ZA200507564B - Optically active copper catalyst composition - Google Patents
Optically active copper catalyst composition Download PDFInfo
- Publication number
- ZA200507564B ZA200507564B ZA200507564A ZA200507564A ZA200507564B ZA 200507564 B ZA200507564 B ZA 200507564B ZA 200507564 A ZA200507564 A ZA 200507564A ZA 200507564 A ZA200507564 A ZA 200507564A ZA 200507564 B ZA200507564 B ZA 200507564B
- Authority
- ZA
- South Africa
- Prior art keywords
- optically active
- copper
- compound
- isomer
- lewis acidity
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 56
- 239000010949 copper Substances 0.000 title claims description 43
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 42
- 229910052802 copper Inorganic materials 0.000 title claims description 42
- 239000003054 catalyst Substances 0.000 title claims description 39
- -1 lithium alkoxide Chemical class 0.000 claims description 65
- 150000001336 alkenes Chemical class 0.000 claims description 43
- 239000000243 solution Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- ORIHZIZPTZTNCU-UHFFFAOYSA-N 2-(hydroxyiminomethyl)phenol Chemical compound ON=CC1=CC=CC=C1O ORIHZIZPTZTNCU-UHFFFAOYSA-N 0.000 claims description 17
- 239000005749 Copper compound Substances 0.000 claims description 16
- 150000001880 copper compounds Chemical class 0.000 claims description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 16
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 150000002642 lithium compounds Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 239000002002 slurry Substances 0.000 claims description 7
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001639 boron compounds Chemical class 0.000 claims description 5
- 150000002363 hafnium compounds Chemical class 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 150000003609 titanium compounds Chemical class 0.000 claims description 5
- 150000003755 zirconium compounds Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 3
- POHPFVPVRKJHCR-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)alumane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[Al](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F POHPFVPVRKJHCR-UHFFFAOYSA-N 0.000 claims description 3
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 229910000085 borane Inorganic materials 0.000 claims description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 2
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- FQXBMHDSOQFCSX-UHFFFAOYSA-J oxolane;tetrachlorohafnium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Hf+4].C1CCOC1 FQXBMHDSOQFCSX-UHFFFAOYSA-J 0.000 claims description 2
- OJGXBHHMMHJMLS-UHFFFAOYSA-J oxolane;zirconium(4+);tetrachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Zr+4].C1CCOC1 OJGXBHHMMHJMLS-UHFFFAOYSA-J 0.000 claims description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 2
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 claims description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 2
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 4
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- 229910052719 titanium Inorganic materials 0.000 claims 2
- 239000010936 titanium Substances 0.000 claims 2
- 239000005750 Copper hydroxide Substances 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229940116318 copper carbonate Drugs 0.000 claims 1
- 229910001956 copper hydroxide Inorganic materials 0.000 claims 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 229960005335 propanol Drugs 0.000 description 34
- 229940108928 copper Drugs 0.000 description 27
- YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 26
- 230000003287 optical effect Effects 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 20
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 229940044613 1-propanol Drugs 0.000 description 17
- 150000004699 copper complex Chemical class 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 229950011148 cyclopropane Drugs 0.000 description 13
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 13
- VIMXTGUGWLAOFZ-UHFFFAOYSA-N ethyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=C(C)C)C1(C)C VIMXTGUGWLAOFZ-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 5
- 229940067157 phenylhydrazine Drugs 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical class C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- RXWOHFUULDINMC-UHFFFAOYSA-N 2-(3-nitrothiophen-2-yl)acetic acid Chemical compound OC(=O)CC=1SC=CC=1[N+]([O-])=O RXWOHFUULDINMC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QZIZJDFPLDQSPX-MRXNPFEDSA-N 2-[[(2R)-1-hydroxy-1,1-bis(2-methoxyphenyl)propan-2-yl]iminomethyl]-4-nitrophenol Chemical compound COC1=CC=CC=C1C(O)(C=1C(=CC=CC=1)OC)[C@@H](C)N=CC1=CC([N+]([O-])=O)=CC=C1O QZIZJDFPLDQSPX-MRXNPFEDSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 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 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 2
- PRTJSZPCEHPORP-SNAWJCMRSA-N (4e)-2-methylhexa-2,4-diene Chemical compound C\C=C\C=C(C)C PRTJSZPCEHPORP-SNAWJCMRSA-N 0.000 description 1
- PRTJSZPCEHPORP-UHFFFAOYSA-N (E)-2-methylhexa-2,4-diene Natural products CC=CC=C(C)C PRTJSZPCEHPORP-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BWIANEBBDZPLIU-UHFFFAOYSA-N 1,1-difluoro-4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C(F)F BWIANEBBDZPLIU-UHFFFAOYSA-N 0.000 description 1
- KOVZWJRALKLXOY-UHFFFAOYSA-N 1-(2-butoxy-5-tert-butylphenyl)propan-1-ol Chemical compound C(CCC)OC1=C(C=C(C=C1)C(C)(C)C)C(CC)O KOVZWJRALKLXOY-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- GFIJLOCTYRTZDT-UHFFFAOYSA-N 1-bromo-1-fluoro-4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C(F)Br GFIJLOCTYRTZDT-UHFFFAOYSA-N 0.000 description 1
- LHIPHZAUEPUWRF-UHFFFAOYSA-N 1-butoxy-2-diazonioethenolate Chemical compound CCCCOC(=O)C=[N+]=[N-] LHIPHZAUEPUWRF-UHFFFAOYSA-N 0.000 description 1
- OXSSRGFEKMFSQK-UHFFFAOYSA-N 1-chloro-2,5-dimethylhexa-2,4-diene Chemical compound CC(C)=CC=C(C)CCl OXSSRGFEKMFSQK-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 description 1
- HNHAOSJSGMRPJH-RRHRGVEJSA-N 2-[[(2R)-1,1-bis(2-butoxy-5-tert-butylphenyl)-1-hydroxy-3-phenylpropan-2-yl]iminomethyl]-4,6-dinitrophenol Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C=1C(=CC=C(C=1)C(C)(C)C)OCCCC)[C@H](N=CC=1C(=C(C=C(C=1)[N+]([O-])=O)[N+]([O-])=O)O)CC1=CC=CC=C1 HNHAOSJSGMRPJH-RRHRGVEJSA-N 0.000 description 1
- BHWLOOFJHWIMBO-VQJSHJPSSA-N 2-[[(2R)-1,1-bis(2-butoxy-5-tert-butylphenyl)-1-hydroxy-3-phenylpropan-2-yl]iminomethyl]-4-bromophenol Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C=1C(=CC=C(C=1)C(C)(C)C)OCCCC)[C@H](N=CC=1C(=CC=C(Br)C=1)O)CC1=CC=CC=C1 BHWLOOFJHWIMBO-VQJSHJPSSA-N 0.000 description 1
- BOLIYIDMKIWZPR-VQJSHJPSSA-N 2-[[(2R)-1,1-bis(2-butoxy-5-tert-butylphenyl)-1-hydroxy-3-phenylpropan-2-yl]iminomethyl]-4-chlorophenol Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C=1C(=CC=C(C=1)C(C)(C)C)OCCCC)[C@H](N=CC=1C(=CC=C(Cl)C=1)O)CC1=CC=CC=C1 BOLIYIDMKIWZPR-VQJSHJPSSA-N 0.000 description 1
- FTIDXQMXBVPPBZ-HUESYALOSA-N 2-[[(2R)-1,1-bis(2-butoxy-5-tert-butylphenyl)-1-hydroxy-3-phenylpropan-2-yl]iminomethyl]-4-methoxyphenol Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C=1C(=CC=C(C=1)C(C)(C)C)OCCCC)[C@H](N=CC=1C(=CC=C(OC)C=1)O)CC1=CC=CC=C1 FTIDXQMXBVPPBZ-HUESYALOSA-N 0.000 description 1
- IEGKBAWWCCRZNZ-RRHRGVEJSA-N 2-[[(2R)-1,1-bis(2-butoxy-5-tert-butylphenyl)-1-hydroxy-3-phenylpropan-2-yl]iminomethyl]-6-fluorophenol Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C=1C(=CC=C(C=1)C(C)(C)C)OCCCC)[C@H](N=CC=1C(=C(F)C=CC=1)O)CC1=CC=CC=C1 IEGKBAWWCCRZNZ-RRHRGVEJSA-N 0.000 description 1
- AULVRQCNPIFATB-VQJSHJPSSA-N 2-[[(2R)-1,1-bis(2-butoxy-5-tert-butylphenyl)-1-hydroxy-3-phenylpropan-2-yl]iminomethyl]-6-methoxyphenol Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C=1C(=CC=C(C=1)C(C)(C)C)OCCCC)[C@H](N=CC=1C(=C(OC)C=CC=1)O)CC1=CC=CC=C1 AULVRQCNPIFATB-VQJSHJPSSA-N 0.000 description 1
- CLXAPBKAVGJZMU-AREMUKBSSA-N 2-[[(2R)-1,1-bis(2-butoxy-5-tert-butylphenyl)-1-hydroxypropan-2-yl]iminomethyl]-4-chlorophenol Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C=1C(=CC=C(C=1)C(C)(C)C)OCCCC)[C@@H](C)N=CC1=CC(Cl)=CC=C1O CLXAPBKAVGJZMU-AREMUKBSSA-N 0.000 description 1
- UEWBYUYNJKSAME-AREMUKBSSA-N 2-[[(2R)-1,1-bis(2-butoxy-5-tert-butylphenyl)-1-hydroxypropan-2-yl]iminomethyl]-6-nitrophenol Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C=1C(=CC=C(C=1)C(C)(C)C)OCCCC)[C@@H](C)N=CC1=CC=CC([N+]([O-])=O)=C1O UEWBYUYNJKSAME-AREMUKBSSA-N 0.000 description 1
- OTGBYRGOTWONFU-QGZVFWFLSA-N 2-[[(2R)-1-hydroxy-1,1-bis(2-methoxyphenyl)propan-2-yl]iminomethyl]-6-methoxyphenol Chemical compound COC1=CC=CC(C=N[C@H](C)C(O)(C=2C(=CC=CC=2)OC)C=2C(=CC=CC=2)OC)=C1O OTGBYRGOTWONFU-QGZVFWFLSA-N 0.000 description 1
- LEFHXFNSXMDVDB-OAHLLOKOSA-N 2-[[(2R)-1-hydroxy-1,1-diphenylpropan-2-yl]iminomethyl]-4,6-dinitrophenol Chemical compound N([C@H](C)C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)=CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LEFHXFNSXMDVDB-OAHLLOKOSA-N 0.000 description 1
- TUJUHVXCTICXII-MRXNPFEDSA-N 2-[[(2R)-1-hydroxy-1,1-diphenylpropan-2-yl]iminomethyl]-4-nitrophenol Chemical compound N([C@H](C)C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)=CC1=CC([N+]([O-])=O)=CC=C1O TUJUHVXCTICXII-MRXNPFEDSA-N 0.000 description 1
- DZOULYFAEJFIDM-UHFFFAOYSA-N 2-amino-1,1-bis(2-butoxy-5-tert-butylphenyl)propan-1-ol Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C(C)N)C1=CC(C(C)(C)C)=CC=C1OCCCC DZOULYFAEJFIDM-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- OSUYLZXOVVTSDE-UHFFFAOYSA-N 2-diazonio-1-(2-methylpropoxy)ethenolate Chemical compound CC(C)COC([O-])=C[N+]#N OSUYLZXOVVTSDE-UHFFFAOYSA-N 0.000 description 1
- JBVSBLLOZVDAAZ-UHFFFAOYSA-N 2-diazonio-1-[(2-methylpropan-2-yl)oxy]ethenolate Chemical compound CC(C)(C)OC([O-])=C[N+]#N JBVSBLLOZVDAAZ-UHFFFAOYSA-N 0.000 description 1
- MIVRMHJOEYRXQB-UHFFFAOYSA-N 2-diazonio-1-methoxyethenolate Chemical compound COC(=O)C=[N+]=[N-] MIVRMHJOEYRXQB-UHFFFAOYSA-N 0.000 description 1
- FNXAUCKBTPCLJL-UHFFFAOYSA-N 2-diazonio-1-propan-2-yloxyethenolate Chemical compound CC(C)OC(=O)C=[N+]=[N-] FNXAUCKBTPCLJL-UHFFFAOYSA-N 0.000 description 1
- VNSOLURLIKWTEJ-OAHLLOKOSA-N 2-fluoro-6-[[(2R)-1-hydroxy-1,1-bis(2-methoxyphenyl)propan-2-yl]iminomethyl]-4-nitrophenol Chemical compound COC1=CC=CC=C1C(O)(C=1C(=CC=CC=1)OC)[C@@H](C)N=CC1=CC([N+]([O-])=O)=CC(F)=C1O VNSOLURLIKWTEJ-OAHLLOKOSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQGVOHURWDQPRE-HHHXNRCGSA-N 3-[[(2R)-1,1-bis(2-butoxy-5-tert-butylphenyl)-1-hydroxypropan-2-yl]iminomethyl]-4-hydroxybenzonitrile Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C=1C(=CC=C(C=1)C(C)(C)C)OCCCC)[C@@H](C)N=CC1=CC(C#N)=CC=C1O LQGVOHURWDQPRE-HHHXNRCGSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- WKEVRZCQFQDCIR-UHFFFAOYSA-N 4-chlorobut-1-ene Chemical compound ClCCC=C WKEVRZCQFQDCIR-UHFFFAOYSA-N 0.000 description 1
- RUYQASWHUGRQKA-QGZVFWFLSA-N 4-hydroxy-3-[[(2R)-1-hydroxy-1,1-bis(2-methoxyphenyl)propan-2-yl]iminomethyl]benzonitrile Chemical compound COC1=CC=CC=C1C(O)(C=1C(=CC=CC=1)OC)[C@@H](C)N=CC1=CC(C#N)=CC=C1O RUYQASWHUGRQKA-QGZVFWFLSA-N 0.000 description 1
- YLTBMRGKHJRGRW-UHFFFAOYSA-N 5-bromo-2,5-dimethylhex-2-ene Chemical compound CC(C)=CCC(C)(C)Br YLTBMRGKHJRGRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical compound OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical compound [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- YNYHGRUPNQLZHB-UHFFFAOYSA-M copper(1+);trifluoromethanesulfonate Chemical compound [Cu+].[O-]S(=O)(=O)C(F)(F)F YNYHGRUPNQLZHB-UHFFFAOYSA-M 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 1
- ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- AEJIMXVJZFYIHN-UHFFFAOYSA-N copper;dihydrate Chemical compound O.O.[Cu] AEJIMXVJZFYIHN-UHFFFAOYSA-N 0.000 description 1
- SDFNZYMSEOUVIF-UHFFFAOYSA-N copper;methanesulfonic acid Chemical compound [Cu].CS(O)(=O)=O SDFNZYMSEOUVIF-UHFFFAOYSA-N 0.000 description 1
- VNZQQAVATKSIBR-UHFFFAOYSA-L copper;octanoate Chemical compound [Cu+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O VNZQQAVATKSIBR-UHFFFAOYSA-L 0.000 description 1
- 239000011646 cupric carbonate Substances 0.000 description 1
- 235000019854 cupric carbonate Nutrition 0.000 description 1
- 238000005888 cyclopropanation reaction Methods 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- MXIRPJHGXWFUAE-UHFFFAOYSA-N lithium;propan-1-olate Chemical compound [Li+].CCC[O-] MXIRPJHGXWFUAE-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- BVHCLBKXHMUODU-UHFFFAOYSA-N methyl 2,2-dimethyl-3-(2,2,2-tribromoethyl)cyclopropane-1-carboxylate Chemical compound COC(=O)C1C(CC(Br)(Br)Br)C1(C)C BVHCLBKXHMUODU-UHFFFAOYSA-N 0.000 description 1
- YCUDCHKDRGFXPX-UHFFFAOYSA-N methyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropane-1-carboxylate Chemical compound COC(=O)C1C(CC(Cl)(Cl)Cl)C1(C)C YCUDCHKDRGFXPX-UHFFFAOYSA-N 0.000 description 1
- QFTQPFAIVFBZJO-UHFFFAOYSA-N methyl 2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1CC1(C)C QFTQPFAIVFBZJO-UHFFFAOYSA-N 0.000 description 1
- JWSLVXSFLAYZKU-UHFFFAOYSA-N methyl 2,5-dimethylhexa-2,4-dienoate Chemical compound COC(=O)C(C)=CC=C(C)C JWSLVXSFLAYZKU-UHFFFAOYSA-N 0.000 description 1
- KHHQNCNOFKTABM-UHFFFAOYSA-N methyl 2-methylcyclopropane-1-carboxylate Chemical compound COC(=O)C1CC1C KHHQNCNOFKTABM-UHFFFAOYSA-N 0.000 description 1
- YSILGROPIYCDQO-UHFFFAOYSA-N methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(Br)Br)C1(C)C YSILGROPIYCDQO-UHFFFAOYSA-N 0.000 description 1
- QJOOIMSFFIUFKX-UHFFFAOYSA-N methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(Cl)Cl)C1(C)C QJOOIMSFFIUFKX-UHFFFAOYSA-N 0.000 description 1
- HSDYMZWYGXHAQC-UHFFFAOYSA-N methyl 3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(F)F)C1(C)C HSDYMZWYGXHAQC-UHFFFAOYSA-N 0.000 description 1
- NQUXZZHNERUVNW-UHFFFAOYSA-N methyl 3-(2-bromo-2-fluoroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(F)Br)C1(C)C NQUXZZHNERUVNW-UHFFFAOYSA-N 0.000 description 1
- UDRYOVVIMGZJLW-UHFFFAOYSA-N methyl 3-(2-bromo-2-methylpropyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(CC(C)(C)Br)C1(C)C UDRYOVVIMGZJLW-UHFFFAOYSA-N 0.000 description 1
- ZVBZZNGAOAKDEJ-UHFFFAOYSA-N methyl 3-(2-chloroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(C)Cl)C1(C)C ZVBZZNGAOAKDEJ-UHFFFAOYSA-N 0.000 description 1
- OMJMSFSCPGDSQJ-UHFFFAOYSA-N methyl 3-(2-fluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(C)F)C1(C)C OMJMSFSCPGDSQJ-UHFFFAOYSA-N 0.000 description 1
- YYRMJZXCARUTDN-UHFFFAOYSA-N methyl 3-(3-methoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(C)C(=O)OC)C1(C)C YYRMJZXCARUTDN-UHFFFAOYSA-N 0.000 description 1
- VVELKALNWOEKAJ-VQJSHJPSSA-N methyl 3-[[(2R)-1,1-bis(2-butoxy-5-tert-butylphenyl)-1-hydroxy-3-phenylpropan-2-yl]iminomethyl]-2-hydroxybenzoate Chemical compound CCCCOC1=CC=C(C(C)(C)C)C=C1C(O)(C=1C(=CC=C(C=1)C(C)(C)C)OCCCC)[C@H](N=CC=1C(=C(C(=O)OC)C=CC=1)O)CC1=CC=CC=C1 VVELKALNWOEKAJ-VQJSHJPSSA-N 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YDNUIHHAHDMFJZ-UHFFFAOYSA-N tert-butyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC(C)=CC1C(C(=O)OC(C)(C)C)C1(C)C YDNUIHHAHDMFJZ-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- B01J31/0212—Alkoxylates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/38—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of titanium, zirconium or hafnium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
- B01J2231/325—Cyclopropanations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/0252—Salen ligands or analogues, e.g. derived from ethylenediamine and salicylaldehyde
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003093750 | 2003-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200507564B true ZA200507564B (en) | 2006-12-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200507564A ZA200507564B (en) | 2003-03-31 | 2004-03-25 | Optically active copper catalyst composition |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7253301B2 (de) |
| EP (1) | EP1607136B1 (de) |
| KR (1) | KR101113627B1 (de) |
| CN (1) | CN100398210C (de) |
| BR (1) | BRPI0408971A (de) |
| IL (1) | IL170728A (de) |
| PL (1) | PL1607136T3 (de) |
| RU (1) | RU2005133430A (de) |
| WO (1) | WO2004087317A1 (de) |
| ZA (1) | ZA200507564B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008133261A (ja) * | 2006-10-26 | 2008-06-12 | Sumitomo Chemical Co Ltd | 不斉銅錯体結晶の製造方法 |
| WO2008050661A1 (fr) * | 2006-10-26 | 2008-05-02 | Sumitomo Chemical Company, Limited | Procédé servant à produire un cristal de complexe asymétrique du cuivre |
| US8680328B2 (en) * | 2008-09-10 | 2014-03-25 | Sumitomo Chemical Company, Limited | Method for producing optically active cyclopropane carboxylic acid ester compound, asymmetric copper complex, and optically active salicylideneaminoalcohol compound |
| CN102533923A (zh) * | 2011-12-19 | 2012-07-04 | 浙江工业大学 | 有机溶剂共溶剂生物拆分制备(s)-(+)-2,2-二甲基环丙烷甲酸的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59225194A (ja) * | 1983-06-03 | 1984-12-18 | Sumitomo Chem Co Ltd | 新規不斉銅錯体ならびに同錯体を触媒とするシクロプロパンカルボン酸エステルの不斉合成法 |
| DE69906607T2 (de) * | 1998-01-29 | 2003-12-18 | Sumitomo Chemical Co., Ltd. | Verfahren zur Herstellung von optisch aktiven Chrysanthemumsäure |
| KR20010074548A (ko) | 2000-01-25 | 2001-08-04 | 고사이 아끼오 | 키랄 구리 착물 촉매 조성물 및 그를 이용한 비대칭 제조방법 |
| JP4742423B2 (ja) | 2000-01-25 | 2011-08-10 | 住友化学株式会社 | 不斉銅錯体の製造法およびそれを用いる光学活性シクロプロパン化合物の製造法 |
| JP2003012675A (ja) * | 2001-04-27 | 2003-01-15 | Sumitomo Chem Co Ltd | 不斉銅錯体、その製造方法および不斉銅錯体を用いる光学活性シクロプロパン化合物の製造方法 |
| ES2354685T3 (es) | 2001-04-27 | 2011-03-17 | Sumitomo Chemical Company, Limited | Complejo de cobre asimétrico y reacción de ciclopropano que utiliza el mismo. |
-
2004
- 2004-03-25 KR KR1020057018701A patent/KR101113627B1/ko not_active IP Right Cessation
- 2004-03-25 EP EP04723350A patent/EP1607136B1/de not_active Expired - Lifetime
- 2004-03-25 ZA ZA200507564A patent/ZA200507564B/en unknown
- 2004-03-25 BR BRPI0408971-5A patent/BRPI0408971A/pt not_active Application Discontinuation
- 2004-03-25 PL PL04723350T patent/PL1607136T3/pl unknown
- 2004-03-25 US US10/549,939 patent/US7253301B2/en not_active Expired - Fee Related
- 2004-03-25 WO PCT/JP2004/004185 patent/WO2004087317A1/ja active Application Filing
- 2004-03-25 CN CNB2004800148249A patent/CN100398210C/zh not_active Expired - Fee Related
- 2004-03-25 RU RU2005133430/04A patent/RU2005133430A/ru not_active Application Discontinuation
-
2005
- 2005-09-07 IL IL170728A patent/IL170728A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1607136B1 (de) | 2012-05-23 |
| WO2004087317A1 (ja) | 2004-10-14 |
| KR101113627B1 (ko) | 2012-02-13 |
| EP1607136A4 (de) | 2007-07-04 |
| BRPI0408971A (pt) | 2006-04-04 |
| EP1607136A1 (de) | 2005-12-21 |
| US20060211879A1 (en) | 2006-09-21 |
| RU2005133430A (ru) | 2006-04-20 |
| US7253301B2 (en) | 2007-08-07 |
| PL1607136T3 (pl) | 2012-09-28 |
| CN1798609A (zh) | 2006-07-05 |
| IL170728A (en) | 2009-12-24 |
| CN100398210C (zh) | 2008-07-02 |
| KR20050121707A (ko) | 2005-12-27 |
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