JP3566955B2 - 新規ルテニウム錯体およびこれを触媒として用いるアルコール化合物の製造方法 - Google Patents
新規ルテニウム錯体およびこれを触媒として用いるアルコール化合物の製造方法 Download PDFInfo
- Publication number
- JP3566955B2 JP3566955B2 JP2002248058A JP2002248058A JP3566955B2 JP 3566955 B2 JP3566955 B2 JP 3566955B2 JP 2002248058 A JP2002248058 A JP 2002248058A JP 2002248058 A JP2002248058 A JP 2002248058A JP 3566955 B2 JP3566955 B2 JP 3566955B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- group
- same
- different
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 alcohol compound Chemical class 0.000 title claims description 129
- 239000012327 Ruthenium complex Substances 0.000 title claims description 68
- 238000004519 manufacturing process Methods 0.000 title claims description 21
- 239000003054 catalyst Substances 0.000 title description 58
- 239000001257 hydrogen Substances 0.000 claims description 100
- 229910052739 hydrogen Inorganic materials 0.000 claims description 100
- 125000004432 carbon atom Chemical group C* 0.000 claims description 86
- 150000002430 hydrocarbons Chemical group 0.000 claims description 80
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 150000001875 compounds Chemical group 0.000 claims description 38
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 33
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 29
- 239000002585 base Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000000129 anionic group Chemical group 0.000 claims description 12
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229940126062 Compound A Drugs 0.000 claims description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- WREFXNGPCLHVSW-UHFFFAOYSA-N (4-diphenylphosphanyl-3-methylpentan-2-yl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 WREFXNGPCLHVSW-UHFFFAOYSA-N 0.000 claims description 5
- WDYGPMAMBXJESZ-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical group C1=CC(OC)=CC=C1C(N)(C(N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-UHFFFAOYSA-N 0.000 claims description 5
- BQUNSIYVDVZZEA-UHFFFAOYSA-N 4-bis(3,5-dimethylphenyl)phosphanylpentan-2-yl-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)CC(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 BQUNSIYVDVZZEA-UHFFFAOYSA-N 0.000 claims description 5
- ZHIOKCFUZLQANC-UHFFFAOYSA-N 4-bis(4-methylphenyl)phosphanylpentan-2-yl-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)CC(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZHIOKCFUZLQANC-UHFFFAOYSA-N 0.000 claims description 5
- ATHCDBOOSFQXPT-UHFFFAOYSA-N [3-bis(3,5-dimethylphenyl)phosphanyl-1,3-diphenylpropyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(P(C(CC(P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=C(C)C=C(C)C=2)=C1 ATHCDBOOSFQXPT-UHFFFAOYSA-N 0.000 claims description 5
- LVYGXVVRZGNPMS-UHFFFAOYSA-N [4-bis(4-methylphenyl)phosphanyl-3-methylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LVYGXVVRZGNPMS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- WPEXKMAYUSUXIF-UHFFFAOYSA-N (3-diphenylphosphanyl-1,3-diphenylpropyl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)CC(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 WPEXKMAYUSUXIF-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- GFGZHQCWZWATGF-UHFFFAOYSA-N [3-bis(4-methylphenyl)phosphanyl-1,3-diphenylpropyl]-bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)CC(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 GFGZHQCWZWATGF-UHFFFAOYSA-N 0.000 claims description 4
- YOHVTQHWOPUYGB-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3-methylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 YOHVTQHWOPUYGB-UHFFFAOYSA-N 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 150000001450 anions Chemical group 0.000 claims description 4
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical group C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 claims description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- KORFDERLECDIGW-UHFFFAOYSA-N (3-diphenylphosphanyl-2-methyl-1,3-diphenylpropyl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(C)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 KORFDERLECDIGW-UHFFFAOYSA-N 0.000 claims description 3
- 235000013847 iso-butane Nutrition 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims 2
- REBJSIWYFWFTMF-UHFFFAOYSA-N C1(=CC=C(C=C1)P(C(C(C(C1=CC=CC=C1)P(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C)C1=CC=CC=C1)C1=CC=C(C=C1)C)C.C1(=CC=CC=C1)P(C(C(C(C1=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)C)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)P(C(C(C(C1=CC=CC=C1)P(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C)C1=CC=CC=C1)C1=CC=C(C=C1)C)C.C1(=CC=CC=C1)P(C(C(C(C1=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)C)C1=CC=CC=C1)C1=CC=CC=C1 REBJSIWYFWFTMF-UHFFFAOYSA-N 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 149
- 229910052717 sulfur Inorganic materials 0.000 description 134
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 102
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 67
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 48
- 229910052786 argon Inorganic materials 0.000 description 47
- VURFVHCLMJOLKN-UHFFFAOYSA-N Diphosphine Natural products PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 46
- 230000003287 optical effect Effects 0.000 description 41
- WDYGPMAMBXJESZ-GOSISDBHSA-N (2r)-1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)([C@H](N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-GOSISDBHSA-N 0.000 description 38
- 239000002904 solvent Substances 0.000 description 31
- 239000003446 ligand Substances 0.000 description 29
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000011521 glass Substances 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- 239000000758 substrate Substances 0.000 description 22
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N 4-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 description 21
- HBIHVBJJZAHVLE-UHFFFAOYSA-L dibromoruthenium Chemical compound Br[Ru]Br HBIHVBJJZAHVLE-UHFFFAOYSA-L 0.000 description 20
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 19
- 238000004817 gas chromatography Methods 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 9
- WDYGPMAMBXJESZ-SFHVURJKSA-N (2s)-1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)([C@@H](N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-SFHVURJKSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical class [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 238000010926 purge Methods 0.000 description 7
- 238000004445 quantitative analysis Methods 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical group CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 6
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 6
- 229910052707 ruthenium Inorganic materials 0.000 description 6
- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000000852 hydrogen donor Substances 0.000 description 5
- 125000003884 phenylalkyl group Chemical group 0.000 description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 4
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- VEAFKIYNHVBNIP-UHFFFAOYSA-N 1,3-Diphenylpropane Chemical class C=1C=CC=CC=1CCCC1=CC=CC=C1 VEAFKIYNHVBNIP-UHFFFAOYSA-N 0.000 description 4
- DAVFJRVIVZOKKS-UHFFFAOYSA-N 2-(4-methylphenyl)ethanol Chemical compound CC1=CC=C(CCO)C=C1 DAVFJRVIVZOKKS-UHFFFAOYSA-N 0.000 description 4
- GDWRKZLROIFUML-UHFFFAOYSA-N 4-phenylbutan-2-ol Chemical compound CC(O)CCC1=CC=CC=C1 GDWRKZLROIFUML-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000004210 ether based solvent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000003303 ruthenium Chemical class 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- FWXAUDSWDBGCMN-ZEQRLZLVSA-N chiraphos Chemical compound C=1C=CC=CC=1P([C@@H](C)[C@H](C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-ZEQRLZLVSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 3
- 238000011002 quantification Methods 0.000 description 3
- 150000003304 ruthenium compounds Chemical class 0.000 description 3
- PONXTPCRRASWKW-UHFFFAOYSA-N 1,2-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)C(N)C1=CC=CC=C1 PONXTPCRRASWKW-UHFFFAOYSA-N 0.000 description 2
- UABXUIWIFUZYQK-UHFFFAOYSA-N 1-(furan-2-yl)ethanol Chemical compound CC(O)C1=CC=CO1 UABXUIWIFUZYQK-UHFFFAOYSA-N 0.000 description 2
- JMSUNAQVHOHLMX-UHFFFAOYSA-N 1-cyclohexylethanol Chemical compound CC(O)C1CCCCC1 JMSUNAQVHOHLMX-UHFFFAOYSA-N 0.000 description 2
- PPHIIIRFJKDTLG-UHFFFAOYSA-N 1-pyridin-2-ylethanol Chemical compound CC(O)C1=CC=CC=N1 PPHIIIRFJKDTLG-UHFFFAOYSA-N 0.000 description 2
- WUNFIVTVJXZDDJ-UHFFFAOYSA-N 1-thiophen-2-ylethanol Chemical compound CC(O)C1=CC=CS1 WUNFIVTVJXZDDJ-UHFFFAOYSA-N 0.000 description 2
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical group CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 2
- SHOJXDKTYKFBRD-UHFFFAOYSA-N 4-Methyl-3-penten-2-one, 9CI Chemical group CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 2
- CTYPJIUQROQJBG-UHFFFAOYSA-N 4-diphenylphosphanylpentan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)CC(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 CTYPJIUQROQJBG-UHFFFAOYSA-N 0.000 description 2
- SAOXPNBHKSWHGW-UHFFFAOYSA-N 4-methylpent-3-en-2-ol Chemical compound CC(O)C=C(C)C SAOXPNBHKSWHGW-UHFFFAOYSA-N 0.000 description 2
- ULBXWWGWDPVHAO-UHFFFAOYSA-N Chlorbufam Chemical compound C#CC(C)OC(=O)NC1=CC=CC(Cl)=C1 ULBXWWGWDPVHAO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- OYJLCOSEYYZULE-UHFFFAOYSA-N [1-[2-(trifluoromethylsulfonyloxy)naphthalen-1-yl]naphthalen-2-yl] trifluoromethanesulfonate Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3OS(=O)(=O)C(F)(F)F)=C(OS(=O)(=O)C(F)(F)F)C=CC2=C1 OYJLCOSEYYZULE-UHFFFAOYSA-N 0.000 description 2
- UXHGOSLRMLRAKR-UHFFFAOYSA-N [3-bis(3,5-dimethylphenyl)phosphanyl-2-methyl-1,3-diphenylpropyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 UXHGOSLRMLRAKR-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- GYZZZILPVUYAFJ-UHFFFAOYSA-N phanephos Chemical compound C1CC(C(=C2)P(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C2CCC2=CC=C1C=C2P(C=1C=CC=CC=1)C1=CC=CC=C1 GYZZZILPVUYAFJ-UHFFFAOYSA-N 0.000 description 2
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- FFYPJCDZTCDMJC-UHFFFAOYSA-N (2-benzyl-2-propan-2-ylpentyl)benzene Chemical compound C1(=CC=CC=C1)CC(CC1=CC=CC=C1)(C(C)C)CCC FFYPJCDZTCDMJC-UHFFFAOYSA-N 0.000 description 1
- PAORVUMOXXAMPL-VIFPVBQESA-N (2r)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride Chemical compound CO[C@@](C(Cl)=O)(C(F)(F)F)C1=CC=CC=C1 PAORVUMOXXAMPL-VIFPVBQESA-N 0.000 description 1
- NXKMRSSEICPSAD-UHFFFAOYSA-N (3-diphenylphosphanyl-2,2-dimethyl-1,3-diphenylpropyl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(C)(C)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 NXKMRSSEICPSAD-UHFFFAOYSA-N 0.000 description 1
- AUBNYIIOYJCWHG-UHFFFAOYSA-N (4-diphenylphosphanyl-3,3-diethylpentan-2-yl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(CC)(CC)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 AUBNYIIOYJCWHG-UHFFFAOYSA-N 0.000 description 1
- CQBYZZOJPDVOOR-UHFFFAOYSA-N (4-diphenylphosphanyl-3,3-dimethylpentan-2-yl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C)(C)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 CQBYZZOJPDVOOR-UHFFFAOYSA-N 0.000 description 1
- NGRDMVYBXASJNI-UHFFFAOYSA-N (4-diphenylphosphanyl-3-ethyl-3-methylpentan-2-yl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C)(CC)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 NGRDMVYBXASJNI-UHFFFAOYSA-N 0.000 description 1
- BYBKWMOWKHHENJ-UHFFFAOYSA-N (4-diphenylphosphanyl-3-ethylpentan-2-yl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(CC)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 BYBKWMOWKHHENJ-UHFFFAOYSA-N 0.000 description 1
- CXVHFAAZDBQQEE-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)-3-phenylpropane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)(C=1C=CC(OC)=CC=1)C(N)CC1=CC=CC=C1 CXVHFAAZDBQQEE-UHFFFAOYSA-N 0.000 description 1
- RYEKIQZUTHKUKD-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)-4-methylpentane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)(C(N)CC(C)C)C1=CC=C(OC)C=C1 RYEKIQZUTHKUKD-UHFFFAOYSA-N 0.000 description 1
- FUIAQGXJJSEAJH-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)propane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)(C(C)N)C1=CC=C(OC)C=C1 FUIAQGXJJSEAJH-UHFFFAOYSA-N 0.000 description 1
- CJLVEEKBJGYLAZ-UHFFFAOYSA-N 1,1-dinaphthalen-1-ylpropane-1,2-diamine Chemical compound C1=CC=C2C(C(N)(C=3C4=CC=CC=C4C=CC=3)C(N)C)=CC=CC2=C1 CJLVEEKBJGYLAZ-UHFFFAOYSA-N 0.000 description 1
- OWUQWDCZCOJEKU-UHFFFAOYSA-N 1,1-diphenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)(C(N)C)C1=CC=CC=C1 OWUQWDCZCOJEKU-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RJAYPPWOMFFZAB-UHFFFAOYSA-N 1-(3-methyl-1-naphthalen-1-ylbut-1-enyl)naphthalene Chemical group C(C)(C)C=C(C1=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 RJAYPPWOMFFZAB-UHFFFAOYSA-N 0.000 description 1
- VVMNQWITSJDEQW-UHFFFAOYSA-N 1-(4-methyl-1-naphthalen-1-ylpent-1-enyl)naphthalene Chemical group C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)=CCC(C)C)=CC=CC2=C1 VVMNQWITSJDEQW-UHFFFAOYSA-N 0.000 description 1
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical group CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 1
- 229940087189 2,2,2-trifluoroacetophenone Drugs 0.000 description 1
- JITRCUREWFPMMJ-UHFFFAOYSA-N 2,3-dimethylbutane-1,1-diamine Chemical compound CC(C)C(C)C(N)N JITRCUREWFPMMJ-UHFFFAOYSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 description 1
- DKASDMAHYNJHHX-UHFFFAOYSA-N 3-(1-diphenylphosphanylethyl)hexan-2-yl-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(CCC)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 DKASDMAHYNJHHX-UHFFFAOYSA-N 0.000 description 1
- MDXFTQJULQIQCK-UHFFFAOYSA-N 3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]hexan-2-yl-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(CCC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 MDXFTQJULQIQCK-UHFFFAOYSA-N 0.000 description 1
- GKZZWXWHUFNYRY-UHFFFAOYSA-N 3-[1-bis(4-methylphenyl)phosphanylethyl]hexan-2-yl-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(CCC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 GKZZWXWHUFNYRY-UHFFFAOYSA-N 0.000 description 1
- FWXAUDSWDBGCMN-UHFFFAOYSA-N 3-diphenylphosphanylbutan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-UHFFFAOYSA-N 0.000 description 1
- UGYCWJKLMOREKO-UHFFFAOYSA-N 3-methyl-1,1-diphenylbutane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)(C(N)C(C)C)C1=CC=CC=C1 UGYCWJKLMOREKO-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- PEXFGZJGEXXSBE-UHFFFAOYSA-N 4-methyl-1,1-diphenylpentane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)(C(N)CC(C)C)C1=CC=CC=C1 PEXFGZJGEXXSBE-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- LLUFBKROUYWLMW-UHFFFAOYSA-L C12=CC=C(CC1)C2.[Ru](Cl)Cl Chemical compound C12=CC=C(CC1)C2.[Ru](Cl)Cl LLUFBKROUYWLMW-UHFFFAOYSA-L 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N CC1CCCC1 Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
- IOPQYDKQISFMJI-UHFFFAOYSA-N [1-[2-bis(4-methylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methylphenyl)phosphane Chemical group C1=CC(C)=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IOPQYDKQISFMJI-UHFFFAOYSA-N 0.000 description 1
- AAMCOZWAABMDIZ-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-1-phenyl-2-propan-2-ylpentyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C(C)C)(CCC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 AAMCOZWAABMDIZ-UHFFFAOYSA-N 0.000 description 1
- SBNVVWCRXYIJKH-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-1-phenyl-2-propylpentyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(CCC)(CCC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 SBNVVWCRXYIJKH-UHFFFAOYSA-N 0.000 description 1
- RHLYTTHEUBUZPM-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-1-phenylbutyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(CC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 RHLYTTHEUBUZPM-UHFFFAOYSA-N 0.000 description 1
- WSVLBKCYINLNGL-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-1-phenylpentyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(CCC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 WSVLBKCYINLNGL-UHFFFAOYSA-N 0.000 description 1
- ZLTBXQBKKDLUCV-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-2-ethyl-1-phenylbutyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(CC)(CC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 ZLTBXQBKKDLUCV-UHFFFAOYSA-N 0.000 description 1
- FFMKXWIQWMYSDN-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-2-ethyl-1-phenylpentyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(CC)(CCC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 FFMKXWIQWMYSDN-UHFFFAOYSA-N 0.000 description 1
- FRAQLEPXOUZWBA-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-2-methyl-1-phenylpentyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C)(CCC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 FRAQLEPXOUZWBA-UHFFFAOYSA-N 0.000 description 1
- AQEQKEWHSPTUFX-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-3-methyl-1-phenylbutyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C(C)C)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 AQEQKEWHSPTUFX-UHFFFAOYSA-N 0.000 description 1
- SZMKBVRBRXRNFK-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-1-phenyl-2-propylpentyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(CCC)(CCC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 SZMKBVRBRXRNFK-UHFFFAOYSA-N 0.000 description 1
- KHTSRJWARDCEEX-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(CC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 KHTSRJWARDCEEX-UHFFFAOYSA-N 0.000 description 1
- GKZUGNSPZBOVMI-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2,3-dimethyl-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C)(C(C)C)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 GKZUGNSPZBOVMI-UHFFFAOYSA-N 0.000 description 1
- KXGRYZVGWIWQOC-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2-ethyl-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(CC)(CC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 KXGRYZVGWIWQOC-UHFFFAOYSA-N 0.000 description 1
- KGZZWGXDEOFHSI-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2-ethyl-1-phenylpentyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(CC)(CCC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 KGZZWGXDEOFHSI-UHFFFAOYSA-N 0.000 description 1
- FVPOOBCSIKOWCN-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2-ethyl-3-methyl-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C(C)C)(CC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 FVPOOBCSIKOWCN-UHFFFAOYSA-N 0.000 description 1
- VXUKVXKDYZWRSS-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2-methyl-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C)(CC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 VXUKVXKDYZWRSS-UHFFFAOYSA-N 0.000 description 1
- WBTDKJGJTWJAQP-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2-methyl-1-phenylpentyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C)(CCC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WBTDKJGJTWJAQP-UHFFFAOYSA-N 0.000 description 1
- NPXANIULGSLJDK-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-3-methyl-1-phenyl-2-propan-2-ylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C(C)C)(C(C)C)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 NPXANIULGSLJDK-UHFFFAOYSA-N 0.000 description 1
- IVOPXXVEFMBQNN-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-3-methyl-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C(C)C)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IVOPXXVEFMBQNN-UHFFFAOYSA-N 0.000 description 1
- BXECUPNQMWUCAM-UHFFFAOYSA-N [2-[diphenylphosphanyl(phenyl)methyl]-1-phenyl-2-propylpentyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(CCC)(CCC)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 BXECUPNQMWUCAM-UHFFFAOYSA-N 0.000 description 1
- VEJAGUNVXLZRPW-UHFFFAOYSA-N [2-[diphenylphosphanyl(phenyl)methyl]-1-phenylbutyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(CC)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 VEJAGUNVXLZRPW-UHFFFAOYSA-N 0.000 description 1
- RMEHYBRNNNMCFH-UHFFFAOYSA-N [2-[diphenylphosphanyl(phenyl)methyl]-1-phenylpentyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(CCC)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 RMEHYBRNNNMCFH-UHFFFAOYSA-N 0.000 description 1
- VMNOCTSCGDOMKW-UHFFFAOYSA-N [2-[diphenylphosphanyl(phenyl)methyl]-2,3-dimethyl-1-phenylbutyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(C)(C(C)C)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 VMNOCTSCGDOMKW-UHFFFAOYSA-N 0.000 description 1
- BWFYFFXWXZBDSI-UHFFFAOYSA-N [2-[diphenylphosphanyl(phenyl)methyl]-2-ethyl-1-phenylbutyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(CC)(CC)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 BWFYFFXWXZBDSI-UHFFFAOYSA-N 0.000 description 1
- WYUFCGKONVLYMX-UHFFFAOYSA-N [2-[diphenylphosphanyl(phenyl)methyl]-2-methyl-1-phenylbutyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(C)(CC)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 WYUFCGKONVLYMX-UHFFFAOYSA-N 0.000 description 1
- LNUCRMPMZYHAGO-UHFFFAOYSA-N [2-[diphenylphosphanyl(phenyl)methyl]-2-methyl-1-phenylpentyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(C)(CCC)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 LNUCRMPMZYHAGO-UHFFFAOYSA-N 0.000 description 1
- ZJOSFSQAMSLVEL-UHFFFAOYSA-N [2-[diphenylphosphanyl(phenyl)methyl]-3-methyl-1-phenyl-2-propan-2-ylbutyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(C(C)C)(C(C)C)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 ZJOSFSQAMSLVEL-UHFFFAOYSA-N 0.000 description 1
- SKHRPWSBFZHUJT-UHFFFAOYSA-N [3-(1-diphenylphosphanylethyl)-3,4-dimethylpentan-2-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C)(C(C)C)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 SKHRPWSBFZHUJT-UHFFFAOYSA-N 0.000 description 1
- FKZWSMNNIQBSMA-UHFFFAOYSA-N [3-(1-diphenylphosphanylethyl)-3-ethyl-4-methylpentan-2-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C(C)C)(CC)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 FKZWSMNNIQBSMA-UHFFFAOYSA-N 0.000 description 1
- LYUFSCPVUFTMBR-UHFFFAOYSA-N [3-(1-diphenylphosphanylethyl)-3-ethylhexan-2-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(CC)(CCC)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 LYUFSCPVUFTMBR-UHFFFAOYSA-N 0.000 description 1
- URTZWVDSVDGQQT-UHFFFAOYSA-N [3-(1-diphenylphosphanylethyl)-3-methylhexan-2-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C)(CCC)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 URTZWVDSVDGQQT-UHFFFAOYSA-N 0.000 description 1
- ZPFNQMRBSLYEKV-UHFFFAOYSA-N [3-(1-diphenylphosphanylethyl)-3-propan-2-ylhexan-2-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C(C)C)(CCC)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 ZPFNQMRBSLYEKV-UHFFFAOYSA-N 0.000 description 1
- AMYQFNWEKFVBHX-UHFFFAOYSA-N [3-(1-diphenylphosphanylethyl)-3-propylhexan-2-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(CCC)(CCC)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 AMYQFNWEKFVBHX-UHFFFAOYSA-N 0.000 description 1
- JRJMHISKSJUQLS-UHFFFAOYSA-N [3-(1-diphenylphosphanylethyl)-4-methyl-3-propan-2-ylpentan-2-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C(C)C)(C(C)C)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 JRJMHISKSJUQLS-UHFFFAOYSA-N 0.000 description 1
- ZSQRXNYKHKDZHC-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-3,4-dimethylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)(C(C)C)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 ZSQRXNYKHKDZHC-UHFFFAOYSA-N 0.000 description 1
- OEJBGICQXZPYKN-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-3-ethyl-4-methylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C(C)C)(CC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 OEJBGICQXZPYKN-UHFFFAOYSA-N 0.000 description 1
- BSWAPLLPHMTDJB-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-3-ethylhexan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(CC)(CCC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 BSWAPLLPHMTDJB-UHFFFAOYSA-N 0.000 description 1
- CESWIDSGELLUFE-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-3-methylhexan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)(CCC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 CESWIDSGELLUFE-UHFFFAOYSA-N 0.000 description 1
- AMVMENJBVIKCEB-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-4-methylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C(C)C)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 AMVMENJBVIKCEB-UHFFFAOYSA-N 0.000 description 1
- APDQHTLFPNELDJ-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3,4-dimethylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C)(C(C)C)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 APDQHTLFPNELDJ-UHFFFAOYSA-N 0.000 description 1
- CVSHORNWWRJEPR-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3-ethyl-4-methylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C(C)C)(CC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 CVSHORNWWRJEPR-UHFFFAOYSA-N 0.000 description 1
- PCRZTLCKNOCRMZ-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3-ethylhexan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(CC)(CCC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 PCRZTLCKNOCRMZ-UHFFFAOYSA-N 0.000 description 1
- XDFASWDXPGKZNV-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3-methylhexan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C)(CCC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 XDFASWDXPGKZNV-UHFFFAOYSA-N 0.000 description 1
- OBFIXLJMCPBDQE-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3-propylhexan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(CCC)(CCC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 OBFIXLJMCPBDQE-UHFFFAOYSA-N 0.000 description 1
- ZXKFDTZODVDYED-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-4-methyl-3-propan-2-ylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C(C)C)(C(C)C)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZXKFDTZODVDYED-UHFFFAOYSA-N 0.000 description 1
- NOVMXOAQUKPIIW-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-4-methylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C(C)C)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 NOVMXOAQUKPIIW-UHFFFAOYSA-N 0.000 description 1
- VUDYQMOGQRVZHP-UHFFFAOYSA-N [3-bis(3,5-dimethylphenyl)phosphanyl-2,2-dimethyl-1,3-diphenylpropyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(P(C(C=2C=CC=CC=2)C(C)(C)C(P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)C=2C=CC=CC=2)C=2C=C(C)C=C(C)C=2)=C1 VUDYQMOGQRVZHP-UHFFFAOYSA-N 0.000 description 1
- QSKODNPGIWZAFX-UHFFFAOYSA-N [3-bis(4-methylphenyl)phosphanyl-2,2-dimethyl-1,3-diphenylpropyl]-bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C(C(C)(C)C(P(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 QSKODNPGIWZAFX-UHFFFAOYSA-N 0.000 description 1
- RVNVDLRZOHJDCB-UHFFFAOYSA-N [3-bis(4-methylphenyl)phosphanyl-2-methyl-1,3-diphenylpropyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 RVNVDLRZOHJDCB-UHFFFAOYSA-N 0.000 description 1
- AVXOESWKKURTML-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3,3-diethylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(CC)(CC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 AVXOESWKKURTML-UHFFFAOYSA-N 0.000 description 1
- JVSIHODQUUVXLH-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3,3-dimethylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)(C)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 JVSIHODQUUVXLH-UHFFFAOYSA-N 0.000 description 1
- ZZVWGSFRGNXCDV-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3-ethyl-3-methylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)(CC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 ZZVWGSFRGNXCDV-UHFFFAOYSA-N 0.000 description 1
- ZILHQDGTNMEODM-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3-ethylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(CC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 ZILHQDGTNMEODM-UHFFFAOYSA-N 0.000 description 1
- CRLCNFSEUMRFPB-UHFFFAOYSA-N [4-bis(4-methylphenyl)phosphanyl-3,3-diethylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(CC)(CC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 CRLCNFSEUMRFPB-UHFFFAOYSA-N 0.000 description 1
- NIMLQPWOYIZMGR-UHFFFAOYSA-N [4-bis(4-methylphenyl)phosphanyl-3-ethyl-3-methylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C)(CC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 NIMLQPWOYIZMGR-UHFFFAOYSA-N 0.000 description 1
- VCHDBLPQYJAQSQ-UHFFFAOYSA-N [5-(diphenylphosphanylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CC1OC(C)(C)OC1CP(C=1C=CC=CC=1)C1=CC=CC=C1 VCHDBLPQYJAQSQ-UHFFFAOYSA-N 0.000 description 1
- UVNZNIGDKACWAA-UHFFFAOYSA-N [Ru].C1CC=CCCC=C1 Chemical compound [Ru].C1CC=CCCC=C1 UVNZNIGDKACWAA-UHFFFAOYSA-N 0.000 description 1
- MWDNTFTWUNZWNS-UHFFFAOYSA-N [Ru].C1CCC=CC=CC1 Chemical compound [Ru].C1CCC=CC=CC1 MWDNTFTWUNZWNS-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- HVUARWKRVKZHHA-UHFFFAOYSA-N bis(3,5-dimethylphenyl) hydrogen phosphite Chemical compound CC1=CC(=CC(=C1)OP(O)OC2=CC(=CC(=C2)C)C)C HVUARWKRVKZHHA-UHFFFAOYSA-N 0.000 description 1
- QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical compound CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- JIXOCHSERUXVMW-UHFFFAOYSA-M chlororuthenium Chemical compound [Ru]Cl JIXOCHSERUXVMW-UHFFFAOYSA-M 0.000 description 1
- DBBUVLSRTWYISN-UHFFFAOYSA-N cycloheptane-1,2-diamine Chemical compound NC1CCCCCC1N DBBUVLSRTWYISN-UHFFFAOYSA-N 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical class NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- GTBPUYSGSDIIMM-UHFFFAOYSA-N phosphane;ruthenium Chemical compound P.[Ru] GTBPUYSGSDIIMM-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- PMKLSZDLLHGDMO-UHFFFAOYSA-L ruthenium(2+);triphenylphosphane;dichloride Chemical compound Cl[Ru]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 PMKLSZDLLHGDMO-UHFFFAOYSA-L 0.000 description 1
- PMMMCGISKBNZES-UHFFFAOYSA-K ruthenium(3+);tribromide;hydrate Chemical compound O.Br[Ru](Br)Br PMMMCGISKBNZES-UHFFFAOYSA-K 0.000 description 1
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 description 1
- 238000011924 stereoselective hydrogenation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- USLIQGJRXPCWLY-UHFFFAOYSA-K triiodoruthenium;hydrate Chemical compound O.I[Ru](I)I USLIQGJRXPCWLY-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002248058A JP3566955B2 (ja) | 2001-12-28 | 2002-08-28 | 新規ルテニウム錯体およびこれを触媒として用いるアルコール化合物の製造方法 |
| CA002414265A CA2414265A1 (en) | 2001-12-28 | 2002-12-16 | Novel ruthenium complexes and process for preparing alcoholic compounds using these |
| EP02028791A EP1323724B1 (en) | 2001-12-28 | 2002-12-23 | Ruthenium complexes and process for preparing alcoholic compounds using these |
| DE60218807T DE60218807T2 (de) | 2001-12-28 | 2002-12-23 | Rutheniumkomplexe und deren Verwendung zur Herstellung von Alkoholen |
| US10/330,501 US6790973B2 (en) | 2001-12-28 | 2002-12-27 | Ruthenium complexes and process for preparing alcoholic compounds using these |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001401170 | 2001-12-28 | ||
| JP2001-401170 | 2001-12-28 | ||
| JP2002248058A JP3566955B2 (ja) | 2001-12-28 | 2002-08-28 | 新規ルテニウム錯体およびこれを触媒として用いるアルコール化合物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003252884A JP2003252884A (ja) | 2003-09-10 |
| JP3566955B2 true JP3566955B2 (ja) | 2004-09-15 |
| JP2003252884A5 JP2003252884A5 (enExample) | 2004-12-16 |
Family
ID=26625402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002248058A Expired - Lifetime JP3566955B2 (ja) | 2001-12-28 | 2002-08-28 | 新規ルテニウム錯体およびこれを触媒として用いるアルコール化合物の製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6790973B2 (enExample) |
| EP (1) | EP1323724B1 (enExample) |
| JP (1) | JP3566955B2 (enExample) |
| CA (1) | CA2414265A1 (enExample) |
| DE (1) | DE60218807T2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2623509A1 (en) | 2012-02-01 | 2013-08-07 | Kanto Kagaku Kabushiki Kaisha | Method of producing an optically active amine compound by catalytic asymmetric hydrogenation using a ruthenium-diphosphine complex |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004101580A1 (ja) | 2003-05-19 | 2004-11-25 | Takeda Pharmaceutical Company Limited | ホスフィン-ボラン錯体の製造法 |
| GB0316439D0 (en) | 2003-07-15 | 2003-08-20 | Johnson Matthey Plc | Catalysts |
| DE602004030129D1 (de) * | 2003-07-31 | 2010-12-30 | Basf Se | Insektenfalle sowie verfahren zum fangen und aufbewahren von schadinsekten |
| ATE509024T1 (de) | 2003-08-13 | 2011-05-15 | Takasago Perfumery Co Ltd | Neuer übergangsmetallkomplex und verfahren zur herstellung von optisch aktivem alkohol mit dem komplex |
| JP5078608B2 (ja) | 2005-03-30 | 2012-11-21 | 関東化学株式会社 | 光学活性キヌクリジノール類の製造方法 |
| MX2009000616A (es) * | 2006-07-27 | 2009-01-28 | Hoffmann La Roche | Hidrogenacion asimetrica de 1,1,1-trifluoroacetona. |
| JP5172124B2 (ja) | 2006-09-29 | 2013-03-27 | 関東化学株式会社 | ２位に置換基を有する光学活性キヌクリジノール類の製造方法 |
| CN101541716B (zh) * | 2006-11-27 | 2012-10-03 | 弗门尼舍有限公司 | 通过钌/二齿配位体的络合物进行的酯的氢化 |
| CA2703671A1 (en) * | 2007-10-30 | 2009-05-07 | Kanata Chemical Technologies Inc. | Cationic transition metal catalysts |
| WO2009124897A1 (de) * | 2008-04-08 | 2009-10-15 | Basf Se | Komplexverbindung, enthaltend metallatom und phosphinderivat als ligand |
| JP5507931B2 (ja) * | 2009-09-01 | 2014-05-28 | 関東化学株式会社 | 芳香族複素環をもつ光学活性アルコールの製造方法 |
| DE102010002482B3 (de) | 2010-03-01 | 2012-01-05 | Technische Universität Braunschweig | Lumineszente Organometallverbindung |
| KR101808261B1 (ko) * | 2010-04-28 | 2017-12-12 | 다카사고 고료 고교 가부시키가이샤 | 루테늄 착체 및 광학적으로 활성인 알코올 화합물의 제조방법 |
| EP2578570A1 (en) * | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| JP6437187B2 (ja) * | 2013-07-26 | 2018-12-12 | 関東化學株式会社 | 光学活性２級アルコールの製造方法 |
| CN111320591B (zh) * | 2020-03-30 | 2023-03-31 | 陕西师范大学 | 一种合成手性γ-氨基醇的方法 |
| EP4516776A4 (en) * | 2022-04-26 | 2025-08-20 | Shenzhen Catalyst Tech Co Ltd | PROCESS FOR THE UNPROTECTED ASYMMETRIC PREPARATION OF NICOTINE |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2693190B1 (fr) * | 1992-07-02 | 1994-09-23 | Elf Aquitaine | Procédé d'hydrogénation énantiosélectif de la double liaison C=O OXO. |
| JP2731377B2 (ja) | 1994-12-07 | 1998-03-25 | 科学技術振興事業団 | 光学活性アルコール類の製造方法 |
| CA2164685C (en) | 1994-12-07 | 2005-03-08 | Takeshi Ohkuma | Method for producing an alcohol |
| JP4004123B2 (ja) | 1997-12-26 | 2007-11-07 | 独立行政法人科学技術振興機構 | ルテニウム錯体を触媒とするアルコール化合物の製造方法 |
| WO2001074829A1 (en) | 2000-03-30 | 2001-10-11 | Chirotech Technology Limited | Ruthenium-diphosphine complexes and their use as catalysts |
-
2002
- 2002-08-28 JP JP2002248058A patent/JP3566955B2/ja not_active Expired - Lifetime
- 2002-12-16 CA CA002414265A patent/CA2414265A1/en not_active Abandoned
- 2002-12-23 DE DE60218807T patent/DE60218807T2/de not_active Expired - Lifetime
- 2002-12-23 EP EP02028791A patent/EP1323724B1/en not_active Expired - Lifetime
- 2002-12-27 US US10/330,501 patent/US6790973B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2623509A1 (en) | 2012-02-01 | 2013-08-07 | Kanto Kagaku Kabushiki Kaisha | Method of producing an optically active amine compound by catalytic asymmetric hydrogenation using a ruthenium-diphosphine complex |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003252884A (ja) | 2003-09-10 |
| EP1323724A3 (en) | 2003-09-24 |
| EP1323724B1 (en) | 2007-03-14 |
| CA2414265A1 (en) | 2003-06-28 |
| US6790973B2 (en) | 2004-09-14 |
| DE60218807D1 (de) | 2007-04-26 |
| DE60218807T2 (de) | 2007-12-06 |
| US20030166978A1 (en) | 2003-09-04 |
| EP1323724A2 (en) | 2003-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3566955B2 (ja) | 新規ルテニウム錯体およびこれを触媒として用いるアルコール化合物の製造方法 | |
| JP4004123B2 (ja) | ルテニウム錯体を触媒とするアルコール化合物の製造方法 | |
| JP2736947B2 (ja) | 水溶性なスルホン酸アルカリ金属塩置換ビナフチルホスフイン遷移金属錯体及びこれを用いた不斉水素化法 | |
| CA2382779A1 (en) | Chiral ligands, transition-metal complexes thereof and uses thereof in asymmetric reactions | |
| CN101959898B (zh) | 具有(p-p)配位的二茂铁基双膦配体的钌配合物、制备它们的方法以及它们在均相催化中的用途 | |
| RU2352577C2 (ru) | Замещенные ферроценилдифосфины в качестве лигандов для гомогенных катализаторов гидрирования | |
| JP5454756B2 (ja) | ジホスフィン化合物、その遷移金属錯体およびその遷移金属錯体を含む触媒並びにホスフィンオキシド化合物及びジホスフィンオキシド化合物 | |
| JPH03255090A (ja) | ２，２’―ビス〔ジ―（３，５―ジアルキルフェニル）ホスフィノ〕―１，１’―ビナフチル及びこれを配位子とする遷移金属錯体 | |
| JP2000256384A (ja) | 新規な不斉配位子 | |
| CN103038242B (zh) | 具有(p-p)配位的二磷供体配位体的钌配合物及其制备方法 | |
| JPH0474192A (ja) | ２，２′―ビス（ジシクロペンチルホスフィノ）―１，１′―ビナフチル及びこれれを配位子とする遷移金属錯体 | |
| US5648548A (en) | Optically active asymmetric diphosphine and process for producing optically active substance in its presence | |
| JP4231274B2 (ja) | ホスフィン化合物、該化合物を配位子とする遷移金属錯体及び該錯体を含む不斉合成用触媒 | |
| JP4237979B2 (ja) | 光学活性フッ素化合物の製造方法 | |
| CN102781948A (zh) | 作为用于制备不对称合成的催化剂的配体的对映异构地富集的氨基二膦 | |
| JP4148702B2 (ja) | 新規なジホスフィン化合物、その製造中間体、該化合物を配位子とする遷移金属錯体並びに該錯体を含む不斉水素化触媒 | |
| JP5009613B2 (ja) | 不斉合成における使用のためのキラル配位子 | |
| JP4713134B2 (ja) | 光学活性アルキルフタリド類の製造方法 | |
| JPWO2002062809A1 (ja) | ルテニウム錯体及びアルコール化合物の製造方法 | |
| JP4519500B2 (ja) | 中性ロジウム−ホスフィン錯体の製造方法 | |
| JP4637876B2 (ja) | 光学活性アルコール化合物合成用触媒 | |
| JP2006063028A (ja) | 光学活性３−キヌクリジノール類の製造方法 | |
| JPH09294932A (ja) | ルテニウム−ホスフィン錯体 | |
| JP6261563B2 (ja) | 光学活性アルデヒドの製造方法 | |
| JP5011262B2 (ja) | ホスフィン化合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20040115 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20040115 |
|
| A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20040115 |
|
| TRDD | Decision of grant or rejection written | ||
| A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20040521 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20040601 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20040611 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 3566955 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080618 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090618 Year of fee payment: 5 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100618 Year of fee payment: 6 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110618 Year of fee payment: 7 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110618 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120618 Year of fee payment: 8 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120618 Year of fee payment: 8 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130618 Year of fee payment: 9 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |