JP5178052B2 - 光学活性パーフルオロアルキル基含有化合物の製造方法 - Google Patents
光学活性パーフルオロアルキル基含有化合物の製造方法 Download PDFInfo
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- JP5178052B2 JP5178052B2 JP2007144334A JP2007144334A JP5178052B2 JP 5178052 B2 JP5178052 B2 JP 5178052B2 JP 2007144334 A JP2007144334 A JP 2007144334A JP 2007144334 A JP2007144334 A JP 2007144334A JP 5178052 B2 JP5178052 B2 JP 5178052B2
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- Prior art keywords
- aldehyde
- group
- acetyl
- general formula
- ethane
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- 150000001875 compounds Chemical class 0.000 title claims description 25
- 125000005010 perfluoroalkyl group Chemical group 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 9
- -1 methylethynyl group Chemical group 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 230000003287 optical effect Effects 0.000 claims description 26
- MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
- 239000003444 phase transfer catalyst Substances 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 claims description 3
- GXAFHGICPVJCCZ-UHFFFAOYSA-M trimethyl(octadecyl)azanium;fluoride Chemical compound [F-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C GXAFHGICPVJCCZ-UHFFFAOYSA-M 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 229910052757 nitrogen Inorganic materials 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 35
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 30
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 21
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 20
- 239000012046 mixed solvent Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- MGGPNTBEWITGIJ-GFCCVEGCSA-N (2R)-1,1,1-trifluoro-2-naphthalen-2-ylpropan-2-ol Chemical compound C1=CC=CC2=CC([C@](O)(C)C(F)(F)F)=CC=C21 MGGPNTBEWITGIJ-GFCCVEGCSA-N 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 5
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 4
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 4
- 238000006692 trifluoromethylation reaction Methods 0.000 description 4
- RLRMXTVZEDMFHB-SECBINFHSA-N (1R)-1-(trifluoromethyl)-2,3-dihydroinden-1-ol Chemical compound C1=CC=C2[C@@](O)(C(F)(F)F)CCC2=C1 RLRMXTVZEDMFHB-SECBINFHSA-N 0.000 description 3
- BDTPMXRVQUXISY-SNVBAGLBSA-N (1R)-1-(trifluoromethyl)-3,4-dihydro-2H-naphthalen-1-ol Chemical compound C1=CC=C2[C@@](O)(C(F)(F)F)CCCC2=C1 BDTPMXRVQUXISY-SNVBAGLBSA-N 0.000 description 3
- VLURUZGLTUQTDD-MRVPVSSYSA-N (2R)-1,1,1-trifluoro-2-(3-nitrophenyl)propan-2-ol Chemical compound FC(F)(F)[C@@](O)(C)C1=CC=CC([N+]([O-])=O)=C1 VLURUZGLTUQTDD-MRVPVSSYSA-N 0.000 description 3
- LCRHNHSPQULWRG-SECBINFHSA-N (2R)-1,1,1-trifluoro-2-(4-methoxyphenyl)propan-2-ol Chemical compound COC1=CC=C([C@@](C)(O)C(F)(F)F)C=C1 LCRHNHSPQULWRG-SECBINFHSA-N 0.000 description 3
- VUESJESTGDDESM-MRVPVSSYSA-N (2R)-1,1,1-trifluoro-2-(4-nitrophenyl)propan-2-ol Chemical compound FC(F)(F)[C@@](O)(C)C1=CC=C([N+]([O-])=O)C=C1 VUESJESTGDDESM-MRVPVSSYSA-N 0.000 description 3
- NSFHTONABRSTTQ-MRVPVSSYSA-N (2R)-2-(3-bromophenyl)-1,1,1-trifluoropropan-2-ol Chemical compound FC(F)(F)[C@@](O)(C)C1=CC=CC(Br)=C1 NSFHTONABRSTTQ-MRVPVSSYSA-N 0.000 description 3
- JDCUESCJSUEXRL-MRVPVSSYSA-N (2R)-2-(3-chlorophenyl)-1,1,1-trifluoropropan-2-ol Chemical compound FC(F)(F)[C@@](O)(C)C1=CC=CC(Cl)=C1 JDCUESCJSUEXRL-MRVPVSSYSA-N 0.000 description 3
- VXBWCPWBCRCUAU-MRVPVSSYSA-N (2R)-2-(4-chlorophenyl)-1,1,1-trifluoropropan-2-ol Chemical compound FC(F)(F)[C@@](O)(C)C1=CC=C(Cl)C=C1 VXBWCPWBCRCUAU-MRVPVSSYSA-N 0.000 description 3
- DQMMTAXIJXTESZ-SECBINFHSA-N (2r)-1,1,1-trifluoro-2-phenylbutan-2-ol Chemical compound CC[C@](O)(C(F)(F)F)C1=CC=CC=C1 DQMMTAXIJXTESZ-SECBINFHSA-N 0.000 description 3
- ZWLWJQBJGOXGMA-MRVPVSSYSA-N (2r)-2-(4-bromophenyl)-1,1,1-trifluoropropan-2-ol Chemical compound FC(F)(F)[C@@](O)(C)C1=CC=C(Br)C=C1 ZWLWJQBJGOXGMA-MRVPVSSYSA-N 0.000 description 3
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFIWQJOGTQJXQZ-UHFFFAOYSA-N C1=CC2=C(C(=C1)I)C(=C(C=C2)C=O)I Chemical compound C1=CC2=C(C(=C1)I)C(=C(C=C2)C=O)I LFIWQJOGTQJXQZ-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- KQQKDNLMXYUGGE-LLVKDONJSA-N (1R)-6-methoxy-1-(trifluoromethyl)-3,4-dihydro-2H-naphthalen-1-ol Chemical compound COc1ccc2c(CCC[C@]2(O)C(F)(F)F)c1 KQQKDNLMXYUGGE-LLVKDONJSA-N 0.000 description 2
- CYINUNLEKOSYDH-CYBMUJFWSA-N (2R)-1,1,1-trifluoro-2-(6-methoxynaphthalen-2-yl)propan-2-ol Chemical compound COc1ccc2cc(ccc2c1)[C@@](C)(O)C(F)(F)F CYINUNLEKOSYDH-CYBMUJFWSA-N 0.000 description 2
- STKVXXIJOMEBED-SNVBAGLBSA-N (2R)-1,1,1-trifluoro-2-phenylpentan-2-ol Chemical compound CCC[C@@](O)(c1ccccc1)C(F)(F)F STKVXXIJOMEBED-SNVBAGLBSA-N 0.000 description 2
- MGGPNTBEWITGIJ-LBPRGKRZSA-N (2S)-1,1,1-trifluoro-2-naphthalen-2-ylpropan-2-ol Chemical compound C1=CC=CC2=CC([C@@](O)(C)C(F)(F)F)=CC=C21 MGGPNTBEWITGIJ-LBPRGKRZSA-N 0.000 description 2
- JYDIJFKNXHPWBJ-FBBRVDCYSA-M (s)-[(2r,4s,5r)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;chloride Chemical compound [Cl-].C([C@H]([C@H](C1)C=C)C[C@@H]2[C@@H](O)C3=CC=NC4=CC=C(C=C43)OC)C[N+]21CC1=CC=CC=C1 JYDIJFKNXHPWBJ-FBBRVDCYSA-M 0.000 description 2
- FTCTTWRIOHDFIL-UHFFFAOYSA-N 1,3-difluoronaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(F)=C(C=O)C(F)=CC2=C1 FTCTTWRIOHDFIL-UHFFFAOYSA-N 0.000 description 2
- PMASCIUOTILTKS-UHFFFAOYSA-N 1,6-dibromonaphthalene-2-carbaldehyde Chemical compound BrC1=C(C=O)C=CC2=CC(Br)=CC=C21 PMASCIUOTILTKS-UHFFFAOYSA-N 0.000 description 2
- CJRZUMXKEVGGGG-UHFFFAOYSA-N 1-(2,3-dipropoxyphenyl)ethanone Chemical compound CCCOC1=CC=CC(C(C)=O)=C1OCCC CJRZUMXKEVGGGG-UHFFFAOYSA-N 0.000 description 2
- LVZUKZRFSBXVDC-UHFFFAOYSA-N 1-(2,4,6-tripropoxyphenyl)ethanone Chemical compound CCCOc1cc(OCCC)c(C(C)=O)c(OCCC)c1 LVZUKZRFSBXVDC-UHFFFAOYSA-N 0.000 description 2
- FACJMWCGGNKOGF-UHFFFAOYSA-N 1-(2,6-dipropoxyphenyl)ethanone Chemical compound CCCOC1=CC=CC(OCCC)=C1C(C)=O FACJMWCGGNKOGF-UHFFFAOYSA-N 0.000 description 2
- DWPLEOPKBWNPQV-UHFFFAOYSA-N 1-(2-methoxyphenyl)ethanone Chemical compound COC1=CC=CC=C1C(C)=O DWPLEOPKBWNPQV-UHFFFAOYSA-N 0.000 description 2
- BOKCYXGTJYZHBA-UHFFFAOYSA-N 1-(2-propoxyphenyl)ethanone Chemical compound CCCOC1=CC=CC=C1C(C)=O BOKCYXGTJYZHBA-UHFFFAOYSA-N 0.000 description 2
- IBSDEQJERNHTCP-UHFFFAOYSA-N 1-(2-propylphenyl)ethanone Chemical compound CCCC1=CC=CC=C1C(C)=O IBSDEQJERNHTCP-UHFFFAOYSA-N 0.000 description 2
- LAICVBVJFJJUSG-UHFFFAOYSA-N 1-(3,5-dipropoxyphenyl)ethanone Chemical compound CCCOC1=CC(OCCC)=CC(C(C)=O)=C1 LAICVBVJFJJUSG-UHFFFAOYSA-N 0.000 description 2
- JYAQYXOVOHJRCS-UHFFFAOYSA-N 1-(3-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Br)=C1 JYAQYXOVOHJRCS-UHFFFAOYSA-N 0.000 description 2
- UUWJBXKHMMQDED-UHFFFAOYSA-N 1-(3-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Cl)=C1 UUWJBXKHMMQDED-UHFFFAOYSA-N 0.000 description 2
- ARKIFHPFTHVKDT-UHFFFAOYSA-N 1-(3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=CC([N+]([O-])=O)=C1 ARKIFHPFTHVKDT-UHFFFAOYSA-N 0.000 description 2
- NJVMQLXTCKOYLY-UHFFFAOYSA-N 1-(3-propoxyphenyl)ethanone Chemical compound CCCOC1=CC=CC(C(C)=O)=C1 NJVMQLXTCKOYLY-UHFFFAOYSA-N 0.000 description 2
- MCAGLIMVIIWSOJ-UHFFFAOYSA-N 1-(3-propylnaphthalen-2-yl)ethanone Chemical compound C1=CC=C2C=C(C(C)=O)C(CCC)=CC2=C1 MCAGLIMVIIWSOJ-UHFFFAOYSA-N 0.000 description 2
- UQWHVBJAAMMMPO-UHFFFAOYSA-N 1-(3-propylphenyl)ethanone Chemical compound CCCC1=CC=CC(C(C)=O)=C1 UQWHVBJAAMMMPO-UHFFFAOYSA-N 0.000 description 2
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 2
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 2
- RTYYKCQJSTZADZ-UHFFFAOYSA-N 1-(4-propoxyphenyl)ethanone Chemical compound CCCOC1=CC=C(C(C)=O)C=C1 RTYYKCQJSTZADZ-UHFFFAOYSA-N 0.000 description 2
- ZNBVIYMIVFKTIW-UHFFFAOYSA-N 1-(4-propylphenyl)ethanone Chemical compound CCCC1=CC=C(C(C)=O)C=C1 ZNBVIYMIVFKTIW-UHFFFAOYSA-N 0.000 description 2
- GGWCZBGAIGGTDA-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)ethanone Chemical compound C1=C(C(C)=O)C=CC2=CC(OC)=CC=C21 GGWCZBGAIGGTDA-UHFFFAOYSA-N 0.000 description 2
- DUKJZYZDOKKAMU-UHFFFAOYSA-N 1-chloronaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(Cl)=C(C=O)C=CC2=C1 DUKJZYZDOKKAMU-UHFFFAOYSA-N 0.000 description 2
- MWWABFPMKIGOHV-UHFFFAOYSA-N 1-decoxynaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(OCCCCCCCCCC)=C(C=O)C=CC2=C1 MWWABFPMKIGOHV-UHFFFAOYSA-N 0.000 description 2
- YPWUQMKWNNQMDX-UHFFFAOYSA-N 1-fluoronaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(F)=C(C=O)C=CC2=C1 YPWUQMKWNNQMDX-UHFFFAOYSA-N 0.000 description 2
- KNLSMHJKAJZBQK-UHFFFAOYSA-N 1-iodonaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(I)=C(C=O)C=CC2=C1 KNLSMHJKAJZBQK-UHFFFAOYSA-N 0.000 description 2
- XQIMHJNMEFIADP-UHFFFAOYSA-N 1-nitronaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C([N+](=O)[O-])=C(C=O)C=CC2=C1 XQIMHJNMEFIADP-UHFFFAOYSA-N 0.000 description 2
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
- JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 2
- IGBKOBRBFKNYNC-UHFFFAOYSA-N 2,3-dipropylbenzaldehyde Chemical compound CCCC1=CC=CC(C=O)=C1CCC IGBKOBRBFKNYNC-UHFFFAOYSA-N 0.000 description 2
- CRBZVDLXAIFERF-UHFFFAOYSA-N 2,4,6-trimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(C=O)C(OC)=C1 CRBZVDLXAIFERF-UHFFFAOYSA-N 0.000 description 2
- HIKRJHFHGKZKRI-UHFFFAOYSA-N 2,4,6-trimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(C)=C1 HIKRJHFHGKZKRI-UHFFFAOYSA-N 0.000 description 2
- ZKEZHPWKUOFRIB-UHFFFAOYSA-N 2,4,6-tripropoxybenzaldehyde Chemical compound CCCOC1=CC(OCCC)=C(C=O)C(OCCC)=C1 ZKEZHPWKUOFRIB-UHFFFAOYSA-N 0.000 description 2
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
- MVOWILXGBBQBMR-UHFFFAOYSA-N 2,4-dipropoxybenzaldehyde Chemical compound CCCOC1=CC=C(C=O)C(OCCC)=C1 MVOWILXGBBQBMR-UHFFFAOYSA-N 0.000 description 2
- XALXSURAKNLXSX-UHFFFAOYSA-N 2,4-dipropylbenzaldehyde Chemical compound CCCC1=CC=C(C=O)C(CCC)=C1 XALXSURAKNLXSX-UHFFFAOYSA-N 0.000 description 2
- NADIKWZQGLHOLY-UHFFFAOYSA-N 2,5-dipropoxybenzaldehyde Chemical compound CCCOC1=CC=C(OCCC)C(C=O)=C1 NADIKWZQGLHOLY-UHFFFAOYSA-N 0.000 description 2
- VYQAFPABNHKGAP-UHFFFAOYSA-N 2,6-dipropoxybenzaldehyde Chemical compound CCCOC1=CC=CC(OCCC)=C1C=O VYQAFPABNHKGAP-UHFFFAOYSA-N 0.000 description 2
- VJEWYOFZCKQFRH-UHFFFAOYSA-N 2,6-dipropylbenzaldehyde Chemical compound CCCC1=CC=CC(CCC)=C1C=O VJEWYOFZCKQFRH-UHFFFAOYSA-N 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- WWKKTHALZAYYAI-UHFFFAOYSA-N 2-iodobenzaldehyde Chemical compound IC1=CC=CC=C1C=O WWKKTHALZAYYAI-UHFFFAOYSA-N 0.000 description 2
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- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 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
- 150000001649 bromium compounds Chemical class 0.000 description 1
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- 230000018044 dehydration Effects 0.000 description 1
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- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
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- 238000009776 industrial production Methods 0.000 description 1
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- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
- YNMZZHPSYMOGCI-UHFFFAOYSA-N undecan-3-one Chemical compound CCCCCCCCC(=O)CC YNMZZHPSYMOGCI-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
K.Iseki,et.al.,Tetrahedron Letters,1994,Vol.35,No.19,3137−3138。 S.Caron,et.al.,Synthesis,2003,No.11,1693−1698。 H.Nagao,et.al.,Chemistry Letters,Vol.36,No.5,666−667(2007)。
又は一般式(3)
を示し、R1とR2は同じ基であることはない。またR1とR2は縮環し炭素数4〜8の環状構造をとっても良い。]
で表されるカルボニル基含有化合物を、一般式(7)
、化学式(8)
で表されるアンモニウム塩存在下、一般式(5)
で表される光学活性パーフルオロアルキル基含有化合物の製造方法。
3,4,5−トリヨードナフト−2−アルデヒド、3,4,6−トリヨードナフト−2−アルデヒド、3,4,7−トリヨードナフト−2−アルデヒド、3,4,8−トリヨードナフト−2−アルデヒド、3,5,6−トリヨードナフト−2−アルデヒド、3,5,7−トリヨードナフト−2−アルデヒド、3,5,8−トリヨードナフト−2−アルデヒド、3,6,7−トリヨードナフト−2−アルデヒド、3,6,8−トリヨードナフト−2−アルデヒド、3,7,8−トリヨードナフト−2−アルデヒド、4,5,6−トリヨードナフト−2−アルデヒド、4,5,7−トリヨードナフト−2−アルデヒド、4,5,8−トリヨードナフト−2−アルデヒド、4,6,7−トリヨードナフト−2−アルデヒド、4,6,8−トリヨードナフト−2−アルデヒド、4,7,8−トリヨードナフト−2−アルデヒド、5,6,7−トリヨードナフト−2−アルデヒド、5,6,8−トリヨードナフト−2−アルデヒド、5,7,8−トリヨードナフト−2−アルデヒド、6,7,8−トリヨードナフト−2−アルデヒド等が例示される。
2−アセチル−1−n−オクチルナフタレン、2−アセチル−3−n−オクチルナフタレン、2−アセチル−4−n−オクチルナフタレン、2−アセチル−5−n−オクチルナフタレン、2−アセチル−6−n−オクチルナフタレン、2−アセチル−7−n−オクチルナフタレン、2−アセチル−8−n−オクチルナフタレン、2−アセチル−1−n−ノニルナフタレン、2−アセチル−3−n−ノニルナフタレン、2−アセチル−4−n−ノニルナフタレン、2−アセチル−5−n−ノニルナフタレン、2−アセチル−6−n−ノニルナフタレン、2−アセチル−7−n−ノニルナフタレン、2−アセチル−8−n−ノニルナフタレン、
2−アセチル−1−n−デシルナフタレン、2−アセチル−3−n−デシルナフタレン、2−アセチル−4−n−デシルナフタレン、2−アセチル−5−n−デシルナフタレン、2−アセチル−6−n−デシルナフタレン、2−アセチル−7−n−デシルナフタレン、2−アセチル−8−n−デシルナフタレン等が例示される。
1−ブロモナフト−2−アルデヒド、3−ブロモナフト−2−アルデヒド、4−ブロモナフト−2−アルデヒド、5−ブロモナフト−2−アルデヒド、6−ブロモナフト−2−アルデヒド、7−ブロモナフト−2−アルデヒド、8−ブロモナフト−2−アルデヒド、1,3−ジブロモナフト−2−アルデヒド、1,4−ジブロモナフト−2−アルデヒド、1,5−ジブロモナフト−2−アルデヒド、1,6−ジブロモナフト−2−アルデヒド、1,7−ジブロモナフト−2−アルデヒド、1,8−ジブロモナフト−2−アルデヒド、3,4−ジブロモナフト−2−アルデヒド、3,5−ジブロモナフト−2−アルデヒド、3,6−ジブロモナフト−2−アルデヒド、3,7−ジブロモナフト−2−アルデヒド、3,8−ジブロモナフト−2−アルデヒド、4,5−ジブロモナフト−2−アルデヒド、4,6−ジブロモナフト−2−アルデヒド、4,7−ジブロモナフト−2−アルデヒド、4,8−ジブロモナフト−2−アルデヒド、5,6−ジブロモナフト−2−アルデヒド、5,7−ジブロモナフト−2−アルデヒド、5,8−ジブロモナフト−2−アルデヒド、6,7−ジブロモナフト−2−アルデヒド、6,8−ジブロモナフト−2−アルデヒド、7,8−ジブロモナフト−2−アルデヒド、1,3,4−トリブロモナフト−2−アルデヒド、1,3,5−トリブロモナフト−2−アルデヒド、1,3,6−トリブロモナフト−2−アルデヒド、1,3,7−トリブロモナフト−2−アルデヒド、1,3,8−トリブロモナフト−2−アルデヒド、1,4,5−トリブロモナフト−2−アルデヒド、1,4,6−トリブロモナフト−2−アルデヒド、1,4,7−トリブロモナフト−2−アルデヒド、1,4,8−トリブロモナフト−2−アルデヒド、1,5,6−トリブロモナフト−2−アルデヒド、1,5,7−トリブロモナフト−2−アルデヒド、1,5,8−トリブロモナフト−2−アルデヒド、1,6,7−トリブロモナフト−2−アルデヒド、1,6,8−トリブロモナフト−2−アルデヒド、1,7,8−トリブロモナフト−2−アルデヒド、3,4,5−トリブロモナフト−2−アルデヒド、3,4,6−トリブロモナフト−2−アルデヒド、3,4,7−トリブロモナフト−2−アルデヒド、3,4,8−トリブロモナフト−2−アルデヒド、3,5,6−トリブロモナフト−2−アルデヒド、3,5,7−トリブロモナフト−2−アルデヒド、3,5,8−トリブロモナフト−2−アルデヒド、3,6,7−トリブロモナフト−2−アルデヒド、3,6,8−トリブロモナフト−2−アルデヒド、3,7,8−トリブロモナフト−2−アルデヒド、4,5,6−トリブロモナフト−2−アルデヒド、4,5,7−トリブロモナフト−2−アルデヒド、4,5,8−トリブロモナフト−2−アルデヒド、4,6,7−トリブロモナフト−2−アルデヒド、4,6,8−トリブロモナフト−2−アルデヒド、4,7,8−トリブロモナフト−2−アルデヒド、5,6,7−トリブロモナフト−2−アルデヒド、5,6,8−トリブロモナフト−2−アルデヒド、5,7,8−トリブロモナフト−2−アルデヒド、6,7,8−トリブロモナフト−2−アルデヒド、1−ヨードナフト−2−アルデヒド、3−ヨードナフト−2−アルデヒド、4−ヨードナフト−2−アルデヒド、5−ヨードナフト−2−アルデヒド、6−ヨードナフト−2−アルデヒド、7−ヨードナフト−2−アルデヒド、8−ヨードナフト−2−アルデヒド、1,3−ジヨードナフト−2−アルデヒド、1,4−ジヨードナフト−2−アルデヒド、1,5−ジヨードナフト−2−アルデヒド、1,6−ジヨードナフト−2−アルデヒド、1,7−ジヨードナフト−2−アルデヒド、1,8−ジヨードナフト−2−アルデヒド、3,4−ジヨードナフト−2−アルデヒド、3,5−ジヨードナフト−2−アルデヒド、3,6−ジヨードナフト−2−アルデヒド、3,7−ジヨードナフト−2−アルデヒド、3,8−ジヨードナフト−2−アルデヒド、4,5−ジヨードナフト−2−アルデヒド、4,6−ジヨードナフト−2−アルデヒド、4,7−ジヨードナフト−2−アルデヒド、4,8−ジヨードナフト−2−アルデヒド、5,6−ジヨードナフト−2−アルデヒド、5,7−ジヨードナフト−2−アルデヒド、5,8−ジヨードナフト−2−アルデヒド、6,7−ジヨードナフト−2−アルデヒド、6,8−ジヨードナフト−2−アルデヒド、7,8−ジヨードナフト−2−アルデヒド、1,3,4−トリヨードナフト−2−アルデヒド、1,3,5−トリヨードナフト−2−アルデヒド、1,3,6−トリヨードナフト−2−アルデヒド、1,3,7−トリヨードナフト−2−アルデヒド、1,3,8−トリヨードナフト−2−アルデヒド、1,4,5−トリヨードナフト−2−アルデヒド、1,4,6−トリヨードナフト−2−アルデヒド、1,4,7−トリヨードナフト−2−アルデヒド、1,4,8−トリヨードナフト−2−アルデヒド、1,5,6−トリヨードナフト−2−アルデヒド、1,5,7−トリヨードナフト−2−アルデヒド、1,5,8−トリヨードナフト−2−アルデヒド、1,6,7−トリヨードナフト−2−アルデヒド、1,6,8−トリヨードナフト−2−アルデヒド、1,7,8−トリヨードナフト−2−アルデヒド、3,4,5−トリヨードナフト−2−アルデヒド、3,4,6−トリヨードナフト−2−アルデヒド、3,4,7−トリヨードナフト−2−アルデヒド、3,4,8−トリヨードナフト−2−アルデヒド、3,5,6−トリヨードナフト−2−アルデヒド、3,5,7−トリヨードナフト−2−アルデヒド、3,5,8−トリヨードナフト−2−アルデヒド、3,6,7−トリヨードナフト−2−アルデヒド、3,6,8−トリヨードナフト−2−アルデヒド、3,7,8−トリヨードナフト−2−アルデヒド、4,5,6−トリヨードナフト−2−アルデヒド、4,5,7−トリヨードナフト−2−アルデヒド、4,5,8−トリヨードナフト−2−アルデヒド、4,6,7−トリヨードナフト−2−アルデヒド、4,6,8−トリヨードナフト−2−アルデヒド、4,7,8−トリヨードナフト−2−アルデヒド、5,6,7−トリヨードナフト−2−アルデヒド、5,6,8−トリヨードナフト−2−アルデヒド、5,7,8−トリヨードナフト−2−アルデヒド、6,7,8−トリヨードナフト−2−アルデヒド等が例示される。
以下実施例により本発明を具体的に説明するが、本発明はこれらの実施例のみに限定されるものではない。
SHIMAZU製LC−2010A。
ガラス製の反応器に2−アセチルナフタレン(30.0mg、0.18mmol)、N−3,5−ビス(トリフルオロメチル)ベンジルシンコニウムブロマイド(10.5mg、0.018mmol)、テトラメチルアンモニウムフルオライド(3.3mg、0.035mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を仕込み、窒素気流下、攪拌しながら−80℃とした後、これにトリフルオロメチルトリメチルシラン(52.2μl、0.35mmol)を加え、同温度で12時間反応を行った。反応終了後、室温に戻し、飽和塩化アンモニウム水溶液を添加、水層を酢酸エチル(5ml×2回)で抽出、硫酸マグネシウム上で乾燥、ろ過、濃縮の後、粗製の(R)−1,1,1−トリフルオロ−2−(ナフタレン−2イル)−1−トリメチルシロキシプロパンを得た。得られた粗製の(R)−1,1,1−トリフルオロ−2−(ナフタレン−2イル)−1−トリメチルシロキシプロパンは精製することなく、テトラ−n−ブチルアンモニウムフロオライド(50.6mg、0.19mmol)を溶解させたTHF(1.5ml)溶液を加え、攪拌しながら室温下で1時間攪拌を行った後、濃縮し得られた残渣はシリカゲルカラムクロマトグラフィー(アセトン/n−ヘキサン=10/1容量比)で精製することにより、目的物の(R)−1,1,1−トリフルオロ−2−(ナフタレン−2イル)プロパン−2−オール(41.7mg、収率98%)を白色固体として得た。
「α」D 25=+5.1(C=0.5,CHCl3)。
実施例1と同じ反応器を用い、触媒3,5−ビス(トリフルオロメチル)ベンジルシンコニウムブロマイド(10.5mg、0.018mmol)をN,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(15.0mg、0.018mmol)に替え、−80℃で6時間反応を行った以外は実施例1と同じ操作で(R)−1,1,1−トリフルオロ−2−(ナフタレン−2イル)プロパン−2−オール(36.9mg、収率87%)を白色固体として得た。得られた目的物の光学純度はHPLC測定において85%eeであった。
実施例1と同じ反応器を用い、触媒3,5−ビス(トリフルオロメチル)ベンジルシンコニウムブロマイド(10.5mg、0.018mmol)を鏡像体である3,5−ビス(トリフルオロメチル)ベンジルシンコニジウムブロマイド(10.5mg、0.018mmol)に替えた以外は実施例1と同じ操作で(S)−1,1,1−トリフルオロ−2−(ナフタレン−2イル)プロパン−2−オール(29.7mg、収率70%)を白色固体として得た。得られた目的物の光学純度はHPLC測定において77%eeであった。
実施例1と同じ反応装置を用い、溶剤をトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)よりトルエン/ジクロロメタン混合溶剤(1/1容量ml比、0.5)に替え、−60℃で8時間反応を行った以外、実施例1と同じ操作を行い、目的物(29.7mg、収率70%)を白色固体として得た。得られた目的物の光学純度は82%eeであった。
実施例1と同じ反応装置を用い、溶剤をトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)よりトルエン(0.5ml)に替え、−80℃で24時間反応を行った以外、実施例1と同じ操作を行い、目的物(12.7mg、収率30%)を白色固体として得た。得られた目的物の光学純度は72%eeであった。
実施例1と同じ反応装置を用い、溶剤をトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)よりジクロロメタン(0.5ml)に替え、−80℃で3時間反応を行った以外、実施例1と同じ操作を行い、目的物(23.4mg、収率56%)を白色固体として得た。得られた目的物の光学純度は71%eeであった。
ガラス製の反応器に2−アセチル−6−メトキシナフタレン(40.0mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(1.9mg、0.02mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で8時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1,1,1−トリフロロ−2−(6−メトキシナフタレン−2イル)プロパン−2−オール(40.0mg、収率74%)を白色固体として得た。
ガラス製の反応器に1−フェニルプロパン−1−オン(26.8mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(1.9mg、0.02mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で14時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1,1,1−トリフルオロ−2−フェニルブタン−2−オール(26.5mg、収率65%)を無色透明液体として得た。
ガラス製の反応器に1−フェニルブタン−1−オン(29.6mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(1.9mg、0.02mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で7時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1,1,1−トリフルオロ−2−フェニルペンタン−2−オール(36.4mg、収率83%)を無色透明液体として得た。
ガラス製の反応器に1−(メトキシフェニル)エタン−1−オン(30.0mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(3.8mg、0.04mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で7時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1,1,1−トリフルオロ−2−(4−メトキシフェニル)プロパン−2−オール(37.0mg、収率84%)を無色透明液体として得た。
ガラス製の反応器に1−(4−ブロモフェニル)エタン−1−オン(39.8mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(1.9mg、0.02mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で3時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1,1,1−トリフルオロ−2−(4−ブロモフェニル)プロパン−2−オール(43.1mg、収率81%)を無色透明液体として得た。
ガラス製の反応器に1−(4−クロロフェニル)エタン−1−オン(30.9mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(1.9mg、0.02mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で14時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1,1,1−トリフルオロ−2−(4−クロロフェニル)プロパン−2−オール(32.0mg、収率71%)を無色透明液体として得た。
ガラス製の反応器に1−(3−ブロモフェニル)エタン−1−オン(39.8mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(1.9mg、0.02mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で8時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1,1,1−トリフルオロ−2−(3−ブロモフェニル)プロパン−2−オール(39.2mg、収率73%)を淡黄色透明液体として得た。
ガラス製の反応器に1−(3−クロロフェニル)エタン−1−オン(30.9mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(3.8mg、0.04mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で4時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1,1,1−トリフルオロ−2−(3−クロロフェニル)プロパン−2−オール(32.0mg、収率71%)を無色透明液体として得た。
ガラス製の反応器に1−(3−ニトロフェニル)エタン−1−オン(33.0mg、0.20mmol)、N−3,5−ビス(トリフルオロメチル)ベンジルシンコニウムブロマイド(12.0mg、0.02mmol)、テトラメチルアンモニウムフルオライド(1.9mg、0.02mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)、トルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)及びモレキュラーシーブス4A(100mg)を用い、−60〜−50℃で7時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1,1,1−トリフルオロ−2−(3−ニトロフェニル)プロパン−2−オール(45.1mg、収率96%)を淡黄色透明液体として得た。
ガラス製の反応器に1−(4−ニトロフェニル)エタン−1−オン(33.0mg、0.20mmol)、N−3,5−ビス(トリフルオロメチル)ベンジルシンコニウムブロマイド(12.0mg、0.02mmol)、テトラメチルアンモニウムフルオライド(3.8mg、0.04mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で7時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1,1,1−トリフルオロ−2−(4−ニトロフェニル)プロパン−2−オール(45.6mg、収率97%)を白色固体として得た。
ガラス製の反応器に1−テトラロン(29.2mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(1.9mg、0.02mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で3時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1−トリフルオロメチル−1,2,3,4−テトラヒドロナフタレン−1−オール(32.3mg、収率75%)を白色固体として得た。
ガラス製の反応器に6−メトキシ−1−テトラロン(35.2mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(3.8mg、0.04mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−50〜−40℃で24時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−6−メトキシ−1−トリフルオロメチル−1,2,3,4−テトラヒドロナフタレン−1−オール(40.3mg、収率82%)を白色固体として得た。
ガラス製の反応器に1−インダノン(26.4mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(1.9mg、0.02mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で12時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−1−トリフルオロメチル−2,3−ジヒドロ−1H−インデン−1−オール(6.9mg、収率34%)を無色透明液体として得た。
ガラス製の反応器に(E)−4−フェニル−3−ブテン−2−オン(29.2mg、0.20mmol)、N,N’−(1,3−キシレン−1,3イル)−ビス(シンコニウムブロマイド)(17.1mg、0.02mmol)、テトラメチルアンモニウムフルオライド(1.9mg、0.02mmol)、トリフルオロメチルトリメチルシラン(59.1μl、0.40mmol)及びトルエン/ジクロロメタン混合溶剤(2/1容量比、0.5ml)を用い、−60〜−50℃で3時間反応を行った。実施例1と同じ後処理操作を行い、目的物の(R)−(E)−1−トリフルオロ−2−メチル−4−フェニル−3−ブテン−2−オール(36.7mg、収率85%)を無色透明液体として得た。
Claims (4)
- 一般式(1)
又は一般式(3)
を示し、R 1 とR 2 は同じ基であることはない。またR 1 とR 2 は縮環し炭素数4〜8の環状構造をとっても良い。]
で表されるカルボニル基含有化合物を、一般式(7)
、化学式(8)
で表されるアンモニウム塩存在下、一般式(5)
で表されるパーフルオロアルキルシラン類とを反応させ、次いで脱保護することを特徴とする一般式(6)
で表される光学活性パーフルオロアルキル基含有化合物の製造方法。 - 一般式(4)で示されるアンモニウム塩がテトラメチルアンモニウムフルオライド、テトラエチルアンモニウムフルオライド、テトラ−n−ブチルアンモニウムフルオライド又はオクタデシルトリメチルアンモニウムフルオライドであることを特徴とする請求項1に記載の光学活性パーフルオロアルキル基含有化合物の製造方法。
- 一般式(5)で表されるパーフルオロアルキルシラン類がトリフルオロメチルトリメチルシランであることを特徴とする請求項1又は請求項2に記載の光学活性パーフルオロアルキル基含有化合物の製造方法。
- 一般式(1)で表される化合物及び一般式(6)で表される化合物のR1がメチル基、エチル基、n−プロピル基又はi−プロピル基、R2が一般式(3)又は一般式(4)であることを特徴とする請求項1乃至請求項3のいずれか1項に記載の光学活性パーフルオロアルキル基含有化合物の製造方法。
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