.92 (s, 3H), 2.28 (s,
1452 33
3H), 2.22 (s, 3H), 1.26 (d, .1
: 6.1 Hz, 3H), 1.09 (d,J:
7.0 Hz, 3H).
"’F NMR (376 MHz, CDC13)
—119.09.
lH NMR (400 MHz, CDC13)
512.09(d,J= 0.6 Hz, 1H),
8.34 (d, J: 8.0 Hz, 1H), 7.98
(d, .1: 5.2 Hz, 1H), 7.24 (dd,
J: 9.4, 5.5 Hz, 1H), 7.15 (t,
HRMS-ESI (m ”2) J: 7.9 Hz, 1H), 6.90 — 6.78
(Thin ?lm) ([M+H]+) (m, 4H), 6.75 4 6.67 (m,
3373, 2982, 1H), 5.79 — 5.68 (m, 1H),
calcd for
450 1737, 1651, 4.64 (d, J: 10.2 Hz, 1H),
C27H29F2N205,
1577, 1530, 4.614 4.52 (m, 1H), 3.94 (s,
499.2039, found,
1482, 1453 3H), 2.39 (s, 3H), 2.24 (s,
499.2033
3H), 1.27 (d, J: 6.2 Hz,
3H), 1.13 (d, .1: 7.2 Hz,
”P NMR (376 MHz, CDCl;)
-1 16.44, -1 18.17.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHZ, CDC13)
(s, 1H), 8,33 (d, J:
. - FIRMS-13810112) 8.0 Hz, 1H), 7.98 (d, .1: 52
5111111111111) ([M+H]+) Hz, 1H), 7.32 — 7.20 (m,
3375,2982,
4 4 2H), 6,9] — 6.70 (m, 5H),
2959, 1759, calcd for
451 5.86 4 5.76 (m, 1H), 4.70 (d,
‘1}; 1651, 1577, C26H26F3N205,
x: J— 10.0 Hz, 1H), 4.62—4.51_
1530, 1504,5 503.1788, found,,
(m’ 1H)’ 3‘94 (5’ 3H)’ 2'254 5
1481 1453 503 1784
‘ ” ‘ " (s, 3H), 1.29 (d, .1: 6.2 Hz,
3H), 1.12 (d, J: 7.3 Hz,
1H NMR (400 MHZ, CDC13)
512.08(d,J= 0.6 Hz, 1H),
8.33 (d, .1: 8.0 Hz, 1H), 7.98
(d, J: 5.2 Hz, 1H), 7.31 _
7.19 (m, 4H), 7.17 — 7.12 (m,
1H)” 7‘ 1 2 'Z'Ozfmgm)’
HRMS—ESI (m z)
+ 6.91 (dd, J7 9.3, 8..) HZ,
([M+H1 )
it: 1H), 6.86 (d, J: 5.2 Hz,
calcd for 1H), 5177(dq, J: 10.2, 6.1
C2(,H28FN205, Hz, 1H), 4.59 -446 (m, 1H),
82; found, 3.99 (d, J: 10.2 Hz, 1H),
467.1969 394 (s, 3H), 2.23 (d, J: 1.9
Hz, 3H), 1.25 (d, .1 : 6.2 Hz,
3H), 0.97 (d, J: 72 Hz,
"’F NMR (3 76 MHz, CDC13)
—120.09.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS NMR
No1 (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
612.08(s, 1H), 8.33 (d, J:
8.0 Hz, 1H), 7.97 (d, J: 5.2
Hz, 1H), 7.25 _ 7.20 (m, 1H),
7.12 - 7.01 (m, 2H), 6.93 -
6.82 (m, 2H), 6.57 (td, .1:
HRMS-ESI(I1IZ)
8.3, 2.5 Hz, 1H), 6.50 (dd, J
([M+H]+)
=10.9,2.5 Hz, 1H), 5.76
calcd for (dq,./: 103,61 Hz, 1H),
C27H29FZNZO65 4.61 — 4.48 (m, 1H), 4.45 (d,
515.1993; found, J: 10.2 Hz, 1H), 3.94 (s,
l 5. 1980 3H), 3.77 (s, 3H), 2.22 (d, .1
:19 Hz, 3H), 1.22 (d, J:
6.1 Hz, 3H), 1.07 (d, J: 7.2
Hz, 3H).
19F NMR (376 MHz, CDC13)
-11333, -12033.
1H NMR (400 MHz, CDC13)
612.10(d,J= 0.6 Hz, 1H),
8.34 (d, .1: 8.0 Hz, 1H), 7.98
(d,J= 5.2 Hz, 1H), 7.31 —
7.27 (m, 2H), 7.24 — 7.15 (m,
4H), 7.15 4 7.06 (m, 3H),
(Thin ?lm)
6.86 (d, J: 5.2 Hz, 1H), 5.81
3373,2980,
(dq,J= 10.2, 6.1 Hz, 1H),
2938,1735 HRMS—ESI (m z)
4.57 4 4.46 (m, 1H), 4.02 (d,
1649,1576, ([M+H]+) J: 10.2 Hz, 1H), 3.94 (s,
1528,1495,
calcd for 3H), 2.28 (s, 3H), 1.26 (d, J
454 1480,1451,
C26H29N205, : 6.1 Hz, 3H), 0.96 (d, .1:
1332,1280,
449.2071; found, 7.2 Hz, 3H).
449.2063
1213,1144, 13CNMR(126 MHz,
1048, 799,
CDC13)6171.68, 168.51,
733, 699
155.33, 148.70, 141.68,
, 138.15, 136.55,
130.48, , 128.48,
127.93, 126.59, 109.38,
73.63, 57.57, 56.07, 47.85,
.98, 19.24, 17.61.
v) 00 La)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R N1er
N0. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
612.11(d,.]: 0.6 Hz, 1H),
8.35 (d, J: 8.0 Hz, 1H), 7.98
(d, J: 5.2 Hz, 1H), 7.29 —
7.24 (m, 4H), 7.20 — 7.15 (m,
3H), 7.03 (d, .1: 7.9 Hz,
2H), 6.86 (d, J: 52 Hz,
(Thin ?lm) 1H), 5.80 (dq, J = 101,62
3367, 2981, Hz, 1H), 4.58 4 4.47 (m,
2938, 1736, 511112351??? Z) 1H), 4.02 (d, J = 100 Hz,
1649, 1576, 1H), 3.94 (s, 3H), 2.25 (s,
1529, 1480, calcd for 3H), 1.25 (d, .1: 6.1 Hz,
1451, 1333, C26H29N205, 3H), 1.01 (d, J : 72 Hz,
1281, 1263, 449.2071, found, 3H).
1213, 1146, 4492068
1048, 801, l3C1\11\4R(1261\4Hz,
734, 700 CDC13) 5 , 168.50,
155.33, 148.69, 141.41,
, 138.28, 136.20,
130.47, , 128.74,
128.05, 127.90, 126.82,
109.36, 73.61, 57.44,
56.06, 47.86, 20.92, 19.23,
17.67.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No. (CC) (cm'l) (1H. 13C. 191:)
1H NMR (400 MHz. CDC13)
512.09(s. 1H). 8.34 (d. J:
8.0 Hz. 1H). 7.98 (d. J: 5.2
Hz. 1H). 7.25 — 7.21 (m.
2H). 7.18 — 7.13 (m. 2H).
7.04 (d. .1: 7.9 Hz. 2H). 7.00
— 6.92 (m. 2H). 6.86 (d. J:
.2 Hz. 1H). 5.75 (dq.J=
$2119“ 210191312). 9.9. 6.2 Hz. 1H). 4.59 4 4.47
1 7
. (m. 1H). 4.02 (d. J: 9.8 Hz.
2957. 1735. HRMS—ESHm/z) 1H) 3.94 (S 3H) 2‘26 (3
1649. 1576. ([M+H] )
3H) 124 (d .1: 6.2 HZ
1528’ 1508’
calcd for 3H). 1.02 (d. J: 7.2 Hz.
456 1480. 1451.
,. C26H23FN205. 3H).
1529. 1280.
467.1977. found._
115;” 1049’126. 1218
'"C NMR (126 MHz.5 74
8151800 ’ CDC13)5171.61. 168.52.
7129 1 161.66 (d. J: 2456 Hz).
155.35. 148.71. 140.40.
138.01. 137.20 .3
HZ). 136.40. 130.44. 129.53
((1. J: 7.9 Hz). 129.22.
127.84. 115.57 (d.J=21.1
Hz).109.39. 73.44. 56.56.
56.07. 47.85. 20.92. 19.14.
17.66.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (300 MHz, CDC13)
6 12.07 (d, J: 0.6 Hz, 1H),
8.33 (d, J: 8.0 Hz, 1H), 7.98
(d, J: 5.2 Hz, 1H), 7.33 —
7.19 (m, 7H), 6.96 — 6,88 (m,
. - 2H), 6.87 (dd, .1: 5.3, 0.6
33713112191812) Hz, 1H), 5.78 (dq, J: 9.9,
2938’ 1736’ 6.1 Hz, 1H), 4.61 — 4.47 (m,
1649’ 1576’ HRMS—ESIEm z) 1H), 4.05 (d, .1: 10.0 Hz,
1529’ 1509’ ([M+H] ) 1H), 3.94 (s, 3H), 1.26 (d, J
1 1
= 6.2 Hz, 3H), 1.05 (d, J:
1480, 1452, calcd for
457 7 2 Hz 3H)
1330, 1280, CgngoFNgOs, ‘ ’ ‘
13331123» WW
1048 815’ ‘ CDC13)6171.62, 16857,
7991732’ 161.59 (d,J:245.2 Hz),
6199 7 155.38, 148.73, 140.92,
140.43, 137.11 (d, 7:35
Hz), 130.39, 129.53 (d,J:
7.8 Hz), 128.88, 127.99,
127.08, 115.29 (d, .1=21.2
Hz), 109.43, 73.50, 57.03,
56.08, 4787, 19.21, 17.69.
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (300 MHz, CDC13)
812.08(d,.]: 0.6 Hz, 1H),
8.33 (d, J: 8.0 Hz, 1H), 7.98
(d, J: 5.2 Hz, 1H), 7.30 —
7.21 (m, 2H), 7.14 (d, J: 8.3
Hz, 2H), 7.09 (d, .1 : 8.2 Hz,
2H), 6.95 — 6.84 (m, 3H),
(Thin ?lm) 5.76 (dq, J: 10.1, 6.1 Hz,
3366, 2979, 1H), 4.59 4 4.47 (m, 1H),
2939, 1736, HRMS-ESI (11272) 4.01 (d, J: 10.1 Hz, 1H),
1649, 1576, ([M+H]+) 3.94 (s, 3H), 2.29 (s, 3H),
1529, 1509, 1.25 (d, .1: 6.1 Hz, 3H), 1.04
C“1 d for
458 1481,1451, (d,J:7.2 Hz, 3H).
4 4 C26H28FN205,
1332’ 1264’
467 1977 found p
1242, 1220, '467 11969 ° 3C NMR (126 MHz,
1159, 1049, ' CDC13) 5 171.61, ,
815, 800, 161.53 (d,J=244.9 Hz),
770, 732 155.37, 148.71, 140.41,
137.93, 137.41 (d,J: 3.3
Hz), 136.72, 130.39,
129.54, 129.4] (d, J: 7.9
Hz), 127.82, 1 15.24 ((1, J:
21.3 Hz), 109.41, 73.55,
56.67, 56.07, 47.87, 20.96,
19.20, 17.68.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
6 12.07 (01, .1: 0.6 Hz, 1H),
8.32 (d, J: 8.0 Hz, 1H), 7.98
(d, J: 5.2 Hz, 1H), 7.35 —
7.20 (m, 5H), 7.19 — 7.10 (m,
1H), 6.88 4 6.75 (m, 3H),
(Thin ?lm) 5.88 — 5.77 (m, 1H), 4.58 —
3376, 2984, 4.47 (m, 1H), 4.42 (d, J:
2938, 1737, 10.1 Hz, 1H), 3.94 (s, 3H),
1649, 1576, £13151??? Z) 129 (d, J = 6.2 Hz, 3H), 1.00
1529, 1503, (d, J: 7.2 Hz, 3H).
1481, 1452, calcd for
459‘ 1~
1327, 1281, F2N205, ”C NMR (126 MHz,
1263, 1243, 471.1726; found, CDC13) 5 171.56, 168.54,
1212,1146, 471.1726 162.05 (dd,./:172.5, 11.9
1050, 966, Hz), 161.09 4 159.28 (m),
849, 800, 155.35, 148.72, 140.42,
733, 699 , 130.41, 130.23 4
[29.63 (m), 128.61, 128.18,
127.03, 12446—12389
(m), 111.63 (d,J= 21.2 Hz),
109.41, 10454410381
(m), 72.76, 56.08, 49.36,
47.83, 18.90, 17.60.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
12.08 (01, J: 0.6 Hz, 1H),
8.33 (d, J: 8.0 Hz, 1H), 7.98
(d, J: 5.2 Hz, 1H), 7.26 —
7.21 (m, 1H), 7.20 — 7.15 (m,
2H), 7.07 4 7.01 (m, 2H),
6.88 — 6.85 (m, 1H), 6.84 —
6.74 (m, 2H), 5.86 — 5.72 (111,
$210“ $9123). 1H), 4.59 4 4.48 (m, 1H),
29371 1737’ 4.39 (d, J: 9.9 Hz, 1H), 3.94
1649’ 1576’ HRMS-ESI (7172) (s, 3H), 2.26 (s, 3H), 1.28 (d,
1 7 +
([M+H] ) .14 6.5 Hz, 5H),i ’3 ’) 1.04 (d, .127
1529 1502
, , 7.2 Hz 3H). ’
460 :b 14%1, 1f52, calcd for
f: 1439, 1329, 59N205, 13C NMR (126 MHZ,
1281, 1264, 485.1885, found,
CDC13)6171,55, 16855,,
1243 121] 485.1880
1147110501 161.99 (dd,J= 171.0, 11.9
966: 8497’ Hz), 160,02 (ch, .1: 170.8,
11.7 Hz), , 148.72,
801, 732
140.41, 136.92, 136.63,
130.43, 12997—12969
(m),129.24, 128.06, 124.73
— 124.42 (m), 111.58 (d,J=
17.7Hz), 109.40, 104.83—
103.37 (m), 72.82, 56.08,
48.91, 47.85, 20.95, 18.90,
17.67.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H,13C, 191:)
1H NMR (400 MHz, CDC13)
5120501.]: 06 Hz, 1H),
8.30 (d, J: 8.0 Hz, 1H), 7.98
(d,J= 5.2 Hz, 1H), 7.31 —
7.17 (m, 3H), 6.97 — 6.75 (m,
. - 5H), 5,835.73 (m, 1H),
$311“ $1913) 4.59 — 4.49 (m, 1H), 4.40 (d,
2939’ 1738’ ,7: 10.0 Hz, 1H), 3.95 (s,
1649, 1604, HRMS—ESI(/1IZ) 3’11}; 1%: Eg’j: 2:111:
1577, 1529, ([M+H]+) ’ ' ‘ ’
\ 3H)
1503’ 1481’ t
calcd for
461 133% i422? C25H24F3N205, 13C NMR (126 MHz,
1264112427 489.1632, found, CDC13)6171.51, 168.59,
1223” 1160’ 4891624 162964 162.09 (m), 161.43
1050* 966’ 4159.21(m), 155.41,
84918107 148.74, 140.45, 135.75,
7132 1 , 129.73 (d,.1:8.0
Hz), 124.13 (dd, J: 15.2,
3.7 Hz), 115.43 (d,J=21.3
Hz), 11173 (d, J: 25.0 Hz),
109.46, 104.30 (t, .1: 25.8
Hz), 72.66, 56.10, 48.70,
47.86, 18.91, 17.67.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
N6. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.28 (d, .1: 5.4 Hz, 1H),
8.14 (d, J: 7.8 Hz, 1H), 7.26
— 7.15 (m, 4H), 6.94 (dddd, J
= 24.3, 8.7, 6.9, 2.1 Hz, 5H),
.76 4 5.63 (m, 3H), 4.55 (p,
J: 7.3 Hz, 1H), 4.05 (d, J:
8.9 Hz, 1H), 3.92 (s, 3H),
2.06 (s, 3H), 1.32 (d, .1: 7.1
HRMS'ESIE’" Z) Hz, 3H), 1.22 (d, J = 6.2 Hz,
([M+H] )
calcd for
462 13
3;, C28H29F2N207, 3C NMR (101 MHZ,
31, found, CDC13) 6 171.92, 170.28,
543.1937. 162.91, 162.81, 162.77,
160.46, 160.37, ,
144.13, 142.28, 136.93,
136.90, 136.54, 136.51,
, 129.74, 129.70,
129.62,115.72,115.51,
115.43, 115.22, 109.60,
89.60, 73.10, 56.20, 55.58,
48.04, 20.85, 20.81, 18.94,
18.05.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.26 (d, .1: 5.4 Hz, 1H),
8.20 (d, J: 7.9 Hz, 1H), 7.28
— 7.17 (m, 4H), 7.02 — 6.89
(m, 5H), 5.76 — 5.66 (m,
3H), 4.55 (p, .1: 7.3 Hz,
1H), 4.04 (d, J: 9.7 Hz,
1H), 3.90 (s, 3H), 2.05 (s,
3H), 1.23 (d, .1: 6.1 Hz,
SIW Z) 3H), 0.99 (d, J: 7.2 Hz,
([M+H] )
calcd for
4637 11
3;, C28H29F2N207, 3C NMR (101 MHZ,
543.1931, found, CDC13) 6 172.24, 170.26,
543.1937. 162.95, 162.90, 162.86,
160.51, 160.42, 160.28,
145.68, 143.98, 142.41,
136.94, 136.91, ,
, 129.62, 129.57,
129.54, 129.49, 115.79,
115.58,115.49,115.28,
109.58, 89.51, 73.04, 56.18,
5613,4805, 20.85, 19.14,
17.81.
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No, (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.26 (d, .1: 5.3 Hz, 1H),
8.21 (d, J: 7.9 Hz, 1H), 7.26
— 7.22 (m, 1H), 7.14 (dd, J:
8.6, 5.8 Hz, 1H), 6.94 (d, .1:
.4 Hz, 1H), 6.89 4 6.77 (m,
4H), 5.73 (s, 2H), 5.62 (dq, J
= 9.7.6.2 Hz, 1H), 4.56 (p, J
: 7.2 Hz, 1H), 4.44 (d, .1:
9.8 Hz, 1H), 3.91 (s, 3H),
2.38 (s, 3H), 2.33 (s, 3H),
2.06 (s, 3H), 1.30 (d, .1: 6.2
Hz, 3H), 1.04 (d, J: 7.2 Hz,
HRMS-ESI (m Z) 13C NMR (101 MHz,
(Thin ?lm) ([M+H]+)
CDC13) 6 172.30, 170.26,
3378, 2984,
calcd for 162.91, 161.19 (d, .1: 245.6
464 1738, 1676,
C30H33F2N207, Hz), 161.10 (d,J: 2450
1496, 1202,
571.2250; found, Hz), 160.28, 145.70, 143.98,
1003, 729
571.2265 142.43, 139.12 (d, .1: 7.4
Hz), 138.81 (d, .1: 7.5 Hz),
134.89 (d,J= 3.3 Hz),
134.39 (d, J: 3.2 Hz),
12937 (d, .1: 8.2 Hz),
128.75 (d,J= 8.3 Hz),
117.41 (d,J= 20.9 Hz),
117.10 (d, J: 20.9 Hz),
112.94 (CLJ: 20.9 Hz),
112.63 (d,J= 20.8 Hz),
, 8952,7429, 5619,
4807, 4640,2086, 2020,
.12,18.82,17.86.
"’F NMR (376 MHz, CDC13)
-116.57, —117.03.
v) 0 La)
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.26 (d, .1: 5.4 Hz, 1H),
8.23 (d, J: 7.8 Hz, 1H), 7.32
— 7.20 (m, 8H), 6.93 (d, J:
.4 Hz, 1H), 5.79 (dq, J:
.2, 6.1 Hz, 1H), 5.73 i
.70 (m, 2H), 4.50 (p, J: 7.2
Hz, 1H), 3.98 (d, J: 10.2
HRMS-ESI (m z) Hz, 1H), 3.89 (s, 3H), 2.05
(Thin ?lm) ([M+H]+) (s, 3H), 1.27 — 1.22 (m,
3379, 2962, 21H), 0.78 (d, J: 7.2 Hz,
calcd for
465 2:; 1 73 7, 1676, 3H).
\ C36H47NZO77
‘ 1158821172591, 61933781 found 13C NMR
1 ( 101 MHz
619.3388 ’
CDC13) 6 172.43, 170.23,
162.84, 160.24, 149.56,
149.37, 145.69, ,
142.62, 138.80, 138.26,
127.69, 127.65, 125.60,
125.33, 109.49, 89.55, 73.71,
5725,5615, 4804, 34.36,
34.31, 31.30, 20.85, 19.34,
17.50.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No, (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.26 (d, .1: 5.4 Hz, 1H),
8.22 (d, J: 7.8 Hz, 1H), 7.28
— 7.19 (m, 4H), 7.16 — 7.06
(m, 4H), 6.93 (d, J: 5.4 Hz,
1H), 5.78 (dq, .1: 10.2, 6.1
Hz, 1H), 5.72 (d, J: 0.9 Hz,
2H), 4.51 (p, J: 7.2 Hz,
1H), 3.98 (d, .1: 10.2 Hz,
1H), 3.89 (s, 3H), 2.81 (dh, J
(Thin ?lm) Wilfg?ff/Z) = 10.6, 6.9 Hz, 2H), 2.05 (s,
3378, 2959, 3H), 1.24 (d, .1: 6.1 Hz,
1737, 1676, calcd for 3H), 1.18 (dd, J : 13.6, 6.9
1506, 1202, C34H43NZO7, Hz, 12H), 0.81 (d, J: 7.2
1044, 1004, 591.3065; found, Hz, 3H).
828, 731 77
13CN1\4R(1011V1Hz,
CDC13)6 172.42, 170.24,
162.85, 160.24, 147.29,
147.13, , 143.92,
142.63,139.19,138.71,
127.95, 127.92, 126.75,
126.48, 109.49, 89.55, 73.66,
57.39, 5616,4805, 33.65,
33.61, 23.99, 23.97, 23.93,
.86, 19.33, 17.57.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd.
MASS N1VJR
No1 (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.27 (d, .1: 5.3 Hz, 1H),
8.23 (d, J: 7.8 Hz, 1H), 7.07
— 6.90 (m, 7H), 5.82 — 5.67
(m, 3H), 4.54 (p, J: 7.2 Hz,
1H), 3.90 (s, 3H), 2. 17 (t, .1:
11.4 Hz, 12H), 2.06 (s, 3H),
FIRMS-13810772) 1.28 — 1.20 (m, 4H), 0.93 (d,
(Thin ?lm)
([M+H]+) .1: 7.2 Hz, 3H).
3388, 2979,
1756, 1677, calcd for
467 13C NMR (101 MHz,
1503, 1203, C32H39N207,
CDC13) 5 172.41, 170.25,
1044, 1004, 563.2752, found,
162.84, 160.23, 145.69,
970, 731 64
143.90, 142.67, 139.25,
139.11, 136.78, 136.34,
134.93, 134.51, 129.90,
129.62, 129.39, 129.38,
125.30, 125.08, 109.48,
89.55, 73.49, 57.1 1, 56.16,
4812,2086, 19.87, 19.80,
19.32, 1929,1924, 17.80.
1HNMR (400 MHz, CDC13)
8.41 (d, J: 7.7 Hz, 1H),
8.30 (61, .1: 5.4 Hz, 1H), 7.32
— 7.21 (m, 1H), 7.14 (dd,J=
8.5, 5.8 Hz, 1H), 6.99 (d,J=
.5 Hz, 1H), 6.83 (ddd,./:
.6, 10.1, 7.6 Hz, 4H), 5.62
ESIMS 777 Z 541.2
:57?”Haw/[J (dq, J = 9.6, 6.1 Hz, 1H),
468 ([M+H]+) 4.62 4 4.50 (m, 1H), 4.43 (d,
, J: 9.7 Hz, 1H), 3.88 (s, 3H),
2.38 (s, 3H), 2.36 (s, 3H),
2.31 (s, 3H), 1.29 (d, .1: 6.2
Hz, 3H), 1.03 (d, .1 : 7.2 Hz,
”P NMR (376 MHz, CDCH)
2, -11696.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.43 (d, .1: 7.9 Hz, 1H),
8.32 (d, J: 5.4 Hz, 111), 7,26
(d, J: 12.1 Hz, 8H), 6.98 (d,
.1: 5.4 Hz, 1H), 5.78 (dq, .1:
.1, 6.1 Hz, 1H), 4.56 4
4.43 (m, 1H), 3.97 (d, J =
HRMS—ESI(7172) 1337512” 1:11) j i: (3’ 3,11)”‘3 (5’ " )’ ' ( " 7
(Thin ?lm) ([M+H]+) 12.6 Hz, 21H), 0.77 (d, J:
3379, 2962,,
calcd for 7.2 Hz, 3H).2
469 1772, 1677,
C35H45N20‘”
1508 1 198 1
71,1 1 589.3272; found, 1”C NMR (101 MHz,
589.3289 6172.32, 168.88,
162.23, 159.40, 149.55,
149.37, 146.64, 141.60,
138.76, 138.25, 137.43,
127.70, 127.65, 125.60,
125.32, 109.67, 73.75, 57.22,
56.25, 47.81, 34.35, 34.31,
3131,3130, 2073,1932,
17.69.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No, (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.42 (d, .1: 7.6 Hz, 1H),
8.32 (d, .1: 5.5 Hz, 1H), 7.22
(dd, J: 8.3, 2.5 Hz, 4H),
7.15 4 7.04 (m, 4H), 6.98 (d,
.1: 5.5 Hz, 1H), 5.78 (dq,.1:
.1, 6.1 Hz, 1H), 4.54 4
4.43 (n1, 1H), 3.97 (d, J:
.2 Hz, 1H), 3.89 (s, 3H),
HRMS-ESI (m z) 2.82 (dp, J: 11.9, 6.9 Hz,
(Thin ?lm)
+) 2H), 2.37 (s, 3H), 1.23 (d, J
3379, 2960,
: 6.2 Hz, 3H), 1.18 (dd, J:
1772, 1677, calcd for
470 14.7, 6.9 Hz, 12H), 0.80 (d, J
1509, 1201, C33H41N206,
= 7.2 Hz, 3H).
1175, 1047, 561.2959; found,
73 1 561.2977
13C NMR (101 MHz,
CDC13)6172.31, 168.89,
162.23, 159.41, 147.28,
147.13,146,64,141.61,
139.14, 138.70, 137.43,
127.96, 127.92, 126.75,
126.47, 109.68, 73.70, 57.36,
56.25, 4783, 33.64, 33.61,
23.97, 074, 19.31,
17.75.
1H NMR (400 MHZ, CDC13)
8 8.48 4 8.37 (m, 1H), 8.32
(Thin ?lm) SI (m Z)
(d, J: 5.4 Hz, 1H), 7.09 4
3379, 2978, ([M+H1+) 6.90 (n1, 7H), 5.74 (dq, J:
1771, 1676,
calcd for 10.0, 6.1 Hz, 1H), 4.58 4
471 1505, 1450,
C31H37N2067 4.46 (m, 1H), 3.98 4 3.83 (m,
1310, 1199,
533.2646, found, 4H), 2.38 (s, 3H), 2.17 (dd, J
1050, 907,
533.2659 = 12.4, 11.0 Hz, 12H), 1.22
(d, .1: 6.1 Hz, 3H), 0.92 (d,
J: 7.1 Hz, 3H).
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.26 (d, .1: 5.4 Hz, 1H),
8.22 (d, J: 7.9 Hz, 1H), 7.38
HRMS-ESI (m/Z) (m, 1H), 7.13 (m, 1H), 6.94
([M+H], ) (d, J = 5.4 Hz, 1H), 6.61 _
(Thin ?lm) i
M . 6.47 (m, 4H), 5.87 (dq, .14
3382, 2982, calcd for
, 9.7, 6.2 Hz, 1H), 5.72 (s,
1737, 1677, F2N209,
1501, 1202 603.2149, found,2 _ 2H), 4.84 (d, J— 9.6 Hz,
1H), 46444.48 (m, 1H),
60, 216,3' 3
3.90 (s, 3H), 3.82 (s, 3H),
3.74 (s, 3H), 2.06 (s, 3H),
1.22 (61, .1: 6.2 Hz, 3H), 1.03
(d, J : 7.2 Hz, 3H).
1H NMR (400 MHz, CDC13)
HRMS-ESI(/1Iz) 5 8,77 , 8.42 (m, 1H), 8.42 ,
(Thin ?lm) ([M+H]+) 8.15 (m, 1H), 7.26 4 7.15 (m,
3367, 2985, 4H), 7.06 4 6.86 (m, 5H),
C2110d for
473 1749,1694, 5.844566 (m, 3H), 5.374
C H RN 0
1506, 1201, ”$816225? 13111121 5.19 (m, 1H), 4.13 44.03 (m,
1130, 828 1H), 4.04 4 3.83 (m, 3H),
597.1672
2.09 4 1.99 (m, 3H), 1.30 4
1.16 (m, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (300 MHz, CDC13)
8.28 (t, .1: 7.2 Hz, 2H),
7.35 — 7.12 (m, 10H), 6.94
(d, J: 5.4 Hz, 1H), 5.86 (q,
.]= 6.3 Hz, 1H), 5.75 — 5.68
(m, 2H), 4.62 (p, .1: 7.2 Hz,
1H), 3.90 (s, 3H), 2,06 (s,
Wilfg?fy/Z) 3H), 1.75 (s, 3H), 1.16 (d, J
: 6.3 Hz, 3H), 1.12 (d, .1:
calcd for 72 Hz, 3H).
C29H33N207,
521.2282; found, ”C NMR (101 MHz,
521.2292, CDC13) 5 172.27, 170.20,
162.88, 160.26, 146.57,
145.66,145.11,143.98,
142.56, 128.18, 128.09,
127.92, 127.40, ,
126.11, 109.53, 89.54, 75.94,
56.17, 50.41, 48.23, 23.95,
.84,18.13,15.97.
'H NMR (400 MHz, CDCH)
6 8.41 (d, J: 4.6 Hz, 1H),
8.31 (d, J: 5.4 Hz, 1H), 7.37
(dd, .1: 8.5, 6.7 Hz, 1H),
. 7.12(dd,J:8.3, 6.7 Hz,
$319“ £19123 HRMS-ESIfm/z) 1H), 6.99 (d, J = 5.5 Hz,
1769’ 1736’ ([M+H] ) 1H), 6.63 4 6.44 (m, 4H),
* ’ 5.86 (dq, J: 9.5, 6.2 Hz,
1677, 1598, calcd for
475 :3; 1H), 4.83 (d, J — 9.5 Hz,_
1500, 1277, C29H31F2N203,
1H) 4 62 2 4 45 (m” 1H)
1192,1174, 573.2043;f0und, ', g ’, ”
"90(31 JH)’ 382(5’ 3H)?,
1151 1033 573 2055
9’53 7 ' 3.73 (s, 3H), 2.38 (s, 3H),
1.21 (d, J: 6.2 Hz, 3H), 1.01
(d, .1: 7.2 Hz, 3H).
191: NMR (376 MHz, CDC13)
8 -113.49,_113.81.
[Annotation] an
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd. MP 1R NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1:1 mixture of diastereomers.
. H NMR (500 MHz CDC13),
(Thm ?lm) ’
8,52 2 8.46 (m, 1H), 8.20
33827 3028, HRMS-ESI W Z)
+ (d,J— 7.6 Hz, 1H), 8.16(d,
2984’ 1736’ ([M+H] ) J: 7.5 Hz, 1H), 7.33 — 7.10
476 1161;? 1:2: calcd for (m, 11H), 5.86 , 5.74 (m,
1310’ 1261’ C28H31N207, 3H), 4.61 — 4.48 (m, 1H),
104; 967* 507.2126; found, 410 — 4.04 (m, 1H), 4.02 (3,
91031825 5072141 3H), 2.06 (s, 3H), 2.05 (s,
728’ 703’ 3H), 1.31 (d, J: 7.1 Hz,
1 3H), 1.28 — 1.20 (m, 3H),
0.91 (d, J: 7.2 Hz, 3H).
1H NMR (400 MHz, CDC13)
8.30 (d, .1: 5.5 Hz, 1H),
FEMS-E8199 7‘%0§d2éi%’%i125”1354( _ )1 _
(Thin ?lm) ([M+H]+) '3
’ Z’ ‘
7.30 (m, 4H), 7.03 (d, J: 5.5
”76 2985
477 3328’ 176‘9’ calcd for Hz, 1H), 5.76 (dq, J: 8.8,
17,8” 1674’ C29H2-N4O6, 6.1 Hz, 1H), 4.60 — 4.52 (m,
31505 1 527.1925, found, 1H), 4.20 (d, J: 9.0 Hz,
527.1931 1H), 3.95 (d, .1: 9.9 Hz,
1H), 3.92 (s, 3H), 2.39 (s,
3H), 1.25 (d, J: 6.2 Hz,
3H), 1.08 (d, .1: 7.2 Hz, 3H)
1H NMR (400 MHz, CDC13)
8.38 (d, J: 7.9 Hz, 1H),
FIRMS-138101272) 812 7 8'29 (m’ 1H)” 7'56 (9’
. + J— 7.9 Hz, 2H), 7.52 (d,J—
$317113? ([M+H] ) 8.5 Hz, 2H), 7.44 4 7.36 (m,
calcd for 4H), 7.01 (dd, J: 5.5, 3,5
478 17727 17397
CZQHZ'FGNZOG, Hz, 1H), 5.88 — 5.79 (m,
1677, 1617,
613.1768; found, 1H), 4.59 — 4.53 (m, 1H),
()13. 178 4.22 (d, .1: 9.2 Hz, 1H), 3.90
(s, 3H), 2.38 (s, 3H), 1.28 —
1.22 (m, 3H), 0.98 (d, J = 7.2
Hz, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.38 (d, .1: 8.7 Hz, 1H),
8.32 4 8.29 (m, 1H), 79701,
J: 8.3 Hz, 2H), 7.93 (d, J:
HRMS-ESI(717Z) 8.2 Hz, 2H), 7.38 (d, .1: 8.3
([M+H] ) Hz, 2H), 7.34 ’) : 8.4 Hz,
(Thin ?lm)
2H), 7.00 (d, J— 5.5 Hz,
3379, 2980, calcd for
479 1H), 5.85 (dq, J— 9.6, 6.1_
1772, 1714, C33H37N2016,
,, . ,4.5944.50(m,
1678, 1508 621.2443,16und,
1H), 4.38—4.30(m,4H),, ,
6212451'
4.21 (d, J: 9.7 Hz, 1H), 3.89
(s, 3H), 2.38 (s, 3H), 1.36 (t,
J: 7.3 Hz, 6H), 1.25 (d, J:
6.3 Hz, 3H), 0.98 (d, J: 7.1
Hz, 3H).
1H NMR (400 MHz, CDC13)
8.28 4 8,24 (m, 1H), 8.20
(d, .1: 7.8 Hz, 1H), 8.00 4
7.92 (m, 4H), 7.42 — 7.31 (m,
Wiggly/Z),7 4H), 6.95 (d, J = 5.4 Hz,
([ 1 )
(Thin ?lm) 1H), 5.85 (dp, .1 : 9.4, 7.2,
3379, 2983, calcd for 6.6 Hz, 1H), 5.73 — 5.67 (m,
1714, 1676, C34H36N2011, 2H), 4.56 (p, J: 6.9 Hz,
1607, 1507 651.2548; found, 1H), 4.39 4 4.28 (m, 4H),
651.2560 422 (d,J: 9.7 Hz, 1H), 3.91
(d, J: 1.5 Hz, 3H), 2.06 (s,
3H), 1.37 (t, J: 7.2 Hz, 6H),
1.27 (d, J: 6.2 Hz, 3H), 0.98
(d, J = 7.1 Hz, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd.
MASS NMR
No, (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.26 (d, .1: 5.4 Hz, 1H),
8.22 (d, J: 7.9 Hz, 1H), 7.34
(d,J= 8.3 Hz, 1H), 7.09 (d,
.1: 8.0 Hz. 1H), 6.94 (11.1:
.4 Hz, 1H), 6.88 4 6.82 (m,
(Thin ?lm) HRMS-ESI(/1Iz)
2H), 6.81 (s, 1H), 6.76 (d, J
4,“ 3379, 2939,
= 2.0 Hz, 1H), 5.86 (dq, J:
([M+Na]_) calcd for
481 .,,.”,1, 1737, 1677, C30H32C12N2N309,
,,(lg/1...,
, 9.7, 6.2 Hz, 1H), 5.72 (s,
, , 1490, 1247, 657.1377, found,
, 2H), 4.84 (d, .1: 9.6 Hz,
1202, 1033 657.1387
1H), 4.57 (p, J: 7.2 Hz,
1H), 3.90 (s, 3H), 3.83 (s,
3H), 3.74 (s, 3H), 2.06 (s,
3H), 1.22 (d, J: 6.2 Hz,
3H), 1.04 (d, .1: 7.2 Hz,
1H NMR (400 MHz, CDCH)
6 825 (1, .1: 6.6 Hz, 2H),
7.34 (dd, J: 85,69 Hz,
1H), 7.13 (111,7: 79,67,
4.7 Hz, 1H), 6.93 (d, .1: 5.4
Hz, 1H), 6.60 — 6.36 (m,
HRMS-ESI (m/Z)
(Thin ?lm) 4H), 5.90 (dq, J= 102,62
([M+H]+)
3380, 2981, Hz, 1H), 5.73 (s, 2H), 4.83
1736, 1677, calcd for (d, J: 10.1 Hz, 1H), 4.63 —
1597, 1500, C32H3‘F2N209, 4.48 (m, 1H), 4.08 — 3.79 (m,
1274, 1202, 631.2462; found, 7H), 2.06 (s, 3H), 1.47 (1, .1:
1003 63 1.2461 6.9 Hz, 3H), 1.40 (1, J : 6.9
Hz, 3H), 1.23 (d, J: 6.2 Hz,
3H), 1.04 (d, .1: 7.2 Hz,
”P NMR (376 MHz, CDCl;)
8 -113.76,-114.20.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.29 4 8.19 (m, 2H), 7.31
(d, J: 8.3 Hz, 1H), 7.11 (d,
J: 8.2 Hz, 1H), 6.94 (d, J:
- HRMS-ESI m ]+() ) 5.4 Hz, 1H 6.86 — 6.73
, m,
ghm ?lm) 3H), 6.72)(d, .1: 2.0 Hz,
”38129801 1H), 5.89 (dq, J= 99,62
1736’ 1677’ cam for
483 Hz, 1H), 5.73 (s, 2H), 4.83
1591,1491, C32H37C12N209,
(d 1:98HZ 1H) 457(
1247,1201, 663.1871; found, J;7 2H2 1H) 4 (1)5;3 $31
1040 6611877
(m, 7H), 2.06 (s, 3H), 1.47 (t,
J: 6.9 Hz, 3H), 1.39 (t, J:
6.9 Hz, 3H), 1.23 (d, J : 6.1
Hz, 3H), 1.06 (d, J: 7.2 Hz,
1H NMR (400 MHz, CDC13)
8.29 4 8.18 (m, 2H), 7.30
(d, .1: 7.8 Hz, 1H), 7.13 (d,
J: 7.7 Hz, 1H), 6.92 (d, J:
.4 Hz, 1H), 6.67 — 6.57 (m,
mm ?lm). - HRMS'ESU'" Z) 3H), 6.54 (s, 1H), 5.93 (dq, .1
([Mm] ) = 10.3, 6.1 Hz, 1H), 5.72 (s,
484 $22133: calcd for 1H), 5.72 (s, 1H), 4.90 (d, J
16761 15047 C34H43N2‘OI), : 10.1 HZ, 1H), 4.55 (13, J:
12001 1043’ 623.2963; found, 71 Hz, 1H), 4.04 — 3.81 (m,
1 623.2962 7H), 2.26 (s, 3H), 2.23 (s,
3H), 2.05 (d, .1: 1.8 Hz,
3H), 1.47 (t, J: 7.0 Hz, 3H),
1.39 (t, J: 7.0 Hz, 3H), 1.23
(d, J: 6.] Hz, 3H), 0.99 (d,
J : 7.2 Hz, 3H).
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd.
MASS NMR
No. (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz. CDC13)
8.39 (d, .1: 6.9 Hz.1H).
8.29 (d. .1: 5.4 Hz. 1H), 7.05
— 6.92 (m. 3H), 6.89 (dd, J:
8.1. 2.1 Hz. 1H). 6182 (dddd.
HRMS-ESI (/17 Z)
.1: 15.8. 8.3. 4.0. 2.1 Hz.
([M+H]+)
3H). 5.72 (dq,J= 9.7, 6.1
calcd for Hz. 1H). 4.65 — 4.48 (m. 1H).
C29H31F2N208, 3.99 (c1. .1: 9.8 Hz. 1H). 3.88
573 .205 1; found, (s, 3H). 3185 (s, 6H). 2.38 (s.
573 .2044 3H). 1.24 (d. J: 6.1Hz,
3H). 1.02 (61.7: 7.1 Hz,
19F NMR (376 MHz,CDC13)
8 -13720, -13768.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No. (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz. CDC13)
8.43 (d. .1: 7.8 Hz. 1H).
8.28 (d. J: 5.4 Hz. 1H). 7,21
(d.J= 8.5 Hz. 1H). 7.17 —
7.09 (m. 1H). 6.96 (d. .]= 5.5
Hz. 1H). 6.79 - 6.57 (m. 4H).
.63 (dq. J: 9.7. 6.1 Hz.
1H). 4.64 — 4.50 (m. 1H).
4.38 (d. .1: 9.9 Hz. 1H). 3.86
(s. 3H). 3.73 (s. 3H). 3.71 (s.
SI (m/Z)
3H). 2.38 (s. 3H). 2.35 (s.
([M+H]+)
3H). 2.31 (s. 3H). 1.29 (d. .1
calcd for :61 Hz. 3H). 1.01 (61.1:
C31H3‘N208, 7.1 Hz. 3H).
565.2542; found.
13C NMR (101 MHz.
CDC13)6172.25. 168.81.
162.28. 159.43. .
157.67. 146.63. 141.55.
137.98. 137.71. 137.44.
131.95.131.46.128.85.
128.22. 116.24. 116.03.
111.25. 110.94. 109.75.
74.80. 56.24. 55.05. 47.92.
46.23. 20.71. 20.36. 20.28.
18.88.1808.
1HNMR (400 MHz. CDC13)
8.26 (d.J: 5.4 Hz. 1H).
8.21 (d. J: 7.8 Hz. 1H). 7.06
_ 6.92 (m. 3H). 6.92 _ 6.74
HRMS-ESI (m 2)
(m. 4H). 5.84 _ 5.61 (m. 3H).
([M+H]+) 4.56 (p. J: 7.3 Hz. 1H). 4.00
calcd for (d.J= 9.8 Hz. 1H). 3.91 (s.
C30H33FZNZO‘L 3H). 3.86 (s. 6H). 2.06 (s.
603.2157; found. 3H). 1.25 (d. J: 6.2 Hz.
603 .2150 3H). 1.02 (d. J: 7.2 Hz.
191: NMR (376 MHz. CDC13)
8 -13720. -137.72.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H. 13C. 191:)
1H NMR (500 MHz. CDC13)
8.44 (s. 1H). 8.31 (01.7:
.4 Hz. 1H). 7.33 ((1.1: 8,5
,, Hz. 1H). 7.10 (d. J: 8.4 Hz.
(Thin ?lm) W151i???) 1H). 6.98 (d. .1: 5.5 Hz.
3383. 2938. 1H). 0.42 4 0.34 (m. 4H).
2837. 1770. calcd for 5.85 (dq. J: 9.7. 0.2 Hz.
1733. 1077. C31H34N20m. 1H). 4.81 (d. J: 9.8 Hz.
1009. 1580. 597.2443; found. 1H). 4.59 4 4.49 (m. 1H).
1505. 1453 597.2438 3.90 (s. 3H). 3.82 (s. 3H).
3.75 (s. 3H). 3.74 (s. 3H).
3.73 (s. 3H). 2.38 (s. 3H).
1.21 (d. J : 0.2 Hz. 3H). 0.99
(d. J: 7.2 Hz. 3H).
1H NMR (500 MHz. CDC13)
8.44 (s. 1H). 8.31 (d, J:
.4 Hz. 1H). 7.31 (d. .1: 7.7
Hz. 1H). 710(01. ./:8.1 Hz.
1H). 0.98 (d. J— 5.5 Hz.
HRMSESI (m/Z)
1H). 0.09 4 0.05 (m. 1H).
(Thin ?lm) ([M+H]+) 0.05 4 0.02 (m. 2H). 0.00 4
3382 2937
calcd for
489 1771’ 1733’ 6.54 (m. 1H), 5.89 (dq,J=
16777 15727 C31H3TN208, 98, 6.2 HZ, 1H). 490((1, J:
0 5* [452’ 505.2544. found. 9.8 Hz. 1H). 4.58 4 4.48 (m.
1 505.2541 1H). 3.90 (s. 3H). 3.82 (s.
3H). 3.73 (s, 3H). 2.38 (s.
3H). 2.27 (s. 3H). 2.25 (s.
3H). 1.21 (d. J: 0.2 Hz.
3H). 0.95 (d. J = 7.2 Hz.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS N1VJR
No. (cm ) (1H7 13c:1 19F)
1H NMR (500 MHz, CDC13)
6 8.45 (s, 1H), 8.32 (61,7:
.4 Hz, 1H), 7.22 (d, J: 2.1
Hz, 1H), 7.03 (d, .1: 2.2 Hz,
1H), 6.98 (d, .1: 5.5 Hz,
1H), 6.93 (ddd, .1: 8.3, 2.3,
HRMS-ESI (m z)
0.8 Hz, 1H), 6.89 (ddd,J=
(Thin ?lm) ([M+H]+)
8.2, 2.2, 0.8 Hz, 1H), 6.73 (d,
3383, 2937,
calcd for .1: 8.3 Hz, 1H), 6.67 (d, .1:
490 2836, 1772,
C31H3’N208; 8.2 Hz, 1H), 5.85 (dq, J:
1735, 1678,
565.2544; found, 10.0, 6.2 Hz, 1H), 4.95 (d, J
1502, 1453
565.2538 : 10.0 Hz, 1H), 4.58 4 4.46
(m, 1H), 3.90 (s, 3H), 3.82
(s, 3H), 3.72 (s, 3H), 2.38 (s,
3H), 2.25 (s, 3H), 2.21 (s,
3H), 1.22 (d, J: 6.1 Hz,
3H), 0.95 (d, J: 7.1 Hz,
1H NMR (500 MHz, CDC13)
for both isomers ofa 1:1
mixture of reomers d
8.40 (s, 1H), 8.38 (s, 1H),
8.32 (d, J: 5.0 Hz, 1H), 8.31
(d, J: 5.3 Hz, 1H), 7.21 4
HRMS-ESI (m z) 7.13 (m, 2H), 7.03 — 6.83 (m,
(Thin ?lm)
([M+H]+) 12H), 5.76 — 5.63 (m, 2H),
3382, 2985,
.04 (d, .1: 11.9 Hz, 1H),
2941, 2840, calcd for
491 5.02 (d,.]: 11.2 Hz, 1H),
1771, 1736, C29H31F2N2085
4.63 — 4.47 (m, 2H), 3.93 (d,
1677, 1578, 573 .2043; found,
.1: 2.0 Hz, 3H), 3.92 (s, 3H),
1508, 1479 573.2042
3.914 3.89 (m, 6H), 3.80 (d,
J: 1.7 Hz, 3H), 3.76 (d,J=
1.6 Hz, 3H), 2.39 (s, 3H),
2.38 (s, 3H), 1.31 (d, .1: 7.2
Hz, 3H), 1.29 — 1.22 (m,
6H), 1.03 (d, J: 7.2 Hz,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C. 191:)
1H NMR (500 MHz. CDC13)
for the major isomer ofa 2:1
mixture ofdiastereomers d
8.44 (s. 1H), 8.32 (d, J: 5.5
Hz, 1H), 7.18 (dd, .1: 9.7.
HRMS-ESI (m z) 3.0 Hz. 1H), 6.99 (d. .1: 55
(Thin ?lm) ([M+H]+) Hz, 1H). 6.96 (dd, J = 9.5.
3383. 2941, 3.0Hz,1H),6.87—6.79(m,
calcd for
492 2839. 1770. 2H). 6.76 (dd, .1: 9.0. 4.6
CnH~ RN70
1736. 1677, 5732645 £61156 Hz, 1H). 6.72 (d, J = 4.6 Hz.
1592. 1495 573 23045 ’ 1H). 5.87 (dq, J: 9.6, 6.2
Hz. 1H). 4.88 (d. .1: 9.6 Hz.
1H). 4.60 4 4.53 (m, 1H),
3.90 (s. 3H), 3.83 (s, 3H).
3.74 (s, 3H). 2.38 (s. 3H).
1.23 (d. J: 6.2 Hz. 3H), 1.02
(d. J = 7.2 Hz. 3H).
[Annotation] Mel.Chan
None set by an
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd.
MASS N1V1R
No1 (1H7 13c:1 19F)
1H NMR (500 MHz, CDC13)
for 1:1 mixture of
diastereomers 8 8.26 (t, J :
.1 Hz, 4H), 7.07 (ddd, J:
13.9, 79, 111 Hz, 2H), 7.00 —
6.89 (m, 6H), 6.85 (td, .1:
8.8, 8.0, 113 Hz, 2H), 6.78 —
6172(m, 4H), 5.75 — 5,71 (m,
4H), 5.71 2 5.62 (m, 2H),
.12 (dd, J: 13.7, 98 Hz,
2H), 4.63 — 4.47 (m, 2H),
3.91 (s, 3H), 3.90 (s, 3H),
3.89 (s, 3H), 3.86 (s, 3H),
3.84 (s, 3H), 3.83 (s, 3H),
3.81 (s, 3H), 3.80 (s, 3H),
3.74 (s, 3H), 3.71 (s, 3H),
2.06 (s, 6H), 1.32 (d, J: 7.1
112,311), 1.26 (d, .1 : 6.0 Hz,
HRMS-ESI (m 2)
3H), 1.24 (d, J: 6.2 Hz,
([M+H1+)
3H), 1.00 (d, J: 7.2 Hz,
calcd for 3H).
C32H39N2011,
48, found, 13C NMR (126 MHz,
627.2546 CDC13) for 1:1 mixture of
diastereomers 8 172.36,
171.98, 170.28, 162.82,
162.78, 160.26, 16023,
152.82, 152.78, 152.71,
147.42, 147.31, 147.19,
147.11, 145.68, ,
, 142.70, 142.64,
135.14, 134.87, 134.78,
134.61, 123.66, 123.62,
121.05, 120.97, 120.46,
120.33, 110.74, 110.61,
110.55, 109.44, 99.98, 89.63,
89.59, 73181, 7375, 60.40,
60.36, 60.31, 60.25, 56.17,
56.16, 55164, 55.59, 48.18,
48.12, 4196, 41.83, 29.28,
.88, 1886,1871, 18.41,
17.91.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. n .
:\§» \\\\\ ‘\‘\1 MP
MASS NMR
No, \'\'\x ‘ ~‘ (‘0 (1H7 13c:1 19F)
1H NMR (500 MHz, CDC13)
for 1:1 mixture of
diastereomers 8 8.40 4 8,28
(m, 2H), 8.26 (dd, J: 5.3,
3.7 Hz, 2H), 7.07 (ddd, J:
13.1, 8.0, 1.2 Hz, 2H), 7.03 2
6.89 (m, 6H), 6.88 — 6.80 (m,
2H), 6.75 (td, J= 56,28
Hz, 4H), 5.81 4 5.72 (m,
4H), 5.72 — 5.62 (m, 2H),
.12 (dd, J: 13.4, 9.8 Hz,
2H), 4.54 (dp, .1: 17.6, 7.2
Hz, 2H), 3.89 (s, 3H), 3.89
(s, 3H), 3.88 (s, 3H), 3.86 (s,
3H), 3.84 (s, 3H), 3.83 (s,
3H), 3.81 (s, 3H), 3.80 (s,
3H), 3.74 (s, 3H), 3.71 (s,
3H), 2.54 (pd, .1: 7.0, 4.2
Hz, 2H), 1.32 (d, J: 7.1 Hz,
3H), 1.26 (d, J: 6.1 Hz,
SI (m2)
3H), 1.24 (d, J = 6.2 Hz,
([M+H]+)
3H), 1.14 (d, .1: 3.1 Hz,
calcd for 6H),1.13(d,J= 3,1Hz,
C34H43N2O11, 6H), 1.00 (d, J: 7.2 Hz,
655.2861; found, 3H).
655.2858
13C NMR (126 MHz,
CDC13) for 1 :1 mixture of
diastereomers 6 176.26,
176.24, 172.37, ,
, 162.73, 160.25,
160.21, , 152.78,
152.70, 147.42, 147.32,
147.19, 147.11, 145.53,
144.22, 144.16, 142.27,
135.14, 134.88, 134.79,
13462, 123.66, 123.62,
121.06, 120.97, 120.47,
120.33,110.76,110.74,
110.61,110.55,109,39,
99.98, 90.02, 89.95, 73.79,
73.73, 6040, 60.36, 60.31,
60.26, 56.12, 56.10, 55.64,
55.59, 48.18, 48.12, 41.96,
4182,3387, 3385,1885,
18.68,18.41,17,91.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by an
Cmpd. n .
:\§» \\\\\ ‘\‘\1 MP
MASS N1VJR
No, \'\'\x ‘ ~‘ (‘0 (1H, 13c:1 19F)
1H NMR (500 MHz, CDC13)
for 1:1 mixture of
diastereomers 8 8.45 (s, 2H),
8.32 (d, J: 3.9 Hz, 1H), 8.31
(d, J = 3.9 Hz, 1H), 7.07
(ddd, J: 12.2, 8.0, 1.3 Hz,
2H), 7.01 — 6.89 (m, 6H),
6.89 — 6.79 (m, 2H), 6.75 (td,
J: 6,8, 1.5 Hz, 4H), 5.73 2
.60 (m, 2H), 5.12 (d, J:
.1 Hz, 1H), 5.10 (d,J= 9.5
Hz, 1H), 4.61 4 4.52 (m,
1H), 4.52 4 4.44 (m, 1H),
3.91 (s, 3H), 3.90 (s, 3H),
3.89 (s, 3H), 3.86 (s, 3H),
3.83 (s, 3H), 3.83 (s, 3H),
3.81 (s, 3H), 3.80 (s, 3H),
HRMS-ESI (m z) 3.73 (s, 3H), 3.72 (s, 3H),
([M+H]+) 2.39 (s, 3H), 2.38 (s, 3H),
1.30 (d, J: 7.1 Hz, 3H), 1.27
calcd for
495 — 1.22 (m, 6H), 0.98 (d, J:
C31H37N20m,
7.1 Hz, 3H).
597.2443; found,
597.2434
13C NMR (126 MHz,
CDC13) for 1:1 mixture of
diastereomers 6 172.26,
,168.91,162.22,
162.18, 159.42, ,
152.82, 152.77, 15270,
147.40, 147.32, 147.18,
147.11, 146.63, 141.62,
137.45,137,41,135.11,
134.85, 134.76, 134.60,
123.66, 123.64, ,
120.97, 120.48, 120.33,
110.74,110.61,110.55,
109.65, 7383, 73.78, 60.40,
60.38, 60.31, 60.28, 56.28,
56.26, 55165, 55.63, 55.58,
48.01, 4791,4181, 20.76,
18.84, 18.68, 18.48, 18.07.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. m .
:\§» \\\\ \\ ‘\‘
\1 MP
MASS NMR
Nu \'\'\x ‘ ~‘ (‘0 (1H7 13c:1 19F)
1H NMR (500 MHz, CDC13)
for 1:1 mixture of
diastereomers 8 8.43 (s, 2H),
8.32 (d, J: 4.4 Hz, 1H), 8.31
(d, J: 44 Hz, 1H), 7.39 —
7.30 (m, 2H), 7.13 (t,./: 9.0
Hz, 2H), 7.05 — 6.86 (m,
10H), 5.74 — 5.58 (m, 2H),
.09 (d, .1: 9.7 Hz, 1H), 5.06
(d, J: 9.1 Hz, 1H), 4,53 (dq,
J: 15.5, 75 Hz, 2H), 3.91
(s, 3H), 3.90 (s, 3H), 3.83 (s,
3H), 3.79 (s, 3H), 370 (s,
3H), 3.68 (s, 3H), 2139(s,
3H), 2.38 (s, 3H), 2.30 (s,
HRMS-ESI(/1Iz) 3H), 2.29 (s, 3H), 2.25 (s,
([M+H]+) 6H), 1.30 — 1.23 (m, 9H),
0.92 (d, J: 7.2 Hz, 3H).
calcd for
C31H3’N208; 13C NMR (126 MHz,
565.2544, found,
CDC13) for 1:1 mixture of
565.2538
diastereomers 8 172.25,
171.70, , 162.23,
162.17, 159.44, 15940,
156.93, 156.89, 156.82,
156.75, 146.64, 146.57,
141.65, 141.59, 13742,
134.11, , 133.86,
,131.2O,131114,
131.04, 130.95, 130.03,
129.76, 129.70, 126.87,
126.70, 126.65, ,
123.81, 109.65, 74.38, 74.32,
60.31, 6023, 60.20, 56.29,
56.27, 47.98, 47.84, 41.65,
.75,19.06,18.90,18.41,
18.00, 16.68, 1647.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd.
MASS NMR
No. (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
for 1:] mixture of
diastereomers 8 8.50 4 8,23
(m, 4H), 7.13 — 6.92 (m,
8H), 6.86 (t, J: 7.1 Hz, 2H),
6.73 , 6.63 (m, 4H), 5.77 ,
.58 (m, 2H), 4.61 (t, J: 9.4
Hz, 2H), 4.49 (dp, J: 26.5,
7.1 Hz, 2H), 3.90 (s, 3H),
3.89 (s, 3H), 3.79 (s, 3H),
3.78 (s, 3H), 3.76 (s, 3H),
3.75 (s, 3H), 2.38 (d, J: 0.9
Hz, 6H), 228 (s, 3H), 2.26
HRMS-ESI (m/Z) (s, 3H), 2.20 (s, 3H), 2.18 (s,
([M+H]+) 3H), 1.27 (dt, .1: 6.4, 3.2
Hz, 9H), 0.96 (d, J: 7.1 Hz,
calcd for
497 3H).
C31H37N208,
565.2544; found, [73C NMR (101 MHz,
CDC13) for 1:1 e of
diastereomers 8 172.28,
171.77, 168.85, 162.24,
159.41, 157.72, 157.55,
146.61, 141.63, ,
140.51, 140.12, 137.47,
126.12, 126.08, 125.91,
125.42, 120.51, 120.39,
119.92, 119.76, 109.64,
108.32, 7477, 74.71, 56.26,
55.45, 53.40, 48.08, 47.90,
47.55,20.72,18.81, 18.67,
18,29,17.98,11.80,11,73,
11.43.
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.35 (d, .1: 5.5 Hz, 1H),
8.30 (d, J: 5.4 Hz, 1H), 7.07
(ddd, J: 8.2, 5.7, 2.2 Hz,
1H), 7.00 (d, .1: 5.5 Hz,
1H), 6.86 4 6.72 (m, 3H),
.70 — 5.62 (m, 1H), 4.85 (d,
J: 9.4 Hz, 1H), 4.62 — 4.54
(Thin ?lm) (m, 1H), 3.97 (d, .1: 2.3 Hz,
3384, 2942, HRMS-ESI (mz) 3H), 3.91 (s, 3H), 3.83 (d, J
1771, 1737, ([M+H]+) = 2.0 Hz, 3H), 2.38 (s, 3H),
1677,1501, 1.23 (d,.]:6.1Hz,3H),1.11
ca Cldfor
498 1475, 1430, (d, J: 7.2 Hz, 3H).
'3 C29H29F4N2087
1308’ 1200’
609 1855 found 1~
100, 6091851 ° JCNMR(126MHZ,
1057, 950, ' ‘ CDC13) 8 172.04, 168.90,
908, 731 162.27, 159.48, ,
147.34 4 146.78 (111), 146.60,
143.34, 141.37, 137.50,
129.96 — 129.37 (111), 123.61
— 122.42 (111), 110.81 (d,J=
13.5 Hz), 110.68 (d, .1: 13.2
Hz), 109.78, 72.31, 61.44—
60.78(m), 56.31, 4789,
4240,2074, 18.77, 18.11.
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (H, 13C, 19F)
1H NMR (400 MHz, CDC13)
8.43 (s, 1H), 832 (61,7:
.4 Hz, 11117117 6.83 (m,
7H), 5.66 (dq, J: 10.0, 6.1
Hz, 1H), 4.57 — 4.48 (m,
1H), 4.45 (d, .1: 10.0 Hz,
1H), 3.90 (s, 3H), 2.38 (s,
. 3H), 2.35 (s, 3H), 2.29 (3,
gm min) 3H), 2.27 (s, 3H), 2.25 (s,
1771, 1734, ([M+H]+) 3H)” 0 94 (d’ J: 7 2 Hz’ 1 ' , ‘ ,
6:: 1677, 1504,
calcd for 3H).,
490 5
g, 1451, 1310,
C31H3'N206’
‘ 1198 1175 «
1147’ 104,1 533.2646; found, 13C NMR (126 MHz,
9081806” 1 CDC13)6172.41, 168.91,
7130 1 162.25, 159.41, 146.64,
141.58, 139.12, 138.59,
137.44, 135.40, ,
133.59, 133.35, 130.56,
130.27, 128.60, 127.91,
127.20, 126.91, 109.68,
74.87, 56.27, 47.90, 47.34,
21.28, 21.22, 20.75, 19.79,
19.73, 18.86, 17.98.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No, (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.42 (s, 1H), 8.31 (d,./:
.5 Hz, 1H), 7.18 (d, J: 7.9
Hz, 1H), 7.12 (d, J: 8.6 Hz,
1H), 6.98 (d, J: 5.5 Hz,
1H), 6.96 4 6.85 (m, 4H),
.66 (dq, J: 9.9, 6.2 Hz,
1H), 4.57 — 4.48 (m, 1H),
. - 4.43 (d, .1: 10.0 Hz, 1H),
(Thm 111m) 3.90 (s, 3H), 2.38 (s, 3H),
3384, 2938, SI (m/Z)
2 34 (S 3H) 2 30 (S 3H)
1771* 1735’ ([NHHD 2,25 (s: 3H): 2,21 (s: 3H):
calcd for 1.28 (d, J: 6.1 Hz, 3H), 0.96
1 1:; i283
? 7 C31H3‘N206, (d, J: 7.1 HZ, 3H).
1198, 1174,
533.2646; found,,,
1 100 1043 13
9083804 ’ 533.2642 'CNMR(126 MHZ,
7’3 0 ’ CDC13) 5 172.30, 168.92,
162.24, 159.41, 146.64,
141.59, 137.43, 136.50,
136.40, 136.19, ,
135.84, 135.52, 131.49,
131.15, , 127.14,
126.81, 126.59, 109.67,
74.83, 5627, 47.89, 46.82,
.84, 20.81, 20.76, 20.13,
.07, 18.92, 1803.
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.43 (d, .1: 7.9 Hz, 1H),
8.32 (d, J: 5.4 Hz, 1H), 7.13
— 6.98 (m, 4H), 6.91 (dd,J=
.3, 2.8 Hz, 1H), 6.81 (dtd,
.1: 12.5, 8.2, 2.7 Hz, 2H),
.57 (dq, J: 9.6, 6.1 Hz,
1H), 4.61 — 4.51 (m, 1H),
4.46 (d, .1: 9.6 Hz, 1H), 3.90
(s, 3H), 2.38 (s, 3H), 2.34 (s,
3H), 2.29 (s, 3H), 1.32 (d, J
(Thin ?lm) : 6.2 Hz, 3H), 1.02 (d, J:
3379, 2983, HRMS-ESI(I112) 7.2 Hz, 3H).
1770, 1738, ([M+H]+)
1677, 1496, 13C NMR (126 MHz,
calcd for
501 1453, 1310, CDC13) 5 172.15, 168.90,
C H“ RN06
1199,1176, 54i92134115ff0unéi 162.31, 161.35 (d, J: 243.7
1148, 1043, 541 21146 3 Hz), , 146.68,
909, 808, ‘ ' 141.44, 140.63 (d, J : 6,5
729 Hz), 140.14 (d, J: 6.7 Hz),
137.47, 132.40 (d, 1:31
Hz), 132.06 (d, .1: 2.0 Hz),
132.01 (d,J= 3.1 Hz),
131.69 (d, J: 7.8 Hz),
114.83 (d, .1: 22.2 Hz),
114.37 (61.1: 22.3 Hz),
113.65 (d,J= 20.8 Hz),
11337 (d, J: 20.6 Hz),
109.75, 74.02, 56.28,
47.77, 47.72, 20.75, 19.42,
19.35, 18.83, 18.00.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.42 (d, .1: 7.6 Hz, 1H),
8.32 (d, J: 5.4 Hz, 1H), 7.01
— 6.97 (m, 1H), 6.96 — 6.91
(m, 2H), 6,88 (d, J: 9.3 Hz,
1H), 6.86 4 6.81 (m, 1H),
6.70 (dt, J: 9.0, 3.5 Hz,
1H), 6.65 (dt, J: 9.0, 3.5
Hz, 1H), 5.83 (dq, .1: 12.0,
6.1 Hz, 1H), 4.69 (d, J: 10.3
Hz, 1H), 4.57 (p, J: 7.3 Hz,
1H), 3.90 (s, 3H), 3.74 (3,
(Thin ?lm) HRMS-ESI(I1IZ) 6H), 2.38 (s, 3H), 1.30 (d, J
3378, 2940, ([M+H]+) = 6.2 Hz, 3H), 1.02 (d, J:
1770, 1738, 7.1 Hz, 3H).
6616d for
502 1677, 1498,
C29H~1F7N708 11
1207, 1176, "C NMR (126 MHz,
573 2074331611118
1151,1037, #321047 ’ CDC13)6172.11, ,
816, 730 ‘ ' , 159.42, 155.73 (01, J
= 1.8 Hz), 155.57 (d,J= 2.0
Hz), 15519 (d, J: 238.6
Hz), 154.96 (d,.1:238.7
Hz), 146.63, 141.51,
137.44, 127.90 (d, J: 15.8
Hz), 12766 (d, .1: 16.2 Hz),
116.23 (61,1: 24.8 Hz),
115.96 (d,J=24.9 Hz),
115.16, , 113.214
112.82 (m), 109.69, 72.01,
56.28, 55.71, 47.85, 43.39,
.75, 18.96, 18.05.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.42 (s, 1H), 8.32 (d,./:
.4 Hz, 1H), 7,29 (1,,/: 8.7
Hz, 1H), 7.16 (t, J: 8.5 Hz,
1H), 6.99 (d, J: 5.5 Hz,
1H), 6.65 4 6.55 (m, 3H),
6.51 (dd, J: 12.0, 2.6 Hz,
1H), 5.78 (dq, J: 12.1, 6.2
Hz, 1H), 4.66 4 4.52 (m,
2H), 3.90 (s, 3H), 3.75 (s,
. 3H), 3.72 (s, 3H), 2.38 (5,
$719“ $218) 3H), 1,27 (d, .1: 6.2 Hz,
1770’ 17‘36’ HRMS-ESI(I112) 3H), 1.06 (d, J: 7.2 Hz,
’ 4’ ([M+H]+) 3H).
1676,1623,
1585, 1:06, calcd for
503 ”C NMR (126 MHZ,
1444’ 1310’ C29H31F2N208’
CDC1~) 5 172 11‘ 168 91
1195, 1175, 573.2043, found, 1 ~ ,
162.24, 161.24 ((11.1,24517_
1154,1031,, 44,
HZ) 16101(d J:2459
907, 832, , - ,_ »
Hz), 159.72 (d, J— 11.2 Hz),
803, 729
15946 (d, J: 11.3 Hz),
159.44, 146.60, 141.51,
137.44, 129.90 (d,J=5.4
Hz), 12934 (d, J = 5.6 Hz),
11960 (d, .1: 14.6 Hz),
119.45 (d,J: 15.0 Hz),
110.13(d,J=3.0Hz),
109.85 7109.61 (m), 101.99
7 101.44 (m), 72.26, 56.28,
55.50, 55.46, 47.88, 41.64,
.75, 18.93, 18.13.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.40 (s, 1H), 8.3] (d,./:
.4 Hz, 1H), 7.54 (d, J: 8.0
Hz, 1H), 7.30 (d, J: 7.8 Hz,
1H), 7.12 (d, J: 8.0 Hz,
2H), 7.04 4 6.97 (m, 3H),
6.01 — 5.91 (m, 1H), 4.99 (d,
(Thin ?lm) £1191??? 33325361?) 348496
3381, 2942, HRMS—ESI (m z) ;H ; 81
(5’ 3 )1 3‘ (S “7H) 238 (S'3
1772, 1728, ([M+H]+) ’ 3_ * 1
3H), 1.24 (d, J— 6.2 Hz,
1679 1508
‘ ’ calcd for 3H), 0,98 (d, .1: 7.2 Hz,
504 1456, 1417, ,
,, C31H31F6N203, 3H).
1327,1242,
673.1979; found,
1172 112] 13
10331904” 673.1985 ‘CNMR(126MHZ,
739 ’ CDC13) 5 , 162.27,
159.47, 157.54, 157.39,
146.61, 141.44, 137.49,
132.44, 130.44 4 129.46
(m),117.00, 109.74, 107.51
(d, J: 25.6 Hz), 99.99,
71.95, 56.28, 55.73, 55.69,
47.82, 43.70, 20.73, 18.89,
17.97.
1H NMR (400 MHz, CDC13)
8.42 (d, J: 7.9 Hz, 1H),
8.32 (d, .1: 5.5 Hz, 1H), 6.99
(d, J: 5.5 Hz, 1H), 6.66 4
6.53 (m, 4H), 6.45 (ddt, J =
(Thin ?lm) Wiggiff’ Z) 14.8, 10.5, 2.3 Hz, 2H), 5.67
3375, 2939, (dq, J: 99,61 Hz, 1H),
1770, 1677, calcd for 4.62 — 4.49 (m, 1H), 3.94 (d,
0 5
1592, 1509, C26H31F2N2Og, .1: 9.9 Hz, 1H), 3,90 (s, 3H),
1195, 1136, 573.2043, found, 3.76 (s, 3H), 3.75 (s, 3H),
1059, 731 34 2.38 (s, 3H), 1.25 (d, J: 7.6
Hz, 3H), 1.02 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
53—11067, -11 1.17.
ation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.42 (d, .1: 7.7 Hz, 1H),
8.32 (d, J: 5.4 Hz, 1H), 6.98
(d, J: 5.5 Hz, 1H), 6.45 (dd,
.1: 6.5, 2.3 Hz, 4H), 6.28
(dt, .1: 17.4, 2.3 Hz, 2H),
.74 (dq,J= 10.3, 6.1 Hz,
1H), 4.59 — 4.48 (m, 1H),
(Thin ?lm) $111353??? Z) 3.93 4 3.86 (m, 4H), 3.76 (s,
3375, 2938, 6H), 3.74 (s, 6H), 2.38 (s,
1770, 1677, calcd for 3H), 1.28 — 1.22 (m, 3H),
321593, 1203, C3|H37N20|(), 0.97 (d, J: 7.2 HZ, 3H).
: 1152, 1064, 597.2443, found,
731 597.2442 13C NMR (101 MHz,
CDC13) 6 172.26, 168.86,
162.29, 160.95, 160.78,
159.43, 146.64, 143.47,
143.25, 141.64, 137.47,
109.69, 106.48, 106.26,
9854,9844, 72.91, 58.21,
56.26, 55.30, 55.28, 47.92,
.73, 19.23, 18.01.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
ed set by Mel.Chan
Cmpd. m .
:\8 \\\\ \\ ‘\‘
\1 MP
MASS N1VJR
Nu \'\'\
\5‘ (‘0 (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.42 (d, .1: 7.9 Hz, 1H),
8.32 (d, J: 5.4 Hz, 1H), 6.98
(d, J: 5.5 Hz, 1H), 6.69 (d,
.1: 1.5 Hz, 2H), 6,64 (dt, .7:
4.2, 1.9 Hz, 2H), 6.54 (t, .1:
1.9 Hz, 1H), 6.49 (t, J: 1.9
Hz, 1H), 5.73 (dq, J: 10.3,
6.1 Hz, 1H), 4.59 4 4.47 (m,
1H), 3.89 (s, 4H), 3.75 (s,
SI (mt) 3H), 3.73 (s, 3H), 2.38 (s,
(Thin ?lm)
([M+H]+) 3H), 2.28 (3,311), 2.25 (s,
3384, 2939,
3H), 1.23 (d, J: 6.1 Hz,
1771, 1677, calcd for
507 3H), 0.93 (d, J: 7.1 Hz,
1593, 1508, C31H37N208,
l 172, 1 152, 565.2544; found,
1066, 732 565.2540
13CN1\4R(1011V1Hz,
CDC13) 5 172.30, 168.86,
162.27, 159.77, 159.64,
159.43, 146.64, 142.75,
142.51, 141.67, 139.73,
139.31, 137.46, 121.35,
121.29, 112.68, 111.36,
110.95, 109.68, 73.23, 57.88,
56.26, 55.15, 55.13, 47.91,
29.30, 21.67, 21.60, 20.73,
19.27, 17.96.
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd.
MASS N1VJR
No1 (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.40 (d, .1: 7.9 Hz, 1H),
8.31 (d, J: 5.4 Hz, 111), 7,06
— 6.94 (m, 3H), 6.80 (ddd, J
= 7.7,61, 1.7 Hz, 2H), 6.73
(dd, .1: 14.2, 1.6 Hz, 2H),
.79 (dq,J= 10.1, 6.1 Hz,
1H), 4.60 — 4.47 (m, 1H),
3.96 (d, .1: 10.1 Hz, 1H),
3.89 (s, 3H), 3.79 (s, 3H),
HRMS-ESI (m/Z)
3.79 (s, 3H), 2.38 (s, 3H),
(Thin ?lm) ([M+H]+) 2. 14 (s, 3H), 2.11 (s, 3H),
3376,2939,
calcd for 1.24 (d, J : 6.4 Hz, 311), 0.93
508 1771, 1678,
C31H3‘N208, (d, J: 7.2 Hz, 3H).
1508, 1201,
565.2544; found,
1040, 734
565.2538 13C NMR (101 MHZ,
CDC13)6172.31, 168.86,
162.28, 159.44, 157.84,
157.65, 146.62, 141.65,
140.39, 140.28, 137.48,
130.75, 130.48, 125.19,
124.79, 119.76, 119.68,
109.94, 109.85, 109.69,
73.32, 57.89, 56.26, 55.29,
47.93, 29.30, 20.73, 19.30,
17.97,15.80,15175.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. n .
:\§» \\\\\ ‘\‘\1 MP
MASS N1VJR
No. \'\'\
\5‘ (‘0 (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.40 (d, .1: 7.9 Hz, 1H),
8.32 (d, J: 5.4 Hz, 1H), 7.04
— 6.91 (m, 5H), 6.86 (dt, J=
SI (m z) 7 Hz, 2H), 5.63 (dq, ,1
(Thin ?lm)
([M+H]+) : 94,61 Hz, 1H), 4.64 4
3373,2939,
4.51 (m, 1H), 3.92 (d, J: 9.5
1770, 1676, calcd for
509 Hz, 1H), 3.90 (s, 3H), 3.84
1513, 1276, C29H31F2N2O8,
(s, 3H), 3.82 (s, 3H), 2.38 (s,
1201, 1026, 573.2043, found,
3H), 1.22 (d, J: 6.2 Hz,
731 573 .2033
3H), 1.05 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
-13420, —134.64.
1H NMR (400 MHz, CDC13)
68.43 (s, 1H), 831 (d,./:
.5 Hz, 1H), 7.12 4 6.94 (m,
5H), 6.70 (dd, J: 14.1, 8.4
Hz, 2H), 5.69 (dq, J: 9.9,
6.1 Hz, 1H), 4.60 4 4.49 (m,
1H), 3.89 (s, 3H), 3,87 (d, J
= 10.6 Hz, 1H), 3.77 (s, 3H),
3.74 (s, 3H), 2.38 (s, 3H),
HRMS-ESI(I11Z) 2.16 (s, 3H), 2.14 (s, 3H),
(Thin ?lm) +) 1.21 (d, J: 6.1 Hz, 3H), 0.95
3386, 2939,
calcd for (d, .1: 7.1 Hz, 3H).
510 1771, 1677,
N208,
1504, 1201,
565.2544, found, 13CN1\4R(1011V1Hz,
1176, 732
565.2526 CDC13) 6 172.30, 168.86,
162.26, 159.43, 156.52,
156.35, 146.63, 141.69,
137.46, 133.70, 133.57,
130.50, 130.37, 126.79,
126.37, 126.10, 125.87,
110.05, 109.92, 109.67,
73.70, 56.26, 56.23, 55.31,
55.29, 47.94, 20.73, 19.29,
18.08, 16.32, 16.25.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. m .
:\§» \\\\\ ‘\‘\1 MP
MASS N1VJR
Nu \'\'\
\a‘ (‘0 (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
6 8.50 4 8.35 (m, 1H), 8.31
(d, J: 5.4 Hz, 1H), 7.07 (d,
J: 3.0 Hz, 1H), 6.97 (d,J=
.5 Hz, 1H), 6.87 (d, .1: 3.0
Hz, 1H), 6.80 4 6.60 (m,
4H), 5.91 (dq, J: 9.9, 6.1
Hz. 1H), 4.93 (d, J: 10.0
Hz, 1H), 4.62 4 4.45 (m,
1H), 3.89 (s, 3H), 3.81 (s,
HRMS-ESI (7112) 3H), 3.74 (s, 3H), 3.71 (s,
(Thin ?lm)
([M+H]+) 3H), 3.70 (s, 3H), 2.38 (s,
3387, 2940,
3H), 1.23 (d, J: 6.1 Hz,
1771, 1678, calcd for
511 3H), 0.97 (d, J: 7.1Hz,
1499, 1223, C31H37N2010,
1046, 808, 597.2443; found,
732 597.2410 13CN1\4R(1011V1Hz,
CDC13)8 172.29, ,
162.24, 159.40, 153.47,
153.45,151.89,151.77,
146.63, 141.73, 137.43,
130.69, 116.44, 115.43,
112.14,112.11,111.84,
111.55, 109.63, 73.04, 56.33,
56.29, 56.25, 55.68, 55.59,
47.96, 930, 2073,
1891,1813
[Annotation] Mel.Chan
None set by Mel.Chan
ation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.43 (d, .1: 8.0 Hz, 1H),
8.31 (d, J: 5.4 Hz, 1H), 7,05
(d, J: 8.3 Hz, 1H), 7.01 —
6.94 (m, 2H), 6.90 (d, .]= 2.7
Hz, 1H), 6.82 (d, .1 : 2.7 Hz,
1H), 6.63 (ddd, J: 18.7, 8.4,
2.7 Hz, 2H), 5.65 (dq, J:
.1, 6.1 Hz, 1H), 4.59 4
4.49 (m, 1H), 4.45 (d, J:
.0 Hz, 1H), 3.89 (s, 3H),
(Thin ?lm) HRxais?ff Z) 3.73 (s, 3H), 3.73 (s, 3H),
3381, 2939, 2.38 (s, 3H), 2.32 (s, 3H),
1771, 1677, calcd for 2.27 (s, 3H), 1.31 (d, J: 6.1
1502, 1200, CngyNZOg, Hz, 3H), 0.97 (d, .1: 7.1 Hz,
in: 1175, 1043, 565.2544; found, 3H).
731 565.2543
(101 MHz,
CDC13)6 172.26, 168.85,
162.28, 159.43, 157.92,
157.89, 146.64, ,
140.31, 139.86, 137.47,
131.43,131.10,128.88,
128.61, 114.65, 113.69,
111.27,111.11,109.70,
74.59, 56.26, 55.19, 47.90,
47.86, 2930,2073, 19.29,
19.25, 18.90, 17.99.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS N1VJR
No, (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.27 (d, .1: 5.4 Hz, 1H),
8.23 (d, J: 7.8 Hz, 1H), 6.94
(d,J= 5.4 Hz, 1H), 6.60
(dddd, .1: 13.2, 108, 3.9,
(Thin ?lm) HRMS-ESI (m Z) 1.8 Hz, 4H), 6.45 (ddt, .1:
3381, 2940, ([M+H]+) 13.9, 10.5, 2.3 Hz, 2H), 5.76
1740, 1675, — 5.63 (m, 3H), 4.57 (p,J=
calcd for
1592, 1505, 7.3 Hz, 1H), 3.95 (d, .1: 10.0
C30H33FZNZO97
1200, 1134, Hz, 1H), 3.90 (s, 3H), 3.77
1045,829, 603.2149, found,
(s, 3H), 3.75 (s, 3H), 2.06 (s,
603.2137
730 3H), 1.26 (d, .1: 6.1 Hz,
3H), 1.04 (d, J: 7.2 Hz,
"’F NMR (376 MHz, CDC13)
-110.67, —111.20.
'H NMR (400 MHz, CDCH)
8 8.26 (d, J: 5.4 Hz, 1H),
8,23 (d, J: 7.8 Hz, 1H), 6.93
(d, .1: 5.4 Hz, 1H), 6.46 (dd,
J: 7.4, 22 Hz, 4H), 6.28
(dt, J = 16.6, 2.2 Hz, 2H),
.814 5.68 (m, 3H), 4.55 (p,
J: 7.2 Hz, 1H), 3.96 — 3.86
(Thin ?lm) SI (m/Z)
(m, 4H), 3.76 (s, 6H), 3.74
3382, 2937, ([M+H]+)
(s, 6H), 2.06 (s, 3H), 1.26 (d,
1737, 1675,
calcd for J: 6.2 Hz, 3H), 0.99 (d,J:
514 1593, 1457,
C32H39N2O11, 7.2 Hz, 3H).
1202, 1150,
627.2548; found,
1062, 829,
627.2555 [73C NMR (101 MHz,
CDC13) 5 172.37, 170.22,
162.89, , 160.79,
160.25, 145.70, ,
143.51, 143.26, 142.65,
109.51, 106.49, 106.24,
98.54, 98.43, 89.57, 72.87,
58.24, 56.17, 55.30, 55.28,
48.14, 20.85, 19.25, 17.84.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS N1VJR
No. (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.27 (d, .1: 5.4 Hz, 1H),
8.23 (d, .7: 7.8 Hz, 1H), 6.93
(d, J: 5.4 Hz, 1H), 6.70 (s,
2H), 6.65 (dt, .1: 5.7. 1.9
Hz, 2H), 6.55 (t, .1: 1.7 Hz,
1H), 6.50 (t, J: 1.7 Hz, 1H),
.80 — 5.66 (m, 3H), 4.54 (p,
.1: 7.2 Hz, 1H), 3.93 4 3.87
(m, 4H), 3.75 (d, J: 7.3 Hz,
HRMS-ESI (m/Z)
(Thin ?lm) 6H), 2.29 (s, 3H), 2.25 (s,
([M+H]+)
3382, 2937, 3H), 2.06 (s, 3H), 1.24 (d, .1
1738, 1676, calcd for : 6.1 Hz, 3H), 0.95 (d, J:
1594, 1504, N209, 7.1 Hz, 3H).
1293, 1202, 595.2650; found,
1152 595.2647 l3C 1 MHz,
CDC13) 6 172.41, 170.22,
162.88, 160.25, 159.77,
159.65, 145.70, 143.93,
142.79, 142.70, 142.52,
139.73,139.31,121.35,
121.30,112.69,111.36,
110.92, 109.50, 89.57, 73.19,
57.91, 56.16, 55.15, 55.14,
48.13, 29.30, 21.67, 21.60,
.85, 19.29, 17.79.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
MASS NMR
No, (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.26 (d, .1: 5.4 Hz, 1H),
8.21 (d, J: 7.8 Hz, 1H), 7.05
— 6.96 (m, 2H), 6.93 (d, J:
.4 Hz, 1H), 6.81 (td,J=
7.4, 1.6 Hz, 2H), 6.76 (d, .1:
1.6 Hz, 1H), 6.72 (d, J: 1.6
Hz, 1H), 5.79 (dq, J: 10.1,
6.2 Hz, 1H), 5.72 (d, .1: 1.4
Hz, 2H), 4.55 (p, J = 7.2 Hz,
1H), 3.97 (d, J: 10.2 Hz,
HRMS-ESI (m Z) 1H), 3.90 (s, 3H), 3.80 (s,
(Thin ?lm)
([M+H]+) 3H), 3.79 (s, 3H), 2.14 (s,
3382, 2936,
3H), 2.11 (s, 3H), 2106(s,
1737, 1676, calcd for
516 3H), 1.26(d,.1: 6.2 Hz,
1505, 1202, C32H39N209,
3H), 0.94 (d, J: 7.2 Hz,
1040, 969, 595.2650, found,
730 595.2639
[73C NMR (101 MHz,
6172.43, 170.21,
162.89, , 157.85,
157.65, 145.68, 143.94,
142.67, 140.44, ,
130.75, 130.48, 125.19,
124.78, 119.75, 119.67,
109.94, 109.86, 109.52,
89.56, 73.28, 57.91, 56.17,
55.29, 5528,4816, 20.85,
19.32,17.82,15.80,15.75.
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.27 (d, .1: 5.4 Hz, 1H),
8.23 (d, J: 7.9 Hz, 1H), 7.04
— 6.92 (m, 5H), 6.87 (q, J=
HRMS-ESI(I17Z) 8.7 HZ, 2H), 5.72 (s, 2H),
(Thin ?lm) ([M+H]+) 5.64 (dq, .1: 9.5, 6.2 Hz,
3382,2984, 1H), 4.65 — 4.48 (m, 1H),
calcd for
517 1739, 1675, 3.93 (d, J: 9.7 Hz, 1H), 3.91
CmHvaNyOo
\ 1512, 1275, 603‘ 2129: 1‘6und (s, 3H), 3.84 (s, 3H), 3.83 (s,
1202, 730 603 21137 ’ 3H), 2.06 (s, 3H), 1.24 (d, J
' =61 Hz, 3H), 1.06 (d,J=
7.2 Hz, 3H).
191: NMR (376 MHz, CDC13)
8 -13420, —134.65.
1H NMR (400 MHz, CDC13)
8.27 (s, 1H), 8.23 (d,./:
7.9 Hz, 1H),7.11 4 6.99 (m,
5H), 6.93 (d, J: 5.3 Hz,
1H), 6.71 (dd, J: 12.0, 8.4
Hz, 2H), 5.74 4 5.65 (m,
3H), 4.55 (p, J: 7.2 Hz,
1H), 3.90 (s, 3H), 3.77 (s,
3H), 3.75 (s, 3H), 2.16 (s,
HRMS-ESI (m 2) 3H), 2.14 (s, 3H), 2.06 (3,
(Thin ?lm) ([M+H]+) 3H), 1.23 (d, J: 6.2 Hz,
3382, 2941, 3H), 0.97 (d, .1: 7.2 Hz,
calcd for
518 1737, 1676, 3H).
4 C32H39N209,
‘ 11555; 172353” 50, found,
3’ 3 13C NMR ( 10] MH2’
595.2645
CDC13) 6 , 170.22,
162.87, 160.26, 156.53,
156.36, 145.68, 143.94,
142.72, 133.75, 133.58,
130.48, 130.36, 126.81,
126.38, 126.10, 125.87,
110.06, 109.93, 109.49,
89.58, 73.66, 56.27, 56.16,
55.33, 55.30, 48.16, 20.85,
19.32, 1?.91, 16.33, 16.25.
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. n .
:\1» \\\\\ ‘\‘\1 MP
MASS NMR
No, \'\'\
13‘ (‘0 (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.25 (dd, .1: 6.5, 3.4 Hz,
2H), 7.07 (d, .1: 3.0 Hz,
1H), 6.92 (d, J: 5.4 Hz,
1H), 6.87 ((17: 31 Hz,
1H), 6.77 (d, .1: 8.8 Hz,
1H),6.71(d,J= 8.8 Hz,
1H), 6.66 (ddd, J: 11.1, 8.9,
3.0 Hz, 2H), 5.92 (dq, .1:
9.9, 6.1 Hz, 1H), 5.72 (d,J=
1.7 Hz, 2H), 4.94 (d, J: 10.0
Hz, 1H), 4.56 (p, .1: 7.2 Hz,
HRMS-ESI (/77 Z)
1H), 3.89 (s, 3H), 3.81 (s,
(Thin ?lm) ([M+H1+)
3H), 3.74 (s, 3H), 3.72 (s,
3381, 2939,
calcd for 3H), 3.71 (s, 3H), 2.06 (s,
519 1737, 1676,
C32H39NZOU: 3H), 1.25 (d, J: 6.3 Hz,
1498, 1233,
627.2548; found, 3H), 0.99 (d, J: 7.2 Hz,
1043, 729
627.2541 3H).
13CN1\4R(101 MHz,
CDC13)6 172.39, 170.22,
, 160.23, 153.47,
153.45,151.89,151.78,
145.68, 143.88, 142.78,
130.73, 130.69, 116.45,
115.38,112.14,112.13,
111.83,111.55,109.45,
89.59, 73.02, 56.34, 56.29,
56.15, 55.67, 5559,4817,
43.90,20.86,18.91, 17.97.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No, (0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.26 (d, .1: 5.4 Hz, 1H),
8.23 (d, J: 7.8 Hz, 1H), 7.05
(d, J: 8.5 Hz, 1H), 6.98 (d,
.1: 8.4 Hz, 1H), 6,93 (d, J:
.4 Hz, 1H), 6.90 (d, .1: 2.7
Hz, 1H), 6.82 (d, J = 2.7 Hz,
1H), 6.63 (ddd, J: 18.1, 8.3,
2.7 Hz, 2H), 5.72 (d, .1: 1.6
Hz, 2H), 5.66 (dq, J: 10.0,
6.1 Hz, 1H), 4.56 (p, J: 7.3
. HRMS—ESI (m z) Hz, 1H), 4.46 (61,7: 10.1
?“ min) ([M4H]+) Hz, 1H), 3.90 (s, 3H), 3.73
3382, 2937, 5
,5, (s, 6H), 2.33 (s, 3H), 2.28 (s,
;, 1759, 1677,, calcd for
520 3H), 2.06 (s, 3H), 1.32 (d, .1q q 4
1500, 1455, C32H36N200,
: 6 1 H ,H) 0 99 (d J:
1202, 1042, 595.2650; found, ' 7‘Z’2’H gm ’
730 595.2652 ' '
[73C NMR (101 MHz,
CDC13) 6 , 170.22,
162.89, 160.25, ,
157.89, 145.69, 143.92,
142.66, 140.37, 139.85,
131.44,131.11,128.89,
128.62, 114.67, 113.64,
111.28,111.11, 109.52,
89.57, 74.55, 56.17, 55.19,
48.13, 47.87, 29.30, 20.86,
19.30, 1926,1888, 17.81.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No, (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.39 (d, .1: 7.1 Hz, 1H),
8.31 (d, J: 5.4 Hz, 1H), 7.44
(dd, J: 8.7, 5.0 Hz, 1H),
7.23 (dd, J: 8.7, 5.0 Hz,
1H), 7.1 1 (dd, .1: 9.0, 2.8
Hz, 1H), 7.07 (dd, J: 9.7,
2.8 Hz, 1H), 7.00 (d, J: 5.5
HRMS-ESI (/17 Z) Hz, 1H), 0.90 4 0.87 (m,
(Thin ?lm)
([M+H]+) 2H), 5.00 (dq, J: 815, 0.2
Hz, 1H), 4.09 (d, J: 8.8 Hz,
1769, 1737, calcd for
521 1H), 4.02 (d, .7: 12.4 Hz,
1677, 1496, C31H35F2N208,
1H), 4.00 4 4.53 (m, 1H),
1195, 1174, 602.23 89, found,
4.50 (d, J: 12.0 Hz, 1H),
1095 60223 95
4.44 (d, .1: 12.5 Hz, 1H),
4.40 (d, J: 12.5 Hz, 1H),
3.90 (s, 3H), 3.43 (s, 3H),
3.38 (s, 3H), 2.39 (s, 3H),
1.28 (d, J: 0.2 Hz, 3H), 1.04
(d, J: 7.2 Hz, 3H).
"’1? NMR (370 MHz, CDClg)
—115.57, —115.90.
[Annotation] an
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS N1VJR
No. (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.40 (d, .1: 6.4 Hz, 1H),
8.31 (d, J: 5.4 Hz, 1H), 7.45
(dd, J: 8.7, 5.6 Hz, 1H),
7.21 (dd, J: 8.7, 5.6 Hz,
1H), 7.17 4 7.05 (m, 2H),
7.00 (d, J: 5.5 Hz, 1H), 6.97
FIRMS-13810772) — 6.82 (m, 2H), 5.62 (dq, J:
(Thin ?lm)
+) 8.2, 6.2 Hz, 1H), 4.70 (d, .1:
3385, 2976,
8.7 Hz, 1H), 4.67 (d, J: 12.7
1770, 1738, calcd for
522 Hz, 1H), 4.62 — 4.50 (m,
1678, 1506, C33H39F2N2O8,
2H), 4.48 (d, J: 12.5 Hz,
1200, 1 175, 629.2669; found,
1H), 4.43 (d, J: 12.7 Hz,
1155, 1096 629.2666
1H), 3.90 (s, 3H), 3.62 —
3.45 (m, 4H), 2.39 (s, 3H),
1.30 4 1.25 (m, 6H), 1.23 (t,
J: 7.0 Hz, 3H), 1.05 (d,J=
7.2 Hz, 3H).
19F NMR (376 MHz, CDC13)
415.69, 415.98.
1HNMR (400 MHz, CDC13)
8.41 (d, J: 6.8 Hz, 1H),
8.30 (d, .1: 5.4 Hz, 1H), 7.36
— 7.28 (m, 2H), 7.26 — 7.18
HRMS-ESI (m~"'z) (m, 2H), 7.18 — 7.10 (m, 2H),
([M+H]+) 6.97 (d, .1: 5.5 Hz, 1H), 6.67
_ 6.46 (m, 2H), 5.83 (dq, J:
calcd for
523 9.9, 6.2 Hz, 1H), 4.62 — 4.46
C28H30FN2O7,
(m, 2H), 3.87 (s, 3H), 3.82
525.203 7; found,
(s, 3H), 2.38 (s, 3H), 1.23 (d,
525.2025
J: 6.2 Hz, 3H), 0.91 (d,J=
7.1 Hz, 3H).
19F NMR (376 MHz, CDC13)
—113.24.
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No1 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.40 (d, .1: 7.9 Hz, 1H),
8.30 (d, J: 5.4 Hz, 1H), 7.35
— 7.17 (m, 5H), 7.17 - 7.08
HRMS-ESI (m z) (m, 1H), 6.97 (d, J: 5.5 Hz,
([M+H]+) 1H), 6.93 _ 6.79 (m, 2H),
,,HANK/5.; 5.77 (dq, J: 10.2, 6.1 Hz,
calcd for
524 ;;'41/ 1H), 4.60 — 4.47 (m, 1H),
C28H30FN2O6,
.v2/. 4.28 (d, .1: 10.2 Hz, 1H),
,, 509.2088; found,
3.87 (s, 3H), 2.38 (s, 6H),
509.2083
1.26 (d, J: 6.1 Hz, 3H), 0.93
(d, .1: 7.2 Hz, 3H).
19F NMR (376 MHz, CDC13)
-11666.
1H NMR (400 MHz, CDC13)
8.42 (d, .1: 8.1 Hz, 1H),
8.30 (d, .1: 5.6 Hz, 1H), 7.35
- 7.21 (m, 5H), 7.17 (ddt, J=
65,54, 18 Hz, 1H), 6.98 (d,
HRMS-ESI (/17 Z)
.1: 5.4 Hz, 1H), 6.58 (td, .1:
([M+H]+)
8.3, 2.6 Hz, 1H), 6.51 (dd, J
calcd for = 10.9, 2.5 Hz, 1H), 5.81
CZXH30FNZO77 (dq,.]: 10.1,61 Hz, 1H),
525.203 7; found, 4.63 — 4.43 (m, 2H), 3.87 (s,
525.2035 3H), 3.75 (s, 3H), 2.38 (s,
3H), 2.15 (s, 3H), 0.99 (d, .1
: 7.1 Hz, 3H)
19F NMR (376 MHz, CDClg)
-11359.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP
MASS NMR
No. (‘0 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.47 - 8.36 (m, 1H), 8.31
(d, J: 5.4 Hz, 1H), 7.35 (dd,
J: 8.7, 5.7 Hz, 1H), 7.30 —
7.15 (m, 5H), 6.99 (d, .]= 5.5
HRMS-ESI (m Z) Hz, 1H), 6.85 (1d, .1: 8.4,
([M+H]+) 2.8 Hz, 1H), 6.79 (dd, J:
9.8, 2.8 Hz, 1H), 5.73 (dq, J
calcd for
526 : 10.0, 6.1 Hz, 1H), 4.60 -
C28H30FN2067
4.47 (m, 1H), 4.26 (d, .1:
509.2088; found,
.0 Hz, 1H), 3.89 (s, 3H),
509.2079
2.38 (s, 3H), 2.30 (s, 3H),
123 (d, J: 6.1 Hz, 3H), 0.96
(d, J: 7.1 Hz, 3H).
"’F NMR (376 MHz, CDC13)
lH NMR (400 MHz, CDCH)
8 8.41 (d, J: 5.0 Hz, 1H),
8.30 (d, J: 5.4 Hz, 1H), 7.23
— 7.19 (m, 2H), 7.19 — 7.10
(m, 1H), 7,03 (d, J: 7.9 Hz,
SI (m/Z)
2H), 6.97 (d,.]= 5.5 Hz,
([1V1+H]+)
1H), 6.63 — 6.50 (m, 2H),
calcd for 5.80 (dq,J: 9.6, 6.1 Hz,
C29H32FN2O7, 1H), 4.61 — 4.46 (m, 2H),
539.2193; found, 3.88 (s, 3H), 3.81 (s, 3H),
539.2180 2.38 (s, 3H), 2.25 (s, 3H),
1.22 (d, J = 6.2 Hz, 3H), 0.95
(d, .1: 7.2 Hz, 3H).
19F NMR (3 76 MHz, CDC13)
a —113.44_
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No. (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.40 (d, .1: 8.6 Hz, 1H),
8.31 (d, J: 5.4 Hz, 1H), 7.28
(dd, J: 8.8, 5.9 Hz, 1H),
7.18 - 7.10 (m, 2H), 7.02 (d,
HRMS-ESI (m Z) .1: 79 Hz, 2H), 6.98 (d, .1:
([M+H]+) 5.5 Hz, 1H), 6.92 — 6.78 (m,
2H), 5.74 (dq, J: 10.0, 6.1
calcd for
528 Hz, 1H), 4.62 _ 4.45 (m, 1H),
C29H32FN2067
4.24 (d, J: 10.1 Hz, 1H),
523.2244; found,
3.88 (s, 3H), 2.38 (s, 3H),
2.37 (s, 3H), 2.24 (s, 3H),
1.24 (d, J: 6.1 Hz, 3H), 0.97
(d, J: 7.2 Hz, 3H).
"’F NMR (376 MHz, CDC13)
-116.88.
'H NMR (400 MHz, CDCH)
8 8.41 (d, J: 7.9 Hz, 1H),
8,31 (d, J: 5.4 Hz, 1H), 7.37
—7.23 (m, 1H), 7.20 — 7.12
(m, 2H), 7,06 (d, J: 7.8 Hz,
2H), 6.98 (d,.]= 5.5 Hz,
HRMS-ESI (m z)
1H), 6.57 (td, .1: 8.3, 2.5
([M+H]+)
Hz, 1H), 6,50 (dd, J: 11.0,
calcd for 2.6 Hz, 1H), 5.78 (dq, J=
C29H32FN2O7, 102,61 Hz, 1H), 4.69 — 4.41
539.2193; found, (m, 2H), 3189(5, 3H), 3.76
539.2182 (s, 3H), 2.38 (s, 3H), 2.27 (s,
3H), 1.21 (d, .1: 6,] Hz,
3H), 0.98 (d, .1: 7.1 Hz,
"’1? NMR (376 MHz, CDClg)
-113.82.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS NMR
No. (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.40 (s, 1H), 8.30 (d,./:
.4 Hz, 1H), 7,33 (dd, J:
8.7, 5.8 Hz, 1H), 7.20 — 7.04
(m, 4H), 6.98 (d, J: 5.5 Hz,
1H), 6.84 (td, .1: 8.5, 2.9
HRMS-ESI(I1IZ)
Hz, 1H), 6.77 (dd, J: 9.6,
([M+H]+) 2.4 Hz, 1H), 5.71 (dq,J=
calcd for 10.1, 6.1 Hz, 1H), 4.61 -445
C29H32FN206, (m, 1H), 4.21 (d, J: 10.1
523 .2244; found, Hz, 1H), 3.89 (s, 3H), 2.38
523 .2229 (s, 3H), 2.30 (s, 3H), 2.28 (s,
3H), 1.23 (d, J: 6.0 Hz,
3H), 0.96 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
-11733.
1H NMR (400 MHz, CDC13)
8.40 (d, .1: 6.0 Hz, 1H),
8.30 (d, .1: 5.5 Hz, 1H), 7.35
- 7.22 (m, 2H), 7.13 (dd, J:
8.3, 6.4 Hz, 1H), 6.99 (d,J=
HRMS-ESI (m z)
.5 Hz, 1H), 6.96 - 6.84 (m,
2H), 6.65 - 6.51 (m, 2H),
calcd for 5.79 (dq, J: 9.7, 6.2 Hz,
C28H29F2N207, 1H), 4.64 _ 4.47 (m, 2H),
543.1943; found, 3.88 (s, 3H), 3.81 (3,311),
36 2.38 (s, 3H), 1.23 (d, J: 6.1
Hz, 3H), 0.99 (d, .1: 7.2 Hz,
19F NMR (376 MHz, CDCl;)
4129241648.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by an
Cmpd. 53:; MP IR NMR
3445s
Nb‘ g 6C) (mn4) GH;BC,”F)
?iymy?3(40034Hz,cx)Ch)
J:32Hz1HL
83lmw]:54fk,u?,729
:HMm3?6%@J=
Hmnggonm 55H11HL6WL681mL
QNHHT) 4Hl57IMqJ:lOL64
Hz, 1H), 4.60 — 4.49 (m, 1H),
calcd for
532 y\ 426(d?l=10()Hz,H{)
C28H20F2N2Oo, 4 ’3 ’3 a
x ‘189(S*3FD’2J8(S’3H)
5271993'fbund
5271584 ’ 235(3,3HL J==62
' Hz3HyLmu¢J=12Hz
”FrmuR4376hmHz(j)Ch)
—H6oz—H638
?iymy?3(40034Hz,cx)Ch)
58M(¢J:58HZIHL
8MM¢J:54H11HL7B
-7l8(nL3}D,702-689
HMM$E$OHQ (m ??658a¢J=8425
QNH{H+) HLIPD,652(dd“/:109,
26I{;]}D,576(dq?l=
cam for
533 10.0, 6.2 Hz, 1H), 4.60 — 4.46
C28H20F2NZO77 a ’3 a
yBJWBAmmd OEZHl388§”H1375
(S, 3H), 2.38 (S, 3H), 1.21 (d,
543.1928
J=62HL3HLLW(¢J=
12HL3H)
mFT?y?{(376h{Hz,C?)Ch)
3—H32@_H64L
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
CmNE.d. MP 1R NMR
(0C) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.40 (d, .1: 8.1 Hz, 1H),
8.30 (d, J: 5.4 Hz, 1H), 7.33
(dd, J: 8.6, 5.7 Hz, 1H),
7.23 _ 7.13 (m, 2H), 7.04 _
HRMS-ESI(/11z) 6.92 (m, 3H), 6.86 (td, J:
([M+H]+) 8.5, 2.8 Hz, 1H), 6.80 (dd, J
= 9.7, 2.8 Hz, 1H), 5.69 (dq,
534 .1: 9.9, 6.2 Hz, 1H), 4.63 — C) ‘jg
52281 93317 £61138 4.45 (m, 1H), 4.24 (d, J: 9.8
€27 11985 1 Hz, 1H), 3.89 (s, 3H), 2.38
1 ' (s, 3H), 2.28 (s, 3H), 1.23 (d,
J: 6.1 Hz, 3H), 0.99 (d,J:
7.2 Hz, 3H).
”P NMR (376 MHz, CDC13)
8 —115.54, -116.80.
'H NMR (400 MHz, CDCH)
8.49 — 8.39 (m, 1H), 8.30
(d, J: 5.5 Hz, 1H), 7.19 —
. - HRMS-ESI m z) 7.053H)? 5.78 (dq, J: 10.2,m, 6H 7.01 4 6.92
111161) ([M+H]+() , 6(.1m,
3385,2982,
Hz, 1H), 4.59 — 4.46 (m,
535, 1771,1737,, calcdfor
1H) 396(d 1:102HZ
1679, 1605, C26H33N200, 505.233, 1H)1 3'86 (31m) 2137 (37
1508 found, 505.2333 1 1 1 1 ‘ 1
3H), 2.30 (s, 3H), 2.27 (s,
3H), 1.23 (d, .1: 6.2 Hz,
3H), 0.90 (d, J: 7.2 Hz,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd.
MASS N1VJR
No1 (cm ) (1H7 13c:1 19F)
1H NMR (400 MHz, CDC13)
8.41 (d, .1: 5.6 Hz, 1H),
8.31 (d, J: 5.4 Hz, 1H), 7,23
(dd, J: 8.5, 6.6 Hz, 1H),
7.16 (dd, J: 8.6, 5.9 Hz,
1H), 6.99 (d, .1: 5.5 Hz,
1H), 6.81 (qd,J= 9.1, 8.3,
HRMS-ESI (m/Z)
2.8 Hz, 2H), 6.57 (td, J=
(Thin ?lm) ([M+H]+)
83,25 Hz,
" 1H), 6.51 (dd, .1
',cdyér.’ 3377, 2985,
calcd for = 10.8, 25 Hz, 1H), 5.68
536 av 1771, 1736,
2:,tz, C29H31F2N2O7, (dq,J= 10.0, 6.1 Hz, 1H),
ait. 1677, 1502,
«7 557.2094; found, 4.74 (d, .1: 10.0 Hz, 1H),
557.2082 4.62 — 4.49 (m, 1H), 3.90 (s,
3H), 3.76 (s, 3H), 2.42 (s,
3H), 2.38 (s, 3H), 1.21 (d, .1
: 5.9 Hz, 3H), 1.04 (d,J:
7.2 Hz, 3H).
"’F NMR (376 MHz, CDC13)
—113.52, —117.02.
'H NMR (400 MHz, CDCH)
8.40 (d,J= 6.1 Hz, 1H),
8.31 (d, J: 5.4 Hz, 1H), 7.31
(dd, .1: 8.4, 6.7 Hz, 1H),
HRMS-ESI (m z) 7,23 — 7.14 (m, 1H), 6.99 (d,
(Thin ?lm) ([M+H]+) J: 5.5 Hz, 1H), 6.84—6.68
3376, 2940, (m, 2H), 6.58 (td, .1: 83,25
calcd for
537 1770, 1737, Hz, 1H), 6.52 (dd, J: 10.8,
F3NZO7:
1678, 1601, 2.5 Hz, 1H), 5.86 — 5.73 (m,
561.1843, found,
1502, 1 196 1H), 4.78 (d, .1: 9.9 Hz,
561 . 1836
1H), 4.65 4 4,43 (m, 1H),
3.90 (s, 3H), 3.75 (s, 3H),
2.38 (s, 3H), 1.24 (d, .1: 6.1
Hz, 3H), 1.04 (d, .1 : 7.2 Hz,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.44 4 8.37 (m, 1H), 8.31
(d, J: 5.4 Hz, 1H), 7.33 (dd,
J: 8.5, 5.8 Hz, 1H), 7.04
(dd, .1: 8.4, 6.8 Hz, 1H),
6.99 (d, .1: 5.5 Hz, 1H), 6.88
— 6.74 (m, 2H), 6.64 — 6.53
(Thin ?lm) HREEEEJ" ‘)
(m, 2H), 5.67 (dq, J: 9.8,
“5378 2986
538 1770’ 1736’ calcd for 6.1 Hz, 1H), 4.74 (d, .1: 9.8
16777 15017 F2N207, HZ, 1H), 4.62 — 4.4501],
1196 ’ 557.2094, found, 1H), 3.90 (s, 3H), 3.84 (s,
7 557.2091 3H), 2.38 (s, 3H), 2.27 (s,
3H), 1.25 (d, J : 6.2 Hz,
3H), 0.98 (d, J: 7.2 Hz,
19F NMR (376 MHz, CDC13)
—112.97, -11743.
1H NMR (400 MHz, CDC13)
8.43 — 8.35 (m, 1H), 8.31
(d, .1: 5.4 Hz, 1H), 7.33 (dd,
SI (m/z) J= 8.6, 5.7 Hz, 1H), 7.19 —
(Thin ?lm) ([M+H]+) 7.07 (m, 1H), 7.00 (d, J: 5.5
3377, 2983, Hz, 1H), 6.90 4 6.74 (m,
calcd for
539 1771,1738, 4H), 5.68 (dq,./: 12.0, 6.1
C H PM)
1677, 1502, 54§81§g4? 1,6111% Hz, 1H), 4.62 (d, J = 9.9 Hz,
1201 5451896 ° 1H), 4.61 44.49 (m, 1H),
' 3.90 (s, 3H), 2.38 (s, 3H),
2.28 (s, 3H), 1.27 (d, J: 6.1
Hz, 3H), 1.00 (d, .1: 7.2 Hz,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No, (CC) (cm'l) (1H, 13C. 191:)
1H NMR (300 MHz, CDC13)
8.43 (d, .1: 8.0 Hz, 1H),
8.31 (d, .7: 5.4 Hz, 1H), 7.37
HRMS-ESI (m/Z) 4 7.21 (m, 5H), 7.24 4 7.14
(Thin ?lm) ([M+H]+) (m, 1H), 6,98 (d, J = 5.5 Hz,
3388,2985, 1H), 0.89 4 0.84 (m, 1H),
calcd for
540 1771,1737, 0.79—0.72 (m, 1H), 5.904
C H“ FN7O
1079, 1572, 5092120382- 18301610 5.72 (m, 1H), 4.50 (dq, J =
1508,1452 ‘ 1 ’ 81,711 Hz, lH),4.4l (01,7:
509.2078
.0 Hz, 1H), 3.89 (s, 3H),
2.38 (s, 3H), 2.24 (s, 3H),
1.24 (01, .1: 0.2 Hz, 3H), 1.00
(d, J : 7.2 Hz, 3H).
1H NMR (400 MHz, CDCL.)
8,42 (d, J: 8.2 Hz, 1H),
8.31 (dd,J= 5.5, 1.2 Hz,
1H), 7.29 4 7.17 (m, 3H),
7.07 4 0.89 (m, 3H), 0.87
HRMS-ESI (m z)
(dd, J: 8.0, 1.7 Hz, 1H),
(Thin ?lm) 0.80 4 0.72 (m, 1H), 5.75
3378, 2984, calcd for (dq, .1: 9.7, 0.1 Hz, 1H),
1771, 1737, C28H29FZNZO6: 4.02 4 4.50 (m, 1H), 4.39 (d,
1679, 1509 527.1988, found, J: 9.8 Hz, 1H), 3.89 (s, 3H),
527. 1975 2.38 (s, 3H), 2.25 (s, 3H),
1.26—1.21(m,3H), 1.01 (d,
J = 7.2 Hz, 3H).
”P NMR (370 MHz, CDC13)
4115.07, -118.89.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H. 13C. 191:)
1H NMR (400 MHz. CDC13)
8.48 4 8.36 (m. 1H). 8.29
(d. J: 5.6 Hz. 1H). 7.26 4
7.21 (m. 1H). 7.20 — 7.16 (m.
2H). 7.07 (d. .1: 7.9 Hz.
2H). 6.96 (d. .1: 5.5 Hz.
. HRMSESI!” Z) 1H). 6.84 (dd. J: 8.1. 1.9
(Thm ?lm) ([M+H] ) Hz 1H) 6 74 (dd J = 11 3
3390. 2984. 1 1 1 .1 1 1
calcd for 2.2 Hz.
542 $1772 1H). 5.83 , 5.75 (m..
3:16787 15087 C29H32FN206, 1H). 4.63 — 4.50 (m, 1H).
141152 1 523.2239. found. 4.37 (d. J: 10.1 Hz. 1H).
1 3.86 (s. 3H). 2.37 (s. 3H).
2.27 (s. 3H). 2.22 (s, 3H).
1.24 (d. J: 6.1 Hz. 3H). 1.00
(d. .1: 7.2 Hz. 3H).
191: NMR (376 MHz. CDC13)
-11902.
1H NMR (400 MHz. CDC13)
8.42 (d. J: 7.9 Hz. 1H).
8.31 (d. .1: 5.4 Hz. 1H). 7.24
(dd. J = 9.6. 5.7 Hz. 1H).
7.17 (t. J: 7.9 Hz. 1H). 6.99
(d. .1: 5.5 Hz. 1H). 6.88 4
(Thin ?lm) @5451??? 7) 6.82 (m. 3H). 6.75 (dd.J:
11.3. 2.2 Hz. 1H). 5.72 (dq.J
3384 2983
: 9.8. 6.1 Hz. 1H). 4.63 (d. .1
543 17721 17371 calcd for
16791 15911 C29H31F2N206. : 10.0 Hz. 1H). 4.62
4 4.51
15071 14521 541.2145. found. (m. 1H). 3.89 (s. 3H). 2.39
1 38 (3. 3H). 2.38 (s. 3H). 2.24 (s.
3H). 1.26 (d. J: 6.1 Hz.
3H). 1.05 (d. J: 7.2 Hz.
191: NMR (376 MHz. CDC13)
—116.51.—118.10.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H. 13C. 191:)
1H NMR (400 MHz. CDC13)
8.45 4 8.39 (m. 1H). 8.31
, (61.7: 5.5 Hz. 1H). 7.324
. HRMS'ESIEW) 7.20 (m. 2H). 6.99 (d. J: 5.5
£1111“ ?lm) ([M+H] )
Hz, 1H). 6.88 4 6.84 (m.
17:11:39 calcd for 1H). 6.84 4 6.73 (m. 3H).
16787 15047 C28H23F3N206; 5.85 — 5.74-(111. 1H). 4.70 (d.
1453’ 14.321 545.1894; found. J: 9.9 Hz. 1H). 4.63 44.52
1 ‘ 545.1885 (m. 1H). 3.89 (s. 3H). 2.38
(s. 3H). 2.25 (s. 3H). 1.27 (d.
J: 6.1 Hz. 3H). 1.04 (d. J:
7.2 Hz. 3H).
1H NMR (500 MHZ. CDC13)
8.41 (s. 1H). 8.32 (d../:
.5 Hz. 1H). 7.31 4 7.27 (m.
2H). 7.22 (t. J: 7.7 Hz. 2H).
7.17 (d. .1: 8.1 Hz. 2H). 7.15
4 7.10 (m. 1H). 7.09 (d. .1:
7.9 Hz. 2H). 6.99 (d. J: 5.5
. Hz. 1H). 5.79 (dq. J: 10.1.
$172“ $191312) 6.1 Hz. 1H). 4.57 4 4.47 (m.
1770117347 1H). 4.01 (d.J= 10.1 Hz.
1675’ 1508’ ESIMS m z 4912 1H). 3.90 (s. 3H). 2.38 (s.
1451’ 1309’ ([M+H] ) 3H). 2.28 (s. 3H). 1.24 (d. .1
1 7 :62 Hz. 3H). 0.88 (d.J=
1200. 1174.
7 2 HZ 3H)
1046.907. ' 1 '
802.730. 6
C NMR (126 MHz.
5172.24. 168.91.
162.24. . 146.64.
141.73. 141.57. 138.27.
137.43. 136.47. 129.44.
128.46. 127.99. 126.56.
109.68. 73.36. 57.53.
56.27. 47.83, 20.97. 20.75.
19.24. 17.92.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz, CDC13)
8.42 (s, 1H), 8.32 (d,./:
.4 Hz, 1H), 7.29 4 7.23 (m,
4H), 7.18 (td, J: 6,0, 2.8
Hz, 3H), 7.04 (d, J: 7.9 Hz,
2H), 6.99 (d, .1: 5.5 Hz,
1H), 5.79 (dq, J= 98,62
(Thin ?lm) Hz, 1H), 4.57 — 4.49 (m,
3381, 2982, 1H), 4.02 (d, .1: 9.9 Hz,
1770, 1734, 1H), 3.90 (s, 3H), 2.38 (s,
g; 1675, 1507, ESHXSIZ’Hai‘)“ 3H), 2.25 (s, 3H), 1.23 (d, J
546 1435, 1309, : 6.2 Hz, 3H), 0.93 (d, .7:
1199, 1174, 7.2 Hz, 3H).
1045,907,
804, 729, 13C NMR (126 MHz,
699 CDC13) 5 172.23, 168.92,
162.25, 159.41, 146.64,
141.59, 138.34, 137.44,
136.15, 129.13, 128.72,
, 127.99, 126.77,
10968, 73.38, 57.41,
56.28, 47.87, 20.94, 20.76,
19.25, 18.00,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \\ MP IR NMR
No. (0C) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz, CDC13)
8.41 (s, 1H), 8.32 (01,7:
.4 Hz, 1H), 7.23 (dd, J :
8.7, 5.3 Hz, 2H), 7.18 — 7.13
(m, 2H), 7.05 (d, J = 7.8 Hz,
2H), 7.01 i 0.93 (m, 3H),
.74 (dq, J: 9.0, 02 Hz,
1H), 4.58 — 4.50 (m, 1H),
(Thin ?lm) 4.01 (d, .1: 9.0 Hz, 1H), 3.90
3380, 2982, (s, 3H), 2,38 (s, 3H), 2.20 (s,
1770, 1735, 3H), 1.22 (d, J = 0.2 Hz,
1070, 1507, ESHXSAZ’Hz?fgl 3H), 0,94 (d, .1: 7.2 Hz,
547 1451, 1310, 3H).
\ 1200, 1175,
1158,1047, 13C1\11\4R(1201\4Hz,
908, 810, CDC13) 5 , 108.91,
709, 729 102.20, 101.04 (d, J = 245.3
Hz), 159.43, 140.03,
, 138.05, 137.45,
137.32(d,J=3.3 Hz),
130.34, 129.50 (d, J=7.8
Hz), 129.22, 127.94, 115.53
(d,J= 21.3 Hz), 109.70,
73.21, 50.51, 50.28, 47.85,
.94, 20.75, 19.15, 17.99.
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H. 13C, 191:)
1H NMR (500 MHz, CDC13)
8.40 (s, 1H), 8.32 (d,./:
.4 Hz, 1H), 7.33 4 7.23 (m,
6H), 7.23 — 7.17 (m, 1H),
6.99 (d, J: 5.5 Hz, 1H), 6.93
(t, .1 : 8.6 Hz, 2H), 5.76 (dq,
J: 9.9, 6.2 Hz, 1H), 4.55 (p,
J: 7.2 Hz, 1H), 4.05 (d, J:
(Thin ?lm) 9.8 Hz, 1H), 3.90 (s, 3H),
3379, 2983, 2.38 (s, 3H), 1.23 (d, J: 6.2
1770, 1736, Hz, 3H), 0.97 (d, J: 7.2 Hz,
1676, 1509, 3H).
548 ESI??1\S4:HZ]:1)95 ~1
1452, 1310,
1201,1175, 13CN1\4R(1261V1Hz,
1046, 908, CDC13)6 172.17, ,
817, 732, 162.28, 161.59 (d,J:245.0
700 Hz), 159.44, 146.64,
141.48, 141.04, 137.47,
l37.16(d,J:3.4 Hz),
129.60 (d, J: 7.9 Hz),
128.84, 128.02, 127.02,
115.28 21.1 Hz),
109.74, 73.24, 57.00,
56.28, 47.83, 20.75, 19.22,
18.02.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP 1R NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (500 MHz, CDC13)
8.39 (s, 1H), 8.32 (61,]:
.5 Hz, 1H), 7.28 i 7.21 (m,
2H), 7.14 (d, J: 8.2 Hz,
2H), 7.09 (d, J: 7.9 Hz,
2H), 6.99 (d, .1: 5.5 Hz,
1H), 6.95 — 6.89 (m, 2H),
.74 (dq, J: 10.0, 6.2 Hz,
. - 1H), 45844.50 (m, 1H),
$3315“ 3191?; 4.00 (d, J: 10.0 Hz, 1H),
1;,70’ 173 5’ 3.90 (s, 3H), 2.38 (s, 3H),
1676’ 150‘7’ ESIMS m 2 509.1 2.29 (s, 3H), 1.23 (d, J: 6.1
549 1451’ 1436’ ([M+H]+) Hz, 3H), 0,97 (d, J : 71 Hz,
1310,1201,
153;” £28 13C NMR (126 MHz,
7’31 ’ 5172.18, 168.91,
162.27, 161.54 ((1, .1: 2451
Hz), 159.44, 146.63,
141.50, 138.06, 137.48 ((1, J
= 3.6 Hz), 136.65, 129.49
(d, J: 8.3 Hz), 127.86,
115.24 (d, J: 21.3 Hz),
109.73, 73.30, 56.66,
56.28, 47.83, 20.98, 20.75,
19.22, 18.02,
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. \ MP 1R NMR
No. (0C) (cm'l) (1H.1"C,19F)
1H NMR (400 MHz. CDC13)
8.39 (d. .1: 8.1 Hz. 1H).
8.32 (d. J: 5.5 Hz. 1H). 7.34
— 7.22 (m. 5H). 7.20 — 7.14
(m. 1H). 6.99 (d. J: 5.5 Hz.
1H). 6.85 4 6.74 (m. 2H).
.80 (dtd, J: 9.9. 7.3. 6.7.
.4 Hz. 1H). 4.55 (dt.J=
8.1.7.1 Hz. 1H).4.41 (d..]:
$5“ $1221).
.0 Hz. 1H). 3.90 (s. 3H).
238 (s. 3H). 1.27 (d. J: 6.1
” 1 ’ HZ1 3H’ )1 0.92 d.]:7.2H
1770, 1737, Sl32 311‘)” Z”
1676. 1503. ‘
550 ([M+H]+)
145211310”4 13CNMR (126 MHz
‘ 322* i512 CDC13)5172,13. 168.91.
, 162.27. 162.03 (dd.J=
9077 731
168.8. 12.1 Hz). 160.964
159.14 (m). 159.43. 146.64.
141.50. 140.06. 137.46.
129.88 (dd.J= 9.6. 5.6 Hz).
128.60. 128.27. .
124.68 — 124.00 (m). 111.60
(dd. J: 21.3. 3.6 Hz).
. 1045541033
(m). 72.51. 56.28. 49.35.
47.80. 20.75. 18.92. 17.92.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.40 (s, 1H), 8.32 (d,./:
.5 Hz, 1H), 7.25 4 7.16 (m,
3H), 7.05 (d, J: 7.9 Hz,
2H), 6.99 (d, .1: 5.5 Hz,
1H), 6.84 4 6.73 (m, 2H),
.77 (dtd, J: 9.5, 6.5, 5.2
Hz, 1H), 4.59 — 4.51 (m,
(Thin ?lm) 1H), 4.38 (d, .1: 9.8 Hz,
3384, 2983, 1H), 3.90 (s, 3H), 2.38 (s,
1771, 1737, 3H), 2.26 (s, 3H), 1.25 (d, J
1677, 1502, ESHXSAZ’HZ?fm : 6.2 Hz, 3H), 0.96 (d, J :
551 1452, 1310, 72 Hz, 3H).
1201, 1175,
1148, 1049, 13C NMR (126 MHz,
966, 908, CDC13) 5 172.12, 168.92,
732 162.78 — 159.09 (111), 146.64,
141.53, 137.46, 136.96,
136.56, 129.88 ((1, J: 57
Hz), , 128.16, 124.64
((1, J=15,0 Hz),111.52(d,J
:208 Hz), 109.71, 104.49
— 103.84 (m), 72.59, 56.28,
48.90, 47.84, 20.96, 20.75,
18.92, 18.00.
[Annotation] Mel.Chan
None set by an
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Cmpd. MP IR NMR
No. (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.37 (d, .1: 6.0 Hz, 1H),
8.32 (d, J: 5.4 Hz, 1H), 7.28
— 7.18 (m, 3H), 7.00 (d, J:
.5 Hz, 1H), 6.97 — 6.90 (m,
2H), 6.86 4 6.75 (m, 2H),
.76 (dtd, J: 9.7, 6.5, 5.2
Hz, 1H), 4.62 — 4.48 (m,
(Thin ?lm) 1H), 4.39 (d, .1: 9.8 Hz,
3384, 2985, 1H), 3.91 (s, 3H), 2.38 (s,
1770, 1737, , 3H), 1.26 (d, J = 6.1Hz,
1676, 1503, $104184th +5312 3H), 1,00 (d, .1: 7.2 Hz,
552 ([ 1 )
1201, 1175, 3H).
1160, 1148,
966, 847, 13C NMR (126 MHz,
825, 811, CDC13) 5 172.05, 168.91,
732 163.09 — 159.02 (111), 146.63,
141.42, 137.50, 135.78,
12982 (d, J: 8.2 Hz),
124.23 (d,J= 11.3 Hz),
115.42 (d,J= 21.3 Hz),
111.98 4111.29(m), 109.77,
104.80 — 103.42 (m), 72.42,
56.30, 48.69, 47.81, 20.75,
18.93, 18.00.
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
Cmpd. MP IR NMR
No, (CC) (cm'l) (1H, 13C, 191:)
1H NMR (400 MHz, CDC13)
8.41 (d, .1: 7.4 Hz, 1H),
8.31 (d, J: 5.4 Hz, 1H), 7.32
— 7.20 (m, 4H), 7.19 — 7.11
(m, 1H), 7.12 — 7.02 (m, 2H),
HRMS—ESI (m z) 6.98 (d, .1: 5.5 Hz, 1H), 6.90
([M+H]+) (dd, J = 9.6, 8.1 Hz, 1H),
.76 (dq, J: 100, 6.2 Hz,
calcd for
553 1H), 4.59—4.45 (m, 1H),
C28H30FNZOO’ 3 99
3‘ (d J: 10 1 Hz
509.2088; found, y ', ’ 1H) 1
3.88 (s, 5H), 2.37 (s, 3H),
509 2074'
2.22 (d, .1: 2.0 Hz, 3H), 1.23
(d, J: 6.1 Hz, 3H), 0,90 (d,
J = 7.2 Hz, 3H).
”P NMR (3 76 MHz, CDC13)
—120. 17.
'H NMR (400 MHz, CDC13)
8.40 (s, 1H), 8.31 (d, J:
.4 Hz, 1H), 7.32 - 7,23 (m,
1H), 7.11 — 7.01 (m, 2H),
6.99 (d, J: 5.5 Hz, 1H), 6.88
(t, J: 9.3 Hz, 1H), 6.58 (td,
HRMS—ESI (m z) .I: 8.3, 2.5 Hz, 1H), 6.52
([M+H]+) (dd, J 2 109, 2.5 Hz, 1H),
.74 (dq, J: 10.1, 6.2 Hz,
calcd for
554 1H), 4.55 (dq, .1: 8.1, 7.2
C)‘)H11F7N)O7
557 20399,T fdund HZ’ 1H)” 4‘46 (d’ J : [0'1
‘557 21091 ’ Hz, 1H), 3.90 (s, 3H),3.77
' (s, 3H), 2,38 (s, 3H), 2.21 (d,
.1: 1.9 Hz, 3H), 1.20 (d, J:
6.1 Hz, 3H), 0.99 (d, J = 7.1
Hz, 3H),
191: NMR (3 76 MHz, CDC13)
-113,46,-120,45.
. I\0. — Compound Number
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
Table 3. Biological Testing Rating Scale
Rating Table for Fungal Pathogens
Not Tested
No Activity Observed in the Reported
Assay
Table 4. Biological Activity — PUCCRT and SEPTTR Disease Control in High and Low
Volume Applications
HV activity at 100 ppm LV activity at 121.5 g/H
* SEPTTR>X< PUCCRT"< SEPTTR*
' 1DP* 3DC"< lDP* 3DC* 3DC"<
CCCCCC
AAACCCC
BADCCCC
AAAABAA
DABCCCC
_DAACCCC
_AAACCCC
_BAACCCC
ADAACCCC_C
107 ABAACCCC
109 BDDBCCCC
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] an
Unmarked set by Mel.Chan
VC .mVDDDBA W mm C paWR T VCmm
111 A WWW:0PWT LWCC MWCCW mm
113 CC
114 .A mwnAABBA A HWCCCC-CCa?gmmWoT.C
AB AA C/CC CC
C CC/C
121 AA BB AA
—A124 AABAAA C/CC/CCCCC CCCCC
B D C
130 B BD AA C/CC C/CC
”‘B131135137 BC ADAAADBAC CCCCC
C C A BA CC/CCCCCCCCAA CCCCCCCCBA
142 C C CC AA AA AA
145 CC CCCCC
.CC BA
148 CC CC CC BA BA .BA AABBAAAA
ation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
mmam.mVCC W. mm MSCCCCCConWT HR mm W
TmWCCCC aC
49 LWBAVC MWBA 1
150 PCC QSAAAAAmydo“ HWAAAA
189 C C CCCCC CCC A B AABAA BAA
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
HV activity at 100 Rpm LV activity at 121.5 g/H
"< SEPTTR* PUCCRT"< SEPTTR*
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
ionNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
WC paWR.mVBDBABCDAA W mm onWTmwnADDADCBAA LWCCCCCCCCCVC mmMWCCCCCCCCCW a mydo“ C T
333333333 00009999999 WBAAAACBAA 0090123456
BA CCCCCCCC HWCCCCCCCCCCCC
AB CC
AA CC/CC/CC CC
44444444444 00111111111 0090123456700 AABACABAAAA DBDDAD CC/CC/CCCCCCCCCCCCC AAABACABABBAB CCCCCCCCCCCCC
DD CC
44 22 5/0 AAA AAA CCCCCCCCCCCCC/CC/CCC CC/CC/CC/CCCCCCCCCCCCC/CC/CCC CC/CCC BAD CCC
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
WC .mWDDD mm W
CmR mSBBonWT VC aCHR WoT
700 WBB mmBAB,x. .WTCC.1*W mm 22 mSCCCCCC 44 LWCC HWCCCC
463 C C C C/ D D D B
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
mm W. mm W mm
CpawR VC aCHR 5m
44 6/0 45 PCC .mAPCC CComWTmmCCCC .x./ MATAD éADnnD (0.VTHWADBB
55 00 01 CC CC CC CC DBB AAA AAB
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
ation] Mel.Chan
Unmarked set by Mel.Chan
VC W M W a
CpaWR OFmm VCmm awnWT
503 HWCC .m*TCC LWAAAB
—‘—‘510 C
51] C
512 mWCCCCCCCCCCC MWBBDDDDABABD HWDABDDDABADD
C B D D
CC DA DA DA
CC AB AB AB
—‘—‘—525 CC
)] C CCCCCCCCCCC
532 C BDAAABBBBDAA
C AA A BBAAAAAAAAAAA
CC AA AB AA
540 C C CCC AAA BBB AAA
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
HV activity at 100 ppm LV activity at 121.5 g/H
PUCCRT* SEPTTR* * SEPTTR*
54] C C C C A B A A
542 C C C C A B A A
C C C C A A A A
C C C C A A A A
C C A
C A
C C C C A A A A
C C C C A A A A
C C C C A A A A
*Cmpd. No. — Compound Number
*PUCCRT * Wheat Brown Rust (Puccima lri/icma)
*SEPTTR * Wheat Leaf Blotch (Zyvnriois'epz‘ariu trilici)
*lDP — 1 Day tant
*3DC , 3 Day Curative
*g/H , Grams Pcr Hoctarc
*ppm — Parts Per Million
Table 5. Biological ty — Disease Control at 100 ppm
ALTESO* CERCBE"< COLLLA* LEPTNO"<
>>CUD>CU
I>>>>>>>>>
50> >> >>>>>>>>>>> >>>>>>>>>>>
ation] Mel.Chan
None set by Mel.Chan
[Annotation] an
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
ALTESO"< CERCBE’:< COLLLA* LEPTNO"<
i>lii>>>|>>>A A
A A
A A
A A
A A
>lA A A A
>iA A A A
A A
mepd. No. , Compound Number
CALTESO — Tomato Early Blight (Alfemaria solani)
*CERCBE 7 Leaf Spot of Sugar Beets (Cercospom be?co/a)
*COLLLA 7 Cucumber Anthracnoso (( YONG/()H‘IICZIH? Ingmar/71297)
*LEPTNO — Wheat Glume Blotch (Lepfosphaeria nodomm)
*lDP — 1 Day Protectant
Table 6. Biological Activity — Disease Control at 100 ppm
PYRIOR* RHYNSE>X< VENTTN*
Cmpd. No. lDP*
92 C A C
139 A A A
140 A C A
141 A A A
142 A A A
145 A A A
146 A A A
148 A A A
150 A A A
167 A A C
171 A A C
174 A A B
l76 A A A
199 A A C
204 A A C
464 A A A
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
ed set by Mel.Chan
PYRIOR"< RHYNSE>X< VENTIN’:<
Cmpd. No. 1DP"<
468 A A A
472 A A A
475 A A B
524 A A A
528 A A A
532 C A C
*Cmpd. N0, 4 Compound Number
*PYRIOR —‘ Rice Blast (Pyriczz/aria oryzae)
*RHYNSE — Barley Scald (R173 ‘I7colsp0rizmz 's)
iVENTIN 4 Apple Scab (WWW/'0 a/l's)
ilDP — 1 Day Protectant
Table 7. Biological Activity — Disease Control at 25 ppm
PHAKPA*
Cmpd. N0. lDP”< 3DC’1<
139 A B
140 B D
141 A B
142 A B
92 B B
145 A B
146 A B
148 A B
150 A A
158 A B
l67 A B
169 A D
171 A B
173 B D
174 A B
175 B D
176 B B
199 A B
204 A B
207 B D
208 A B
209 A B
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by an
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
PHAKPA>X<
Cmpd. NO. 1DP* 3DC*
210 A D
211 A B
212 B D
213 A B
464 A A
468 A B
472 A B
475 A B
493 D D
494 D D
495 B D
496 B D
497 D D
498 A B
499 B B
500 A B
501 B B
502 B D
503 A D
504 B D
505 D D
506 D D
507 D D
508 B D
509 D D
510 B D
511 D D
512 D D
513 D D
514 D D
515 D D
516 B D
517 B D
518 B D
519 D B
520 D D
521 B D
522 B D
523 A B
[Annotation] Mel.Chan
None set by Mel.Chan
[Annotation] Mel.Chan
MigrationNone set by Mel.Chan
[Annotation] Mel.Chan
Unmarked set by Mel.Chan
PHAKPA*
Cmpd. No. 1DP* 3DC*
524 A B
525 A B
526 A D
527 A B
528 A B
529 A B
530 A B
531 A B
532 A B
533 A B
534 A B
535 B D
536 A B
537 A B
538 B B
539 A B
540 A B
541 A B
542 B D
543 A B
544 A B
545 B D
546 A B
547 A B
548 A D
549 B D
550 A B
551 A B
552 A B
553 B D
554 B D
*Cmpd. No. , Compound Number
*PHAKPA , Asian Soybean Rust (Pha/copsom pac/7VW‘I71'ZI')
*lDP — 1 Day tant
*3DC , 3 Day Curative
Claims (3)
1. A compound which is chosen from Compound Number ure 1004849615 O CH3 H3C O O CH3 141 H N O O CH3 H3C O 142 O CH3 N O O CH3 O CH3 H3C O O CH3 149 H N O O CH3 O CH3 H3C O O F O CH3 O CH3 194 N N O O CH3 H3C O CH3 O Cl O CH3 206 N O CH3 O CH3 OH F O CH3 387 N O O CH3
2. A ition including at least one of the compounds of claim 1 and a phytologically acceptable carrier material.
3. The composition of claim 2 further comprising at least one of the compounds of claim 1 and r pesticide including fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof. 1004849615
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462098122P | 2014-12-30 | 2014-12-30 | |
US201462098120P | 2014-12-30 | 2014-12-30 | |
NZ732641A NZ732641A (en) | 2014-12-30 | 2015-12-18 | Picolinamide compounds with fungicidal activity |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ748767A NZ748767A (en) | 2023-08-25 |
NZ748767B2 true NZ748767B2 (en) | 2023-11-28 |
Family
ID=
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