JP2004524315A - ピラゾリルピリミジン - Google Patents

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Publication number

JP2004524315A

JP2004524315A JP2002567926A JP2002567926A JP2004524315A JP 2004524315 A JP2004524315 A JP 2004524315A JP 2002567926 A JP2002567926 A JP 2002567926A JP 2002567926 A JP2002567926 A JP 2002567926A JP 2004524315 A JP2004524315 A JP 2004524315A

Authority

JP

Japan

Prior art keywords

alkyl

group

chlorine

optionally

halogenoalkyl

Prior art date

2001-02-22

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.)

Pending

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• BWIHJLOBZMKPKS-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)pyrimidine Chemical compound N1C=CC(C=2N=CC=CN=2)=N1 BWIHJLOBZMKPKS-UHFFFAOYSA-N 0.000 title claims abstract description 34
• 238000000034 method Methods 0.000 claims abstract description 46
• 239000000575 pesticide Substances 0.000 claims abstract description 7
• -1 cyano, hydroxyl Chemical group 0.000 claims description 213
• 150000001875 compounds Chemical group 0.000 claims description 189
• 239000000460 chlorine Substances 0.000 claims description 134
• 229910052801 chlorine Inorganic materials 0.000 claims description 132
• 239000011737 fluorine Substances 0.000 claims description 121
• 229910052731 fluorine Inorganic materials 0.000 claims description 121
• 239000001257 hydrogen Substances 0.000 claims description 102
• 229910052739 hydrogen Inorganic materials 0.000 claims description 102
• 125000000217 alkyl group Chemical group 0.000 claims description 99
• 150000002431 hydrogen Chemical class 0.000 claims description 85
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 75
• 125000001246 bromo group Chemical group Br* 0.000 claims description 69
• 125000001424 substituent group Chemical group 0.000 claims description 68
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 64
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 61
• 229910052736 halogen Inorganic materials 0.000 claims description 59
• 150000002367 halogens Chemical class 0.000 claims description 59
• 229910052760 oxygen Inorganic materials 0.000 claims description 59
• 239000001301 oxygen Substances 0.000 claims description 57
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 56
• 229910052794 bromium Inorganic materials 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 54
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 53
• 125000005842 heteroatom Chemical group 0.000 claims description 53
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 50
• 125000000623 heterocyclic group Chemical group 0.000 claims description 47
• 239000003085 diluting agent Substances 0.000 claims description 46
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 229910052717 sulfur Inorganic materials 0.000 claims description 46
• 229920006395 saturated elastomer Polymers 0.000 claims description 43
• 125000001188 haloalkyl group Chemical group 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
• UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 37
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 37
• 239000011593 sulfur Substances 0.000 claims description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 36
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 35
• 125000004434 sulfur atom Chemical group 0.000 claims description 32
• 239000003054 catalyst Substances 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 28
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 27
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 24
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 24
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
• 239000002585 base Substances 0.000 claims description 21
• 239000011230 binding agent Substances 0.000 claims description 21
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 18
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
• 150000002825 nitriles Chemical class 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• 241000607479 Yersinia pestis Species 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 12
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 11
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 10
• 230000008569 process Effects 0.000 claims description 10
• 239000011734 sodium Substances 0.000 claims description 10
• 229920002554 vinyl polymer Polymers 0.000 claims description 10
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 9
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
• 150000001540 azides Chemical class 0.000 claims description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 150000002500 ions Chemical class 0.000 claims description 8
• 230000003278 mimic effect Effects 0.000 claims description 8
• 150000002902 organometallic compounds Chemical class 0.000 claims description 8
• 125000003355 oxamoyl group Chemical group C(C(=O)N)(=O)* 0.000 claims description 8
• 239000007800 oxidant agent Substances 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 239000011575 calcium Substances 0.000 claims description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
• BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 6
• JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical group [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 6
• NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 6
• FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 6
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
• 125000004104 aryloxy group Chemical group 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
• 239000011630 iodine Substances 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 239000011777 magnesium Substances 0.000 claims description 6
• 229940096405 magnesium cation Drugs 0.000 claims description 6
• FOEMIZSFFWGXHX-UHFFFAOYSA-N 2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC=N1 FOEMIZSFFWGXHX-UHFFFAOYSA-N 0.000 claims description 5
• 125000004450 alkenylene group Chemical group 0.000 claims description 5
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 238000002156 mixing Methods 0.000 claims description 5
• OIGXNHYFKZCTCH-UHFFFAOYSA-N 2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC=CC=N1 OIGXNHYFKZCTCH-UHFFFAOYSA-N 0.000 claims description 4
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
• ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 4
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
• ZAHXYMFVNNUHCP-UHFFFAOYSA-N Naphazoline nitrate Chemical group O[N+]([O-])=O.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 ZAHXYMFVNNUHCP-UHFFFAOYSA-N 0.000 claims description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• 125000001118 alkylidene group Chemical group 0.000 claims description 4
• 239000001099 ammonium carbonate Substances 0.000 claims description 4
• 235000012501 ammonium carbonate Nutrition 0.000 claims description 4
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 4
• 125000005412 pyrazyl group Chemical group 0.000 claims description 4
• 125000005495 pyridazyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 150000003573 thiols Chemical class 0.000 claims description 4
• 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims description 4
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
• ILFIRBGRMCGNOO-UHFFFAOYSA-N 1,1-bis($l^{1}-oxidanyl)ethene Chemical group [O]C([O])=C ILFIRBGRMCGNOO-UHFFFAOYSA-N 0.000 claims description 3
• 229930194542 Keto Natural products 0.000 claims description 3
• 230000009471 action Effects 0.000 claims description 3
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 239000004094 surface-active agent Substances 0.000 claims description 3
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
• HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical group [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 2
• 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
• 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 claims description 2
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
• 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
• 125000006038 hexenyl group Chemical group 0.000 claims description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
• 229940006487 lithium cation Drugs 0.000 claims description 2
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 230000001590 oxidative effect Effects 0.000 claims description 2
• 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
• 125000004306 triazinyl group Chemical group 0.000 claims description 2
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
• 235000019000 fluorine Nutrition 0.000 claims 59
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 58
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 53
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
• 229910052799 carbon Inorganic materials 0.000 claims 5
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
• 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims 2
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 2
• 239000004067 bulking agent Substances 0.000 claims 2
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
• 125000005702 oxyalkylene group Chemical group 0.000 claims 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
• 239000000126 substance Substances 0.000 abstract description 27
• 229910052727 yttrium Inorganic materials 0.000 abstract description 2
• 241000196324 Embryophyta Species 0.000 description 59
• 239000000203 mixture Substances 0.000 description 50
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
• 239000007858 starting material Substances 0.000 description 39
• 239000002904 solvent Substances 0.000 description 37
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
• 239000003995 emulsifying agent Substances 0.000 description 26
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
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