JP2021165246A - Method for producing pentafluoroethyl group-containing alcohol, and intermediate compound for production of organic semiconductor material and enzymatic activity inhibitor - Google Patents
Method for producing pentafluoroethyl group-containing alcohol, and intermediate compound for production of organic semiconductor material and enzymatic activity inhibitor Download PDFInfo
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- JP2021165246A JP2021165246A JP2020069455A JP2020069455A JP2021165246A JP 2021165246 A JP2021165246 A JP 2021165246A JP 2020069455 A JP2020069455 A JP 2020069455A JP 2020069455 A JP2020069455 A JP 2020069455A JP 2021165246 A JP2021165246 A JP 2021165246A
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- JP
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- Prior art keywords
- pentafluoro
- propanol
- phenyl
- biphenyl
- trifluoromethyl
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 50
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 title claims abstract description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000000463 material Substances 0.000 title claims abstract description 9
- 239000004065 semiconductor Substances 0.000 title claims abstract description 9
- 239000003112 inhibitor Substances 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 title abstract description 27
- 230000002255 enzymatic effect Effects 0.000 title abstract 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 32
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims abstract description 16
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- -1 3,3,4,5,4-pentafluoro-2- (p-toluyl) -2-butanol Chemical compound 0.000 claims description 408
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 221
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 150000001298 alcohols Chemical class 0.000 claims description 30
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 19
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 16
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 14
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical group COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000543 intermediate Substances 0.000 claims description 13
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 13
- 150000002170 ethers Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 10
- 125000005504 styryl group Chemical group 0.000 claims description 8
- 102000004190 Enzymes Human genes 0.000 claims description 7
- 108090000790 Enzymes Proteins 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 125000006267 biphenyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- RRFWXUMMDZDOPE-UHFFFAOYSA-N 1-(3-chlorophenyl)-2,2,3,3,3-pentafluoro-1-phenylpropan-1-ol Chemical compound ClC=1C=C(C=CC=1)C(C(C(F)(F)F)(F)F)(O)C1=CC=CC=C1 RRFWXUMMDZDOPE-UHFFFAOYSA-N 0.000 claims description 4
- VDBDFXQBBOMPJI-UHFFFAOYSA-N 1-(4-bromophenyl)-2,2,3,3,3-pentafluoro-1-phenylpropan-1-ol Chemical compound BrC1=CC=C(C=C1)C(C(C(F)(F)F)(F)F)(O)C1=CC=CC=C1 VDBDFXQBBOMPJI-UHFFFAOYSA-N 0.000 claims description 4
- OUMIZAMRIZQLAK-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1,1-dipyridin-2-ylpropan-1-ol Chemical compound FC(C(O)(C1=NC=CC=C1)C1=NC=CC=C1)(C(F)(F)F)F OUMIZAMRIZQLAK-UHFFFAOYSA-N 0.000 claims description 4
- ZJCIIJIFYVGNGM-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-(4-nitrophenyl)-1-phenylpropan-1-ol Chemical compound FC(C(O)(C1=CC=CC=C1)C1=CC=C(C=C1)[N+](=O)[O-])(C(F)(F)F)F ZJCIIJIFYVGNGM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- MUDDYGJBUCHQIK-ZHACJKMWSA-N (E)-3-(4-bromophenyl)-4,4,5,5,5-pentafluoro-1-phenylpent-1-en-3-ol Chemical compound BrC1=CC=C(C=C1)C(/C=C/C1=CC=CC=C1)(C(C(F)(F)F)(F)F)O MUDDYGJBUCHQIK-ZHACJKMWSA-N 0.000 claims description 3
- HXNOXUCRHDBRHT-MDZDMXLPSA-N (E)-4,4,5,5,5-pentafluoro-1,3-bis(4-fluorophenyl)pent-1-en-3-ol Chemical compound FC(C(/C=C/C1=CC=C(C=C1)F)(O)C1=CC=C(C=C1)F)(C(F)(F)F)F HXNOXUCRHDBRHT-MDZDMXLPSA-N 0.000 claims description 3
- GZNONLUTNXIAIV-VAWYXSNFSA-N (E)-4,4,5,5,5-pentafluoro-3-(4-methoxyphenyl)-1-phenylpent-1-en-3-ol Chemical compound FC(C(/C=C/C1=CC=CC=C1)(O)C1=CC=C(C=C1)OC)(C(F)(F)F)F GZNONLUTNXIAIV-VAWYXSNFSA-N 0.000 claims description 3
- DAKRJZNQWCOQAC-UHFFFAOYSA-N 1-(4-chlorophenyl)-2,2,3,3,3-pentafluoro-1-phenylpropan-1-ol Chemical compound ClC1=CC=C(C=C1)C(C(C(F)(F)F)(F)F)(O)C1=CC=CC=C1 DAKRJZNQWCOQAC-UHFFFAOYSA-N 0.000 claims description 3
- VYITVYOHYMXQCK-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-[4-(trifluoromethoxy)phenyl]propan-1-ol Chemical compound FC(C(O)C1=CC=C(C=C1)OC(F)(F)F)(C(F)(F)F)F VYITVYOHYMXQCK-UHFFFAOYSA-N 0.000 claims description 3
- RPGYHNUBFRUSTM-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-phenyl-1-[4-(trifluoromethyl)phenyl]propan-1-ol Chemical compound FC(C(O)(C1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1)(C(F)(F)F)F RPGYHNUBFRUSTM-UHFFFAOYSA-N 0.000 claims description 3
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- SMFZUCFCWIVBQT-UHFFFAOYSA-N 3,3,4,4,4-pentafluoro-2-[4-(trifluoromethoxy)phenyl]butan-2-ol Chemical compound FC(C(C)(O)C1=CC=C(C=C1)OC(F)(F)F)(C(F)(F)F)F SMFZUCFCWIVBQT-UHFFFAOYSA-N 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- 239000008204 material by function Substances 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 229960005335 propanol Drugs 0.000 description 220
- 238000006243 chemical reaction Methods 0.000 description 79
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 70
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 69
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 68
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 66
- 238000005481 NMR spectroscopy Methods 0.000 description 52
- 150000002576 ketones Chemical class 0.000 description 45
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 37
- 238000005160 1H NMR spectroscopy Methods 0.000 description 34
- 239000012043 crude product Substances 0.000 description 24
- 239000007788 liquid Substances 0.000 description 22
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 11
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 11
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012965 benzophenone Substances 0.000 description 8
- 125000006501 nitrophenyl group Chemical group 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 125000004799 bromophenyl group Chemical group 0.000 description 7
- 125000001207 fluorophenyl group Chemical group 0.000 description 7
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 7
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 6
- 238000006692 trifluoromethylation reaction Methods 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 125000000068 chlorophenyl group Chemical group 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- ROUASDCATPIGEX-VAWYXSNFSA-N (E)-4,4,5,5,5-pentafluoro-1,3-diphenylpent-1-en-3-ol Chemical compound FC(C(/C=C/C1=CC=CC=C1)(O)C1=CC=CC=C1)(C(F)(F)F)F ROUASDCATPIGEX-VAWYXSNFSA-N 0.000 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 235000005513 chalcones Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 3
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 3
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 2
- JGTWMMODPIQBET-ZHACJKMWSA-N (E)-3-(4-chlorophenyl)-4,4,5,5,5-pentafluoro-1-phenylpent-1-en-3-ol Chemical compound ClC1=CC=C(C=C1)C(/C=C/C1=CC=CC=C1)(C(C(F)(F)F)(F)F)O JGTWMMODPIQBET-ZHACJKMWSA-N 0.000 description 2
- VODPJCKEEANQDP-ZHACJKMWSA-N (E)-4,4,5,5,5-pentafluoro-3-(4-nitrophenyl)-1-phenylpent-1-en-3-ol Chemical compound FC(C(/C=C/C1=CC=CC=C1)(O)C1=CC=C(C=C1)[N+](=O)[O-])(C(F)(F)F)F VODPJCKEEANQDP-ZHACJKMWSA-N 0.000 description 2
- DYXXNSAGHQDLEA-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethylsulfonylbenzene Chemical compound FC(F)(F)C(F)(F)S(=O)(=O)C1=CC=CC=C1 DYXXNSAGHQDLEA-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- YIUNDVILTVRLIN-UHFFFAOYSA-N 1-(4-bromophenyl)-2,2,3,3,3-pentafluoropropan-1-ol Chemical compound FC(F)(F)C(F)(F)C(O)C1=CC=C(Br)C=C1 YIUNDVILTVRLIN-UHFFFAOYSA-N 0.000 description 2
- MJZYEOYNWIIQIV-UHFFFAOYSA-N 2,2,2-trifluoro-1,1-diphenylethanol Chemical compound C=1C=CC=CC=1C(C(F)(F)F)(O)C1=CC=CC=C1 MJZYEOYNWIIQIV-UHFFFAOYSA-N 0.000 description 2
- QOBLARAJKUCHMF-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1,1-diphenylpropan-1-ol Chemical compound C=1C=CC=CC=1C(C(F)(F)C(F)(F)F)(O)C1=CC=CC=C1 QOBLARAJKUCHMF-UHFFFAOYSA-N 0.000 description 2
- JIGOBHNMBOKQNP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-(4-fluorophenyl)propan-1-ol Chemical compound FC(F)(F)C(F)(F)C(O)C1=CC=C(F)C=C1 JIGOBHNMBOKQNP-UHFFFAOYSA-N 0.000 description 2
- FCHQTFUTMKUGSY-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-(4-iodophenyl)propan-1-ol Chemical compound FC(C(O)C1=CC=C(C=C1)I)(C(F)(F)F)F FCHQTFUTMKUGSY-UHFFFAOYSA-N 0.000 description 2
- QBZQWLDZDOYMQN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-(4-methylphenyl)propan-1-ol Chemical compound CC1=CC=C(C(O)C(F)(F)C(F)(F)F)C=C1 QBZQWLDZDOYMQN-UHFFFAOYSA-N 0.000 description 2
- UFCMINNRLVINEN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-(furan-3-yl)-1-phenylpropan-1-ol Chemical compound OC(C(C(F)(F)F)(F)F)(C1=COC=C1)C1=CC=CC=C1 UFCMINNRLVINEN-UHFFFAOYSA-N 0.000 description 2
- GXPSVDOFDBKGRZ-UHFFFAOYSA-N 2,2,3,3,3-pentafluoro-1-phenyl-1-thiophen-3-ylpropan-1-ol Chemical compound OC(C(C(F)(F)F)(F)F)(C1=CSC=C1)C1=CC=CC=C1 GXPSVDOFDBKGRZ-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
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical group ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical group O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 2
- LCRCBXLHWTVPEQ-UHFFFAOYSA-N 2-phenylbenzaldehyde Chemical group O=CC1=CC=CC=C1C1=CC=CC=C1 LCRCBXLHWTVPEQ-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- HYDWALOBQJFOMS-UHFFFAOYSA-N 3,6,9,12,15-pentaoxaheptadecane Chemical compound CCOCCOCCOCCOCCOCC HYDWALOBQJFOMS-UHFFFAOYSA-N 0.000 description 2
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
- KMEGBWQYOBNDAA-UHFFFAOYSA-N 9-(1,1,2,2,2-pentafluoroethyl)fluoren-9-ol Chemical compound C1=CC=C2C(O)(C(F)(F)C(F)(F)F)C3=CC=CC=C3C2=C1 KMEGBWQYOBNDAA-UHFFFAOYSA-N 0.000 description 2
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- KUCXNAXAAXKXGV-UHFFFAOYSA-N pyridin-3-yl-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)C1=CC=CN=C1 KUCXNAXAAXKXGV-UHFFFAOYSA-N 0.000 description 1
- QHEFLWVQQBTZDP-UHFFFAOYSA-N pyridin-4-yl(thiophen-2-yl)methanone Chemical compound C=1C=NC=CC=1C(=O)C1=CC=CS1 QHEFLWVQQBTZDP-UHFFFAOYSA-N 0.000 description 1
- VBWNWEIBAXXUIG-UHFFFAOYSA-N pyridin-4-yl(thiophen-3-yl)methanone Chemical compound C=1C=NC=CC=1C(=O)C=1C=CSC=1 VBWNWEIBAXXUIG-UHFFFAOYSA-N 0.000 description 1
- JDLPMVRJKVZHJR-UHFFFAOYSA-N pyridin-4-yl-[2-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)C1=CC=NC=C1 JDLPMVRJKVZHJR-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 241000894007 species Species 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
- HZSMAMMINJXQME-UHFFFAOYSA-N thiophen-2-yl-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)C=2SC=CC=2)=C1 HZSMAMMINJXQME-UHFFFAOYSA-N 0.000 description 1
- GNYVKGOINXAFFH-UHFFFAOYSA-N thiophen-2-yl-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)C1=CC=CS1 GNYVKGOINXAFFH-UHFFFAOYSA-N 0.000 description 1
- QFUBEOXTTUOKAN-UHFFFAOYSA-N thiophen-3-yl-[2-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)C1=CSC=C1 QFUBEOXTTUOKAN-UHFFFAOYSA-N 0.000 description 1
- TVGQMPOWWKQBIS-UHFFFAOYSA-N thiophen-3-yl-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)C1=CSC=C1 TVGQMPOWWKQBIS-UHFFFAOYSA-N 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本発明はペンタフルオロエタンを原料とし、ペンタフルオロエチルアニオンを発生させ、カルボニル化合物類に求核的ペンタフルオロエチル化を行い、ペンタフルオロエチル基含有アルコール類を製造する方法に関する。ペンタフルオロエチル基含有アルコール類は医薬、農薬、高分子機能性材料として有用な化合物である。
さらに本発明は、有機半導体材料および酵素活性阻害剤の製造中間体化合物に関する。
The present invention relates to a method for producing pentafluoroethyl group-containing alcohols by generating pentafluoroethyl anions from pentafluoroethane as a raw material and nucleophilic pentafluoroethylation of carbonyl compounds. Pentafluoroethyl group-containing alcohols are compounds useful as pharmaceuticals, pesticides, and polymer functional materials.
Furthermore, the present invention relates to organic semiconductor materials and intermediate compounds for the production of enzyme activity inhibitors.
従来、ペンタフルオロエチル基の導入方法としては、ペンタフルオロエチルトリメチルシラン、フッ化カリウム、ホウ酸エステルを反応させペンタフルオロエチルボレート塩にした後、カルボニル化合物類と反応させる方法(例えば、非特許文献1)やペンタフルオロエチルフェニルスルホンとアルコキシドから反応系中でペンタフルオロエチルアニオンを発生させた後、カルボニル化合物類と反応と反応させる方法(例えば、非特許文献2)が知られている。 Conventionally, as a method for introducing a pentafluoroethyl group, a method of reacting pentafluoroethyltrimethylsilane, potassium fluoride, and borate ester to form a pentafluoroethylborate salt and then reacting with carbonyl compounds (for example, non-patent documents). A method is known in which a pentafluoroethyl anion is generated in a reaction system from 1) or pentafluoroethylphenyl sulfone and an alkoxide and then reacted with a carbonyl compound (for example, Non-Patent Document 2).
また、ペンタフルオロエタンを原料としペンタフルオロエチルアニオンを発生させ、カルボニル化合物類に求核的ペンタフルオロエチル化を行い、ペンタフルオロエチル基含有アルコール類を製造する方法としては、塩基にカリウムtert−ブトキシド、溶媒にジメチルホルムアミドを用いる方法(例えば、非特許文献3)や塩基に水酸化カリウム、溶媒にジメチルスルホキシドを用いる方法(例えば、特許文献1)等が知られている。 In addition, as a method for producing pentafluoroethyl group-containing alcohols by generating pentafluoroethyl anion from pentafluoroethane as a raw material and nucleophilic pentafluoroethylation of carbonyl compounds, potassium tert-butoxide is used as a base. , A method using dimethylformamide as a solvent (for example, Non-Patent Document 3), a method using potassium hydroxide as a base, and a method using dimethyl sulfoxide as a solvent (for example, Patent Document 1) are known.
従来の非特許文献1及び2に記載の方法は、ペンタフルオロエチル源であるペンタフルオロトリエチルトリメチルシラン、ペンタフルオロエチルフェニルスルホンが比較的高価かつ工業的にも入手困難という課題がある。一方、非特許文献3、特許文献1及び特許文献2に記載の方法では、収率が比較的低いこと、さらには、カルボニル化合物類への適用範囲が狭いという課題がある。 The conventional methods described in Non-Patent Documents 1 and 2 have a problem that pentafluorotriethyltrimethylsilane and pentafluoroethylphenylsulfone, which are pentafluoroethyl sources, are relatively expensive and industrially difficult to obtain. On the other hand, the methods described in Non-Patent Document 3, Patent Document 1 and Patent Document 2 have problems that the yield is relatively low and the range of application to carbonyl compounds is narrow.
また、特許文献3には、カルボニル化合物より、多価エーテル及び還元剤存在下で、トリフルオロメタンを反応させて、トリフルオロメチル基含有アルコール類を製造する方法が開示されている。
ここで、カルボニル化合物のトリフルオロメチル化とペンタフルオロエチル化との対比となるが、カルボニル化合物のトリフルオロメチル化によりトリフルオロメチル基含有アルコール類を製造できるとしても、直ちにカルボニル化合物をペンタフルオロエチル化してペンタフルオロエチル基含有アルコール類を製造できるわけではない。
Further, Patent Document 3 discloses a method for producing trifluoromethyl group-containing alcohols by reacting a carbonyl compound with trifluoromethane in the presence of a polyvalent ether and a reducing agent.
Here, the comparison between trifluoromethylation and pentafluoroethylation of the carbonyl compound is made. Even if trifluoromethyl group-containing alcohols can be produced by trifluoromethylation of the carbonyl compound, the carbonyl compound is immediately converted to pentafluoroethyl. It is not possible to produce pentafluoroethyl group-containing alcohols.
すなわち非特許文献4のアブストラクトなどには、有機化合物の選択的なフルオロアルキル化反応は、フッ素原子の電気陰性度の影響を受けることが記載されている。具体的には、(1)フッ素原子の数、(2)有機化合物中の反応部位の構造、(3)炭素−金属結合に係る場合には金属対イオンの違いおよび(4)カルベン種の生成による促進化が挙げられており、カルボニル化合物のトリフルオロメチル化とペンタフルオロエチル化との対比の観点では、(1)フッ素原子の数も考慮すべき要素と考えられる。 That is, it is described in the abstract of Non-Patent Document 4 and the like that the selective fluoroalkylation reaction of an organic compound is affected by the electronegativity of a fluorine atom. Specifically, (1) the number of fluorine atoms, (2) the structure of the reaction site in the organic compound, (3) the difference in metal vs. ion in the case of a carbon-metal bond, and (4) the formation of carbene species. From the viewpoint of comparison between trifluoromethylation and pentafluoroethylation of carbonyl compounds, (1) the number of fluorine atoms is also considered to be a factor to be considered.
非特許文献5の表2には、下記反応式について、トリフルオロメチル化(CF3化)とペンタフルオロエチル化(C2F5化)の結果が示されている。
また非特許文献6の表1には、下記反応式(TMSCF3からCuCF2CF3の調製)について、得られた生成物と副生物の収率の結果が示されている。
Entry1;82%, 4%,n.d.(検出限界以下)
Entry2; 5%,75%, 7.5%
Entry3;14%,52%, 4.5%
Entry4; 4%,33%,n.d.
Entry5;66%, 3%,13.5%
この結果は、トリフルオロメチル化(CF3化)とペンタフルオロエチル化(C2F5化)の反応性が大きく異なっており、新たにペンタフルオロエチル化(C2F5化)反応を行なう場合には、既存のトリフルオロメチル化(CF3化)反応を把握していたとしても、ペンタフルオロエチル化(C2F5化)反応の収率等の予測が困難であって、試行する必要があることを示すことを意味する。
In addition, Table 1 of Non-Patent Document 6 shows the results of the yields of the obtained products and by-products for the following reaction formula (preparation of CuCF 2 CF 3 from TM SCF 3).
Entry1; 82%, 4%, n. d. (Below the detection limit)
Entry2; 5%, 75%, 7.5%
Entry3; 14%, 52%, 4.5%
Entry4; 4%, 33%, n. d.
Entry5; 66%, 3%, 13.5%
As a result, the reactivity of trifluoromethylation (CF3 conversion) and pentafluoroethylation (C2F5 conversion) is significantly different, and when a new pentafluoroethylation (C2F5 conversion) reaction is carried out, the existing bird is used. Even if the fluoromethylation (CF3 conversion) reaction is known, it means that it is difficult to predict the yield of the pentafluoroethylation (C2F5 conversion) reaction and the like, and it is necessary to try it.
上記の背景において、医薬、農薬、高分子機能性材料として有用な化合物であるペンタフルオロエチル基含有アルコール類を、ペンタフルオロエチル化反応により効率的に製造する方法を確立すること、さらにこのような反応を用いて新規な有機半導体材料および酵素活性阻害剤の製造中間体化合物が望まれていた。 Against the above background, establishing a method for efficiently producing pentafluoroethyl group-containing alcohols, which are useful compounds as pharmaceuticals, pesticides, and polymer functional materials, by a pentafluoroethylation reaction, and further, such Production intermediate compounds for novel organic semiconductor materials and enzyme activity inhibitors using the reaction have been desired.
本発明の目的は、工業的に適用できるペンタフルオルエチル基含有アルコール類の製造方法を提供することにある。
また本発明は有機半導体材料および酵素活性阻害剤の製造中間体化合物を提供することにある。
An object of the present invention is to provide an industrially applicable method for producing a pentafluorethyl group-containing alcohol.
The present invention also provides an intermediate compound for producing an organic semiconductor material and an enzyme activity inhibitor.
本発明者らは、冷媒として工業的に用いられている比較的安価なペンタフルオロエタンをペンタフルオロエチルアニオンの発生剤として用いるための原料とし、さらに比較的に安価なカリウムtert−ブトキシドもしくはカリウムヘキサメチルジシラジドを用い、カルボニル化合物類のペンタフルオロエチル化が可能な条件について鋭意検討した。
その結果、反応系に多価エーテル化合物を共存させることにより、室温もしくは低温下において、カルボニル化合物類のペンタフルオロエチル化を行なったところ、高収率で目的物のペンタフルオロエチル基含有化合物が得られることを見出し、本発明を完成させるに至った。
The present inventors use relatively inexpensive pentafluoroethane, which is industrially used as a refrigerant, as a raw material for use as a generator of pentafluoroethyl anion, and further inexpensive potassium tert-butoxide or potassium hexa. Using methyldisilazide, we diligently investigated the conditions under which carbonyl compounds can be pentafluoroethylated.
As a result, when the carbonyl compounds were pentafluoroethylated at room temperature or low temperature by coexisting the polyvalent ether compound in the reaction system, the desired pentafluoroethyl group-containing compound was obtained in high yield. It was found that this was possible, and the present invention was completed.
すなわち本発明は、下記一般式(1)
で表されるカルボニル化合物類を、有機溶剤中、多価エーテル類及びカリウムtert−ブトキシドもしくはカリウムヘキサメチルジシラジド存在下、ペンタフルオロエタンと反応させることを特徴とする、下記一般式(2)
で表されるペンタフルオロエチル基含有アルコール類の製造方法に係る。
That is, the present invention has the following general formula (1).
The following general formula (2) is characterized in that the carbonyl compounds represented by are reacted with pentafluoroethane in the presence of polyvalent ethers and potassium tert-butoxide or potassium hexamethyldisilazide in an organic solvent.
The present invention relates to a method for producing a pentafluoroethyl group-containing alcohol represented by.
また本発明は、上記一般式(1)
で表されるカルボニル化合物類を、有機溶剤中、多価エーテル類及びカリウムtert−ブトキシドもしくはカリウムヘキサメチルジシラジド存在下、ペンタフルオロエタンと反応させる、上記のペンタフルオロエチル基含有アルコール類の製造方法に係る。
Further, the present invention has the above general formula (1).
Production of the above-mentioned pentafluoroethyl group-containing alcohols by reacting the carbonyl compounds represented by (1) with pentafluoroethane in the presence of polyhydric ethers and potassium tert-butoxide or potassium hexamethyldisilazide in an organic solvent. It concerns the method.
上記の多価エーテル類は、1,2−ジメトキシエタン又は1,2−ジエトキシエタンであること、あるいは、トリエチレングリコールジメチルエーテル又はテトラエチレングリコールジエチルエーテルであることが好ましい。 The polyvalent ethers described above are preferably 1,2-dimethoxyethane or 1,2-diethoxyethane, or are preferably triethylene glycol dimethyl ether or tetraethylene glycol diethyl ether.
また本発明は、多価エーテル類をカリウムtertブトキシド又はカリウムヘキサメチルジシラジドに対して4.0モル倍量以上使用する、上記のペンタフルオロエチル基含有アルコール類の製造方法に係る。 The present invention also relates to the above-mentioned method for producing pentafluoroethyl group-containing alcohols, in which polyhydric ethers are used in an amount of 4.0 mol times or more the amount of potassium tert-butoxide or potassium hexamethyldisilazide.
また本発明は、多価エーテル類を反応溶剤として使用する、上記のペンタフルオロエチル基含有アルコール類の製造方法に係る。 The present invention also relates to the above method for producing pentafluoroethyl group-containing alcohols using polyvalent ethers as a reaction solvent.
上記の有機溶剤は、化学反応に一般的に用いられる有機溶媒であれば特に制限はなく、例えば、ジエチルエーテル、テトラヒドロフラン、メチルtertブチルエーテル等のエーテル系溶媒やn−ヘキサン、n−ヘプタン、n−オクタン、n−デカン、シクロヘキサン、メチルシクロヘキサン、シクロオクタン等の炭化水素系溶媒やベンゼン、トルエン、キシレン等の芳香族系溶媒やジクロロメタン、クロロホルム、1,1,2,2−ジクロロエタン、1,1,2,2−ジブロモエタン等のハロゲン系溶媒、さらには、N,N−ジメチルホルムアミド、ジメチルスルホキシド等の高極性溶媒も使用できる。 The above organic solvent is not particularly limited as long as it is an organic solvent generally used for chemical reactions. For example, an ether solvent such as diethyl ether, tetrahydrofuran, methyl tert butyl ether, n-hexane, n-heptane, n- Hydrocarbon solvents such as octane, n-decane, cyclohexane, methylcyclohexane and cyclooctane, aromatic solvents such as benzene, toluene and xylene, dichloromethane, chloroform, 1,1,2,2-dichloroethane, 1,1,1 Halogen-based solvents such as 2,2-dibromoethane, and highly polar solvents such as N, N-dimethylformamide and dimethylsulfoxide can also be used.
また本発明は、有機半導体材料を製造するための新規な中間体化合物として、下記化合物からなるペンタフルオロエチル基含有アルコール化合物に係る。
2,2,3,3,3−ペンタフルオロ−1−(4−(トリフルオロメトキシ)フェニル)−1−プロパノール、
2,2,3,3,3−ペンタフルオロ−1−(4−ヨードフェニル)−1−プロパノール、
2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−(トリフルオロメチル)フェニル)−1−プロパノール、
1−(4−ブロモフェニル)−2,2,3,3,3−ペンタフルオロ−1−フェニル−1−プロパノール、
1−(4−クロロフェニル)−2,2,3,3,3−ペンタフルオロ−1−フェニル−1−プロパノール、
1−(3−クロロフェニル)−2,2,3,3,3−ペンタフルオロ−1−フェニル−1−プロパノール、
2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−フェニル−1−プロパノール、
2,2,3,3,3−ペンタフルオロ−1,1−ジ(ピリジン−2−イル)−1−プロパノール、
(E)−4,4,5,5,5−ペンタフルオロ−1,3−ジフェニル−1−ペンテン−3−オール、
(E)−4,4,5,5,5−ペンタフルオロ−1,3−ビス(4−フルオロフェニル)−1−ペンテン−3−オール、
(E)−3−(4−ブロモフェニル)−4,4,5,5,5−ペンタフルオロ−1−フェニル−1−ペンテン−3−オール、
(E)−4,4,5,5,5−ペンタフルオロ−3−(4−メトキシフェニル)−1−フェニル−1−ペンテン−3−オール、
(E)−3−(4−クロロフェニル)−4,4,5,5,5−ペンタフルオロ−1−フェニル−1−ペンテン−3−オール、
(E)−4,4,5,5,5−ペンタフルオロ−3−(4−ニトロフェニル)−1−フェニル−1−ペンテン−3−オール。
The present invention also relates to a pentafluoroethyl group-containing alcohol compound composed of the following compounds as a novel intermediate compound for producing an organic semiconductor material.
2,2,3,3,3-pentafluoro-1- (4- (trifluoromethoxy) phenyl) -1-propanol,
2,2,3,3,3-pentafluoro-1- (4-iodophenyl) -1-propanol,
2,2,3,3,3-pentafluoro-1-phenyl-1- (4- (trifluoromethyl) phenyl) -1-propanol,
1- (4-Bromophenyl) -2,2,3,3,3-pentafluoro-1-phenyl-1-propanol,
1- (4-chlorophenyl) -2,2,3,3,3-pentafluoro-1-phenyl-1-propanol,
1- (3-chlorophenyl) -2,2,3,3,3-pentafluoro-1-phenyl-1-propanol,
2,2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1-phenyl-1-propanol,
2,2,3,3,3-pentafluoro-1,1-di (pyridin-2-yl) -1-propanol,
(E) -4,4,5,5,5-pentafluoro-1,3-diphenyl-1-pentene-3-ol,
(E) -4,4,5,5,5-pentafluoro-1,3-bis (4-fluorophenyl) -1-pentene-3-ol,
(E) -3- (4-Bromophenyl) -4,4,5,5,5-pentafluoro-1-phenyl-1-pentene-3-ol,
(E) -4,4,5,5,5-pentafluoro-3- (4-methoxyphenyl) -1-phenyl-1-pentene-3-ol,
(E) -3- (4-chlorophenyl) -4,4,5,5,5-pentafluoro-1-phenyl-1-pentene-3-ol,
(E) -4,4,5,5,5-pentafluoro-3- (4-nitrophenyl) -1-phenyl-1-pentene-3-ol.
上記の本発明に係る有機半導体材料の製造中間体としてのペンタフルオロエチル基含有アルコール化合物は、例えば国際公開第2013/122174号の段落0062の含フッ素芳香族化合物の製造ルートにおいて、その中間化合物である1−1Bで示す化合物を製造するのに好適な化合物である。 The pentafluoroethyl group-containing alcohol compound as the above-mentioned production intermediate for the organic semiconductor material according to the present invention is, for example, an intermediate compound in the production route of the fluorine-containing aromatic compound in paragraph 0062 of International Publication No. 2013/122174. It is a compound suitable for producing the compound represented by a certain 1-1B.
また本発明は、PI3キナーゼ等の酵素の活性を阻害する薬剤を製造するための新規な中間体化合物として、下記化合物からなるペンタフルオロエチル基含有アルコール化合物に係る。
2−(4−クロロフェニル)−3,3,4,4,4−ペンタフルオロ−2−ブタノール、
2−(3−クロロフェニル)−3,3,4,4,4−ペンタフルオロ−2−ブタノール、
2−(4−ブロモフェニル)−3,3,4,4,4−ペンタフルオロ−2−ブタノール、
3,3,4,4,4−ペンタフルオロ−2−(p−トルイル)−2−ブタノール、
3,3,4,4,4−ペンタフルオロ−2−(4−(トリフルオロメチル)フェニル)−2−ブタノール、
3,3,4,4,4−ペンタフルオロ−2−(4−(トリフルオロメトキシ)フェニル)−2−ブタノール。
The present invention also relates to a pentafluoroethyl group-containing alcohol compound composed of the following compounds as a novel intermediate compound for producing a drug that inhibits the activity of an enzyme such as PI3 kinase.
2- (4-chlorophenyl) -3,3,4,5,4-pentafluoro-2-butanol,
2- (3-Chlorophenyl) -3,3,4,5,4-pentafluoro-2-butanol,
2- (4-Bromophenyl) -3,3,4,5,4-pentafluoro-2-butanol,
3,3,4,5,4-Pentafluoro-2- (p-toluyl) -2-butanol,
3,3,4,5,4-Pentafluoro-2- (4- (trifluoromethyl) phenyl) -2-butanol,
3,3,4,5,4-Pentafluoro-2- (4- (trifluoromethoxy) phenyl) -2-butanol.
上記の本発明に係る酵素活性阻害剤の製造中間体としてのペンタフルオロエチル基含有アルコール化合物は、例えば国際公開第2019/079469号の第96頁のスキーム VI.(Scheme VI.)において、その中間化合物である1−2で示す化合物を製造するのに好適な化合物である。 The pentafluoroethyl group-containing alcohol compound as an intermediate for the production of the enzyme activity inhibitor according to the present invention is described in, for example, the scheme VI. In (Scheme VI.), It is a suitable compound for producing the compound represented by 1-2, which is an intermediate compound thereof.
本発明により、冷媒として工業的に用いられている比較的安価なペンタフルオロエタンを用い、室温下、カルボニル化合物類のペンタフルオロエチル化を行なうことで、高収率でペンタフルオロエタン基含有アルコール類が得られ、工業的に適用できるペンタフルオルエチル基含有アルコール類の製造方法が提供できる。
また本発明により、産業上有用な有機半導体材料を製造するための新規な中間体化合物や、医薬、農薬分野において有用な酵素活性阻害剤を製造するための新規な中間体化合物を提供することができる。
According to the present invention, pentafluoroethane group-containing alcohols are produced in high yield by pentafluoroethylation of carbonyl compounds at room temperature using relatively inexpensive pentafluoroethane industrially used as a refrigerant. Is obtained, and an industrially applicable method for producing a pentafluoroethyl group-containing alcohol can be provided.
Further, according to the present invention, it is possible to provide a novel intermediate compound for producing an organic semiconductor material useful in industry and a novel intermediate compound for producing an enzyme activity inhibitor useful in the fields of medicine and agrochemicals. can.
以下、本発明を詳細に説明する。
本発明に係る製造方法において、用いられるカルボニル化合物類は、下記一般式(1)
The carbonyl compounds used in the production method according to the present invention are described in the following general formula (1).
この内、置換基を有してもよいフェニル基としては、フェニル基、2−メチルフェニル基、3−メチルフェニル基、4−メチルフェニル基、2−メトキシフェニル基、3−メトキシフェニル基、4−メトキシフェニル基、2−フルオロフェニル基、3−フルオロフェニル基、4−フルオロフェニル基、2−クロロフェニル基、3−クロロフェニル基、4−クロロフェニル基、2−ブロモフェニル基、3−ブロモフェニル基、4−ブロモフェニル基、2−(トリフルオロメチル)フェニル基、3−(トリフルオロメチル)フェニル基、4−(トリフルオロメチル)フェニル基、2−ジメチルアミノフェニル基、3−ジメチルアミノフェニル基、4−ジメチルアミノフェニル基、2−ニトロフェニル基、3−ニトロフェニル基、4−ニトロフェニル基などが挙げられる。
また、ピリジル基としては、2−ピリジル基、3−ピリジル基、4−ピリジル基などが挙げられる。フリル基としては、2−フリル基、3−フリル基などが挙げられる。チエニル基としては、2−チエニル基、3−チエニル基などが挙げられる。ビフェニル基としては、2−ビフェニル基、3−ビフェニル基、4−ビフェニル基などが挙げられる。
置換基を有してもよいスチリル基としては、スチリル基以外にも、2−フルオロスチリル基、3−フルオロスチリル基、4−フルオロスチリル基などが挙げられる。
炭素数1〜9の直鎖状もしくは分岐状もしくは環状の脂肪族アルキル基としては、メチル基、エチル基、n−プロピル基、iso−プロピル、n−ブチル基、tert−ブチル基、sec−ブチル基、n−ペンチル基、n−ヘキシル基、n−へプチル基、n−オクチル基、n−ノニル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロへプチル基、シクロオクチル基、シクロノニル基などが挙げられる。
Among these, phenyl groups that may have a substituent include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2-methoxyphenyl group, a 3-methoxyphenyl group, and 4 -Methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-Bromophenyl group, 2- (trifluoromethyl) phenyl group, 3- (trifluoromethyl) phenyl group, 4- (trifluoromethyl) phenyl group, 2-dimethylaminophenyl group, 3-dimethylaminophenyl group, Examples thereof include 4-dimethylaminophenyl group, 2-nitrophenyl group, 3-nitrophenyl group and 4-nitrophenyl group.
Moreover, as a pyridyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group and the like can be mentioned. Examples of the frill group include a 2-frill group and a 3-frill group. Examples of the thienyl group include a 2-thienyl group and a 3-thienyl group. Examples of the biphenyl group include a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group and the like.
Examples of the styryl group which may have a substituent include a 2-fluorostyryl group, a 3-fluorostyryl group, a 4-fluorostyryl group and the like, in addition to the styryl group.
Linear, branched or cyclic aliphatic alkyl groups having 1 to 9 carbon atoms include methyl group, ethyl group, n-propyl group, iso-propyl, n-butyl group, tert-butyl group and sec-butyl group. Group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, Cyclononyl group and the like can be mentioned.
本発明の製造方法に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1がフェニル基である化合物としては、具体的には例えば、ベンズアルデヒド、ベンゾフェノン、2−メチルベンゾフェノン、3−メチルベンゾフェノン、4−メチルベンゾフェノン、2−メトキシベンゾフェノン、3−メトキシベンゾフェノン、4−メトキシベンゾフェノン、2−フルオロベンゾフェノン、3−フルオロベンゾフェノン、4−フルオロベンゾフェノン、2−クロロベンゾフェノン、3−クロロベンゾフェノン、4−クロロベンゾフェノン、2−ブロモベンゾフェノン、3−ブロモベンゾフェノン、4−ブロモベンゾフェノン、2−(トリフルオロメチル)ベンゾフェノン、3−(トリフルオロメチル)ベンゾフェノン、4−(トリフルオロメチル)ベンゾフェノン、2−ジメチルアミノベンゾフェノン、3−ジメチルアミノベンゾフェノン、4−ジメチルアミノベンゾフェノン、2−ニトロベンゾフェノン、3−ニトロベンゾフェノン、4−ニトロベンゾフェノン、2−ベンゾイルピリジン、3−ベンゾイルピリジン、4−ベンゾイルピリジン、2−ベンゾイルフラン、3−ベンゾイルフラン、2−ベンゾイルチオフェン、3−ベンゾイルチオフェン、2−ベンゾイルビフェニル、3−ベンゾイルビフェニル、4−ベンゾイルビフェニル、カルコン、2−フルオロカルコン、3−フルオロカルコン、4−フルオロカルコン、2,2−ジメチルプロピオフェノン等が挙げられる。 Specific examples of the carbonyl compounds represented by the general formula (1) applicable to the production method of the present invention in which R 1 is a phenyl group include benzaldehyde, benzophenone, 2-methylbenzophenone, and 3-. Methylbenzophenone, 4-methylbenzophenone, 2-methoxybenzophenone, 3-methoxybenzophenone, 4-methoxybenzophenone, 2-fluorobenzophenone, 3-fluorobenzophenone, 4-fluorobenzophenone, 2-chlorobenzophenone, 3-chlorobenzophenone, 4- Chlorobenzophenone, 2-bromobenzophenone, 3-bromobenzophenone, 4-bromobenzophenone, 2- (trifluoromethyl) benzophenone, 3- (trifluoromethyl) benzophenone, 4- (trifluoromethyl) benzophenone, 2-dimethylaminobenzophenone , 3-Dimethylaminobenzophenone, 4-dimethylaminobenzophenone, 2-nitrobenzophenone, 3-nitrobenzophenone, 4-nitrobenzophenone, 2-benzoylpyridine, 3-benzoylpyridine, 4-benzoylpyridine, 2-benzoylfuran, 3- Benzophenone, 2-benzoylthiophenone, 3-benzoylthiophenone, 2-benzoylbiphenyl, 3-benzoylbiphenyl, 4-benzoylbiphenyl, chalcone, 2-fluorochalcone, 3-fluorochalcone, 4-fluorochalcone, 2,2-dimethyl Propiophenone and the like can be mentioned.
発明の製造に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1及び/又はR2がメチルフェニル基である化合物としては、具体的には例えば、2−メチルベンズアルデヒド、3−メチルベンズアルデヒド、4−メチルベンズアルデヒド、2,2´−ジメチルベンゾフェノン、2,3´−ジメチルベンゾフェノン、2,4´−ジメチルベンゾフェノン、3,3´−ジメチルベンゾフェノン、3,4´−ジメチルベンゾフェノン、4,4´−ジメチルベンゾフェノン、2−メチル−2´−メトキシベンゾフェノン、2−メチル−3´−メトキシベンゾフェノン、2−メチル−4´−メトキシベンゾフェノン、3−メチル−2´−メトキシベンゾフェノン、3−メチル−3´−メトキシベンゾフェノン、3−メチル−4´−メトキシベンゾフェノン、4−メチル−2´−メトキシベンゾフェノン、4−メチル−3´−メトキシベンゾフェノン、4−メチル−4´−メトキシベンゾフェノン、2−メチル−2´−フルオロベンゾフェノン、2−メチル−3´−フルオロベンゾフェノン、2−メチル−4´−フルオロベンゾフェノン、3−メチル−2´−フルオロベンゾフェノン、3−メチル−3´−フルオロベンゾフェノン、3−メチル−4´−フルオロベンゾフェノン、4−メチル−2´−フルオロベンゾフェノン、4−メチル−3´−フルオロベンゾフェノン、4−メチル−4´−フルオロベンゾフェノン、2−メチル−2´−クロロベンゾフェノン、2−メチル−3´−クロロベンゾフェノン、2−メチル−4´−クロロベンゾフェノン、3−メチル−2´−クロロベンゾフェノン、3−メチル−3´−クロロベンゾフェノン、3−メチル−4´−クロロベンゾフェノン、4−メチル−2´−クロロベンゾフェノン、4−メチル−3´−クロロベンゾフェノン、4−メチル−4´−クロロベンゾフェノン、2−メチル−2´−ブロモベンゾフェノン、2−メチル−3´−ブロモベンゾフェノン、2−メチル−4´−ブロモベンゾフェノン、3−メチル−2´−ブロモベンゾフェノン、3−メチル−3´−ブロモベンゾフェノン、3−メチル−4´−ブロモベンゾフェノン、4−メチル−2´−ブロモベンゾフェノン、4−メチル−3´−ブロモベンゾフェノン、4−メチル−4´−ブロモベンゾフェノン、2−メチル−2´−(トリフルオロメチル)ベンゾフェノン、2−メチル−3´−(トリフルオロメチル)ベンゾフェノン、2−メチル−4´−(トリフルオロメチル)ベンゾフェノン、3−メチル−2´−(トリフルオロメチル)ベンゾフェノン、3−メチル−3´−(トリフルオロメチル)ベンゾフェノン、3−メチル−4´−(トリフルオロメチル)ベンゾフェノン、4−メチル−2´−(トリフルオロメチル)ベンゾフェノン、4−メチル−3´−(トリフルオロメチル)ベンゾフェノン、4−メチル−4´−(トリフルオロメチル)ベンゾフェノン、2−メチル−2´−ジメチルアミノベンゾフェノン、2−メチル−3´−ジメチルアミノベンゾフェノン、2−メチル−4´−ジメチルアミノベンゾフェノン、3−メチル−3´−ジメチルアミノベンゾフェノン、3−メチル−4´−ジメチルアミノベンゾフェノン、4−メチル−4´−ジメチルアミノベンゾフェノン、2−メチル−2´−ニトロベンゾフェノン、2−メチル−3´−ニトロベンゾフェノン、2−メチル−4´−ニトロベンゾフェノン、3−メチル−2´−ニトロベンゾフェノン、3−メチル−3´−ニトロベンゾフェノン、3−メチル−4´−ニトロベンゾフェノン、4−メチル−2´−ニトロベンゾフェノン、4−メチル−3´−ニトロベンゾフェノン、4−メチル−4´−ニトロベンゾフェノン、2−メチルフェニル(2−ピリジル)ケトン、2−メチルフェニル(3−ピリジル)ケトン、2−メチルフェニル(4−ピリジル)ケトン、3−メチルフェニル(2−ピリジル)ケトン、3−メチルフェニル(3−ピリジル)ケトン、3−メチルフェニル(4−ピリジル)ケトン、4−メチルフェニル(2−ピリジル)ケトン、4−メチルフェニル(3−ピリジル)ケトン、4−メチルフェニル(4−ピリジル)ケトン、2−メチルフェニル(2−フリル)ケトン、2−メチルフェニル(3−フリル)ケトン、3−メチルフェニル(2−フリル)ケトン、3−メチルフェニル(3−フリル)ケトン、4−メチルフェニル(2−フリル)ケトン、4−メチルフェニル(3−フリル)ケトン、2−メチルフェニル(2−チエニル)ケトン、2−メチルフェニル(3−チエニル)ケトン、3−メチルフェニル(2−チエニル)ケトン、3−メチルフェニル(3−チエニル)ケトン、4−メチルフェニル(2−チエニル)ケトン、4−メチルフェニル(3−チエニル)ケトン、2−(2−メチルベンゾイル)ビフェニル、3−(2−メチルベンゾイル)ビフェニル、4−(2−メチルベンゾイル)ビフェニル、2−(3−メチルベンゾイル)ビフェニル、3−(3−メチルベンゾイル)ビフェニル、4−(3−メチルベンゾイル)ビフェニル、2−(4−メチルベンゾイル)ビフェニル、3−(4−メチルベンゾイル)ビフェニル、4−(4−メチルベンゾイル)ビフェニル、2´−メチルカルコン、3´−メチルカルコン、4´−メチルカルコン、2´−メチル−2−フルオロカルコン、2´−メチル−3−フルオロカルコン、2´−メチル−4−フルオロカルコン、3´−メチル−2−フルオロカルコン、3´−メチル−3−フルオロカルコン、3´−メチル−4−フルオロカルコン、4´−メチル−2−フルオロカルコン、4´−メチル−3−フルオロカルコン、4´−メチル−4−フルオロカルコン、2,2,2´−トリメチルプロピオフェノン、2,2,3´−トリメチルプロピオフェノン、2,2,4´−トリメチルプロピオフェノン等が挙げられる。 Specific examples of the carbonyl compounds represented by the general formula (1) applicable to the production of the present invention and in which R 1 and / or R 2 are a methyl phenyl group include 2-methylbenzaldehyde and 3-. Methylbenzaldehyde, 4-methylbenzaldehyde, 2,2'-dimethylbenzophenone, 2,3'-dimethylbenzophenone, 2,4'-dimethylbenzophenone, 3,3'-dimethylbenzophenone, 3,4'-dimethylbenzophenone, 4, 4'-dimethylbenzophenone, 2-methyl-2'-methoxybenzophenone, 2-methyl-3'-methoxybenzophenone, 2-methyl-4'-methoxybenzophenone, 3-methyl-2'-methoxybenzophenone, 3-methyl- 3'-methoxybenzophenone, 3-methyl-4'-methoxybenzophenone, 4-methyl-2'-methoxybenzophenone, 4-methyl-3'-methoxybenzophenone, 4-methyl-4'-methoxybenzophenone, 2-methyl- 2'-fluorobenzophenone, 2-methyl-3'-fluorobenzophenone, 2-methyl-4'-fluorobenzophenone, 3-methyl-2'-fluorobenzophenone, 3-methyl-3'-fluorobenzophenone, 3-methyl- 4'-fluorobenzophenone, 4-methyl-2'-fluorobenzophenone, 4-methyl-3'-fluorobenzophenone, 4-methyl-4'-fluorobenzophenone, 2-methyl-2'-chlorobenzophenone, 2-methyl- 3'-chlorobenzophenone, 2-methyl-4'-chlorobenzophenone, 3-methyl-2'-chlorobenzophenone, 3-methyl-3'-chlorobenzophenone, 3-methyl-4'-chlorobenzophenone, 4-methyl- 2'-chlorobenzophenone, 4-methyl-3'-chlorobenzophenone, 4-methyl-4'-chlorobenzophenone, 2-methyl-2'-bromobenzophenone, 2-methyl-3'-bromobenzophenone, 2-methyl- 4'-bromobenzophenone, 3-methyl-2'-bromobenzophenone, 3-methyl-3'-bromobenzophenone, 3-methyl-4'-bromobenzophenone, 4-methyl-2'-bromobenzophenone, 4-methyl- 3'-bromobenzophenone, 4-methyl-4'-bromobenzophenone, 2-methyl-2'-(trifluoromethyl) benzophenone, 2-methyl-3'-(trifluoro) Methyl) benzophenone, 2-methyl-4'-(trifluoromethyl) benzophenone, 3-methyl-2'-(trifluoromethyl) benzophenone, 3-methyl-3'-(trifluoromethyl) benzophenone, 3-methyl- 4'-(trifluoromethyl) benzophenone, 4-methyl-2'-(trifluoromethyl) benzophenone, 4-methyl-3'-(trifluoromethyl) benzophenone, 4-methyl-4'-(trifluoromethyl) Benzophenone, 2-methyl-2'-dimethylaminobenzophenone, 2-methyl-3'-dimethylaminobenzophenone, 2-methyl-4'-dimethylaminobenzophenone, 3-methyl-3'-dimethylaminobenzophenone, 3-methyl- 4'-dimethylaminobenzophenone, 4-methyl-4'-dimethylaminobenzophenone, 2-methyl-2'-nitrobenzophenone, 2-methyl-3'-nitrobenzophenone, 2-methyl-4'-nitrobenzophenone, 3- Methyl-2'-nitrobenzophenone, 3-methyl-3'-nitrobenzophenone, 3-methyl-4'-nitrobenzophenone, 4-methyl-2'-nitrobenzophenone, 4-methyl-3'-nitrobenzophenone, 4- Methyl-4'-nitrobenzophenone, 2-methylphenyl (2-pyridyl) ketone, 2-methylphenyl (3-pyridyl) ketone, 2-methylphenyl (4-pyridyl) ketone, 3-methylphenyl (2-pyridyl) Ketone, 3-methylphenyl (3-pyridyl) ketone, 3-methylphenyl (4-pyridyl) ketone, 4-methylphenyl (2-pyridyl) ketone, 4-methylphenyl (3-pyridyl) ketone, 4-methylphenyl (4-Pyridyl) ketone, 2-methylphenyl (2-furyl) ketone, 2-methylphenyl (3-furyl) ketone, 3-methylphenyl (2-furyl) ketone, 3-methylphenyl (3-furyl) ketone , 4-Methylphenyl (2-furyl) ketone, 4-methylphenyl (3-furyl) ketone, 2-methylphenyl (2-thienyl) ketone, 2-methylphenyl (3-thienyl) ketone, 3-methylphenyl ( 2-thienyl) ketone, 3-methylphenyl (3-thienyl) ketone, 4-methylphenyl (2-thienyl) ketone, 4-methylphenyl (3-thienyl) ketone, 2- (2-methylbenzophenone) biphenyl, 3 -(2-Methylbenzoyl ) Biphenyl, 4- (2-methylbenzoyl) biphenyl, 2- (3-methylbenzoyl) biphenyl, 3- (3-methylbenzoyl) biphenyl, 4- (3-methylbenzoyl) biphenyl, 2- (4-methylbenzoyl) ) Biphenyl, 3- (4-methylbenzoyl) biphenyl, 4- (4-methylbenzoyl) biphenyl, 2'-methyl chalcone, 3'-methyl chalcone, 4'-methyl chalcone, 2'-methyl-2-fluorochalcone , 2'-Methyl-3-fluorocarcon, 2'-methyl-4-fluorocarcon, 3'-methyl-2-fluorocarcon, 3'-methyl-3-fluorocarcon, 3'-methyl-4-fluorocarcon 4, 4'-Methyl-2-fluorocarcon, 4'-methyl-3-fluorocarcon, 4'-methyl-4-fluorocarcon, 2,2,2'-trimethylpropiophenone, 2,2,3'- Examples thereof include trimethylpropiophenone and 2,2,4'-trimethylpropiophenone.
本発明の製造に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1及び/又はR2がメトキシフェニル基である化合物としては、具体的には例えば、2−メトキシベンズアルデヒド、3−メトキシベンズアルデヒド、4−メトキシベンズアルデヒド、2,2´−ジメトキシベンゾフェノン、2,3´−ジメトキシベンゾフェノン、2,4´−ジメトキシベンゾフェノン、3,3´−ジメトキシベンゾフェノン、3,4´−ジメトキシベンゾフェノン、4,4´−ジメトキシベンゾフェノン、2−メトキシ−2´−フルオロベンゾフェノン、2−メトキシ−3´−フルオロベンゾフェノン、2−メトキシ−4´−フルオロベンゾフェノン、3−メトキシ−2´−フルオロベンゾフェノン、3−メトキシ−3´−フルオロベンゾフェノン、3−メトキシ−4´−フルオロベンゾフェノン、4−メトキシ−2´−フルオロベンゾフェノン、4−メトキシ−3´−フルオロベンゾフェノン、4−メトキシ−4´−フルオロベンゾフェノン、2−メトキシ−2´−クロロベンゾフェノン、2−メトキシ−3´−クロロベンゾフェノン、2−メトキシ−4´−クロロベンゾフェノン、3−メトキシ−2´−クロロベンゾフェノン、3−メトキシ−3´−クロロベンゾフェノン、3−メトキシ−4´−クロロベンゾフェノン、4−メトキシ−2´−クロロベンゾフェノン、4−メトキシ−3´−クロロベンゾフェノン、4−メトキシ−4´−クロロベンゾフェノン、2−メトキシ−2´−ブロモベンゾフェノン、2−メトキシ−3´−ブロモベンゾフェノン、2−メトキシ−4´−ブロモベンゾフェノン、3−メトキシ−2´−ブロモベンゾフェノン、3−メトキシ−3´−ブロモベンゾフェノン、3−メトキシ−4´−ブロモベンゾフェノン、4−メトキシ−2´−ブロモベンゾフェノン、4−メトキシ−3´−ブロモベンゾフェノン、4−メトキシ−4´−ブロモベンゾフェノン、2−メトキシ−2´−(トリフルオロメチル)ベンゾフェノン、2−メトキシ−3´−(トリフルオロメチル)ベンゾフェノン、2−メトキシ−4´−(トリフルオロメチル)ベンゾフェノン、3−メトキシ−2´−(トリフルオロメチル)ベンゾフェノン、3−メトキシ−3´−(トリフルオロメチル)ベンゾフェノン、3−メトキシ−4´−(トリフルオロメチル)ベンゾフェノン、4−メトキシ−2´−(トリフルオロメチル)ベンゾフェノン、4−メトキシ−3´−(トリフルオロメチル)ベンゾフェノン、4−メトキシ−4´−(トリフルオロメチル)ベンゾフェノン、2−メトキシ−2´−ジメチルアミノベンゾフェノン、2−メトキシ−3´−ジメチルアミノベンゾフェノン、2−メトキシ−4´−ジメチルアミノベンゾフェノン、3−メトキシ−3´−ジメチルアミノベンゾフェノン、3−メトキシ−4´−ジメチルアミノベンゾフェノン、4−メトキシ−4´−ジメチルアミノベンゾフェノン、2−メトキシ−2´−ニトロベンゾフェノン、2−メトキシ−3´−ニトロベンゾフェノン、2−メトキシ−4´−ニトロベンゾフェノン、3−メトキシ−2´−ニトロベンゾフェノン、3−メトキシ−3´−ニトロベンゾフェノン、3−メトキシ−4´−ニトロベンゾフェノン、4−メトキシ−2´−ニトロベンゾフェノン、4−メトキシ−3´−ニトロベンゾフェノン、4−メトキシ−4´−ニトロベンゾフェノン、2−メトキシフェニル(2−ピリジル)ケトン、2−メトキシフェニル(3−ピリジル)ケトン、2−メトキシフェニル(4−ピリジル)ケトン、3−メトキシフェニル(2−ピリジル)ケトン、3−メトキシフェニル(3−ピリジル)ケトン、3−メトキシフェニル(4−ピリジル)ケトン、4−メトキシフェニル(2−ピリジル)ケトン、4−メトキシフェニル(3−ピリジル)ケトン、4−メトキシフェニル(4−ピリジル)ケトン、2−メトキシフェニル(2−フリル)ケトン、2−メトキシフェニル(3−フリル)ケトン、3−メトキシフェニル(2−フリル)ケトン、3−メトキシフェニル(3−フリル)ケトン、4−メトキシフェニル(2−フリル)ケトン、4−メトキシフェニル(3−フリル)ケトン、2−メトキシフェニル(2−チエニル)ケトン、2−メトキシフェニル(3−チエニル)ケトン、3−メトキシフェニル(2−チエニル)ケトン、3−メトキシフェニル(3−チエニル)ケトン、4−メトキシフェニル(2−チエニル)ケトン、4−メトキシフェニル(3−チエニル)ケトン、2−(2−メトキシベンゾイル)ビフェニル、3−(2−メトキシベンゾイル)ビフェニル、4−(2−メトキシベンゾイル)ビフェニル、2−(3−メトキシベンゾイル)ビフェニル、3−(3−メトキシベンゾイル)ビフェニル、4−(3−メトキシベンゾイル)ビフェニル、2−(4−メトキシベンゾイル)ビフェニル、3−(4−メトキシベンゾイル)ビフェニル、4−(4−メトキシベンゾイル)ビフェニル、2´−メトキシカルコン、3´−メトキシカルコン、4´−メトキシカルコン、2´−メトキシ−2−フルオロカルコン、2´−メトキシ−3−フルオロカルコン、2´−メトキシ−4−フルオロカルコン、3´−メトキシ−2−フルオロカルコン、3´−メトキシ−3−フルオロカルコン、3´−メトキシ−4−フルオロカルコン、4´−メトキシ−2−フルオロカルコン、4´−メトキシ−3−フルオロカルコン、4´−メトキシ−4−フルオロカルコン、2,2−ジメチル−2´−メトキシプロピオフェノン、2,2−ジメチル−3´−メトキシプロピオフェノン、2,2−ジメチル−4´−メトキシプロピオフェノン等が挙げられる。 Specific examples of the carbonyl compounds represented by the general formula (1) applicable to the production of the present invention in which R 1 and / or R 2 are methoxyphenyl groups include, for example, 2-methoxybenzaldehyde, 3 -Methoxybenzaldehyde, 4-methoxybenzaldehyde, 2,2'-dimethoxybenzophenone, 2,3'-dimethoxybenzophenone, 2,4'-dimethoxybenzophenone, 3,3'-dimethoxybenzophenone, 3,4'-dimethoxybenzophenone, 4 , 4'-dimethoxybenzophenone, 2-methoxy-2'-fluorobenzophenone, 2-methoxy-3'-fluorobenzophenone, 2-methoxy-4'-fluorobenzophenone, 3-methoxy-2'-fluorobenzophenone, 3-methoxy -3'-fluorobenzophenone, 3-methoxy-4'-fluorobenzophenone, 4-methoxy-2'-fluorobenzophenone, 4-methoxy-3'-fluorobenzophenone, 4-methoxy-4'-fluorobenzophenone, 2-methoxy -2'-Chlorobenzophenone, 2-methoxy-3'-chlorobenzophenone, 2-methoxy-4'-chlorobenzophenone, 3-methoxy-2'-chlorobenzophenone, 3-methoxy-3'-chlorobenzophenone, 3-methoxy -4'-chlorobenzophenone, 4-methoxy-2'-chlorobenzophenone, 4-methoxy-3'-chlorobenzophenone, 4-methoxy-4'-chlorobenzophenone, 2-methoxy-2'-bromobenzophenone, 2-methoxy -3'-bromobenzophenone, 2-methoxy-4'-bromobenzophenone, 3-methoxy-2'-bromobenzophenone, 3-methoxy-3'-bromobenzophenone, 3-methoxy-4'-bromobenzophenone, 4-methoxy -2'-bromobenzophenone, 4-methoxy-3'-bromobenzophenone, 4-methoxy-4'-bromobenzophenone, 2-methoxy-2'-(trifluoromethyl) benzophenone, 2-methoxy-3'-(tri) Fluoromethyl) benzophenone, 2-methoxy-4'-(trifluoromethyl) benzophenone, 3-methoxy-2'-(trifluoromethyl) benzophenone, 3-methoxy-3'-(trifluoromethyl) benzophenone, 3-methoxy -4'-(trifluoromethyl) benzophenone, 4-methoxy-2'-(trifluoromethyl) Benzophenone, 4-methoxy-3'-(trifluoromethyl) benzophenone, 4-methoxy-4'-(trifluoromethyl) benzophenone, 2-methoxy-2'-dimethylaminobenzophenone, 2-methoxy-3'-dimethylamino Benzophenone, 2-methoxy-4'-dimethylaminobenzophenone, 3-methoxy-3'-dimethylaminobenzophenone, 3-methoxy-4'-dimethylaminobenzophenone, 4-methoxy-4'-dimethylaminobenzophenone, 2-methoxy- 2'-nitrobenzophenone, 2-methoxy-3'-nitrobenzophenone, 2-methoxy-4'-nitrobenzophenone, 3-methoxy-2'-nitrobenzophenone, 3-methoxy-3'-nitrobenzophenone, 3-methoxy- 4'-nitrobenzophenone, 4-methoxy-2'-nitrobenzophenone, 4-methoxy-3'-nitrobenzophenone, 4-methoxy-4'-nitrobenzophenone, 2-methoxyphenyl (2-pyridyl) ketone, 2-methoxy Phenyl (3-pyridyl) ketone, 2-methoxyphenyl (4-pyridyl) ketone, 3-methoxyphenyl (2-pyridyl) ketone, 3-methoxyphenyl (3-pyridyl) ketone, 3-methoxyphenyl (4-pyridyl) Ketone, 4-methoxyphenyl (2-pyridyl) ketone, 4-methoxyphenyl (3-pyridyl) ketone, 4-methoxyphenyl (4-pyridyl) ketone, 2-methoxyphenyl (2-furyl) ketone, 2-methoxyphenyl (3-Frill) Ketone, 3-methoxyphenyl (2-Frill) Ketone, 3-methoxyphenyl (3-Frill) Ketone, 4-methoxyphenyl (2-Frill) Ketone, 4-methoxyphenyl (3-Frill) Ketone , 2-methoxyphenyl (2-thienyl) ketone, 2-methoxyphenyl (3-thienyl) ketone, 3-methoxyphenyl (2-thienyl) ketone, 3-methoxyphenyl (3-thienyl) ketone, 4-methoxyphenyl ( 2-Thienyl Ketone, 4-methoxyphenyl (3-thienyl) Ketone, 2- (2-methoxybenzoyl) Biphenyl, 3- (2-methoxybenzoyl) Biphenyl, 4- (2-methoxybenzoyl) Biphenyl, 2- ( 3-methoxybenzoyl) biphenyl, 3- (3-methoxybenzoyl) biphenyl, 4- (3-methoxybenzoyl) biphenyl, 2- (4-methoxybenzoy) Le) Biphenyl, 3- (4-methoxybenzoyl) biphenyl, 4- (4-methoxybenzoyl) biphenyl, 2'-methoxycalcone, 3'-methoxycalcone, 4'-methoxycalcone, 2'-methoxy-2-fluoro Calcon, 2'-methoxy-3-fluorocarcon, 2'-methoxy-4-fluorocarcon, 3'-methoxy-2-fluorocarcon, 3'-methoxy-3-fluorocarcon, 3'-methoxy-4-fluoro Calcon, 4'-methoxy-2-fluorocarcon, 4'-methoxy-3-fluorocarcon, 4'-methoxy-4-fluorocarcon, 2,2-dimethyl-2'-methoxypropiophenone, 2,2- Examples thereof include dimethyl-3'-methoxypropiophenone and 2,2-dimethyl-4'-methoxypropiophenone.
本発明の製造に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1及び/又はR2がフルオロフェニル基である化合物としては、具体的には例えば、2−フルオロベンズアルデヒド、3−フルオロベンズアルデヒド、4−フルオロベンズアルデヒド、2,2´−ジフルオロベンゾフェノン、2,3´−ジフルオロベンゾフェノン、2,4´−ジフルオロベンゾフェノン、3,3´−ジフルオロベンゾフェノン、3,4´−ジフルオロベンゾフェノン、4,4´−ジフルオロベンゾフェノン、2−クロロ−2´−フルオロベンゾフェノン、3−クロロ−2´−フルオロベンゾフェノン、4−クロロ−2´−フルオロベンゾフェノン、2−クロロ−3´−フルオロベンゾフェノン、3−クロロ−3´−フルオロベンゾフェノン、4−クロロ−3´−フルオロベンゾフェノン、2−クロロ−4´−フルオロベンゾフェノン、3−クロロ−4´−フルオロベンゾフェノン、4−クロロ−4´−フルオロベンゾフェノン、2−ブロモ−2´−フルオロベンゾフェノン、3−ブロモ−2´−フルオロベンゾフェノン、4−ブロモ−2´−フルオロベンゾフェノン、2−ブロモ−3´−フルオロベンゾフェノン、3−ブロモ−3´−フルオロベンゾフェノン、4−ブロモ−3´−フルオロベンゾフェノン、2−ブロモ−4´−フルオロベンゾフェノン、3−ブロモ−4´−フルオロベンゾフェノン、4−ブロモ−4´−フルオロベンゾフェノン、2−(トリフルオロメチル)−2´−フルオロベンゾフェノン、3−(トリフルオロメチル)−2´−フルオロベンゾフェノン、4−(トリフルオロメチル)−2´−フルオロベンゾフェノン、2−(トリフルオロメチル)−3´−フルオロベンゾフェノン、3−(トリフルオロメチル)−3´−フルオロベンゾフェノン、4−(トリフルオロメチル)−3´−フルオロベンゾフェノン、2−(トリフルオロメチル)−4´−フルオロベンゾフェノン、3−(トリフルオロメチル)−4´−フルオロベンゾフェノン、4−(トリフルオロメチル)−4´−フルオロベンゾフェノン、2−フルオロ−2´−ジメチルアミノベンゾフェノン、2−フルオロ−3´−ジメチルアミノベンゾフェノン、2−フルオロ−4´−ジメチルアミノベンゾフェノン、3−フルオロ−3´−ジメチルアミノベンゾフェノン、3−フルオロ−4´−ジメチルアミノベンゾフェノン、4−フルオロ−4´−ジメチルアミノベンゾフェノン、2−フルオロ−2´−ニトロベンゾフェノン、2−フルオロ−3´−ニトロベンゾフェノン、2−フルオロ−4´−ニトロベンゾフェノン、3−フルオロ−2´−ニトロベンゾフェノン、3−フルオロ−3´−ニトロベンゾフェノン、3−フルオロ−4´−ニトロベンゾフェノン、4−フルオロ−2´−ニトロベンゾフェノン、4−フルオロ−3´−ニトロベンゾフェノン、4−フルオロ−4´−ニトロベンゾフェノン、2−フルオロフェニル(2−ピリジル)ケトン、2−フルオロフェニル(3−ピリジル)ケトン、2−フルオロフェニル(4−ピリジル)ケトン、3−フルオロフェニル(2−ピリジル)ケトン、3−フルオロフェニル(3−ピリジル)ケトン、3−フルオロフェニル(4−ピリジル)ケトン、4−フルオロフェニル(2−ピリジル)ケトン、4−フルオロフェニル(3−ピリジル)ケトン、4−フルオロフェニル(4−ピリジル)ケトン、2−フルオロフェニル(2−フリル)ケトン、2−フルオロフェニル(3−フリル)ケトン、3−フルオロフェニル(2−フリル)ケトン、3−フルオロフェニル(3−フリル)ケトン、4−フルオロフェニル(2−フリル)ケトン、4−フルオロフェニル(3−フリル)ケトン、2−フルオロフェニル(2−チエニル)ケトン、2−フルオロフェニル(3−チエニル)ケトン、3−フルオロフェニル(2−チエニル)ケトン、3−フルオロフェニル(3−チエニル)ケトン、4−フルオロフェニル(2−チエニル)ケトン、4−フルオロフェニル(3−チエニル)ケトン、2−(2−フルオロベンゾイル)ビフェニル、3−(2−フルオロベンゾイル)ビフェニル、4−(2−フルオロベンゾイル)ビフェニル、2−(3−フルオロベンゾイル)ビフェニル、3−(3−フルオロベンゾイル)ビフェニル、4−(3−フルオロベンゾイル)ビフェニル、2−(4−フルオロベンゾイル)ビフェニル、3−(4−フルオロベンゾイル)ビフェニル、4−(4−フルオロベンゾイル)ビフェニル、2´−フルオロカルコン、3´−フルオロカルコン、4´−フルオロカルコン、2,2´−ジフルオロカルコン、3,2´−ジフルオロカルコン、4,2´−ジフルオロカルコン、2,3´−ジフルオロカルコン、3,3´−ジフルオロカルコン、4,3´−ジフルオロカルコン、2,4´−ジフルオロカルコン、3,4´−ジフルオロカルコン、4,4´−ジフルオロカルコン、2,2−ジメチル−2´−フルオロプロピオフェノン、2,2−ジメチル−3´−フルオロプロピオフェノン、2,2−ジメチル−4´−フルオロプロピオフェノン等が挙げられる。 Specific examples of the carbonyl compounds represented by the general formula (1) applicable to the production of the present invention in which R 1 and / or R 2 are fluorophenyl groups include, for example, 2-fluorobenzaldehyde, 3 -Fluorobenzaldehyde, 4-fluorobenzaldehyde, 2,2'-difluorobenzophenone, 2,3'-difluorobenzophenone, 2,4'-difluorobenzophenone, 3,3'-difluorobenzophenone, 3,4'-difluorobenzophenone, 4 , 4'-difluorobenzophenone, 2-chloro-2'-fluorobenzophenone, 3-chloro-2'-fluorobenzophenone, 4-chloro-2'-fluorobenzophenone, 2-chloro-3'-fluorobenzophenone, 3-chloro -3'-fluorobenzophenone, 4-chloro-3'-fluorobenzophenone, 2-chloro-4'-fluorobenzophenone, 3-chloro-4'-fluorobenzophenone, 4-chloro-4'-fluorobenzophenone, 2-bromo -2'-Fluorobenzophenone, 3-bromo-2'-fluorobenzophenone, 4-bromo-2'-fluorobenzophenone, 2-bromo-3'-fluorobenzophenone, 3-bromo-3'-fluorobenzophenone, 4-bromo -3'-Fluorobenzophenone, 2-bromo-4'-fluorobenzophenone, 3-bromo-4'-fluorobenzophenone, 4-bromo-4'-fluorobenzophenone, 2- (trifluoromethyl) -2'-fluorobenzophenone , 3- (Trifluoromethyl) -2'-fluorobenzophenone, 4- (trifluoromethyl) -2'-fluorobenzophenone, 2- (trifluoromethyl) -3'-fluorobenzophenone, 3- (trifluoromethyl) -3'-Fluorobenzophenone, 4- (trifluoromethyl) -3'-fluorobenzophenone, 2- (trifluoromethyl) -4'-fluorobenzophenone, 3- (trifluoromethyl) -4'-fluorobenzophenone, 4 -(Trifluoromethyl) -4'-fluorobenzophenone, 2-fluoro-2'-dimethylaminobenzophenone, 2-fluoro-3'-dimethylaminobenzophenone, 2-fluoro-4'-dimethylaminobenzophenone, 3-fluoro- 3'-dimethylaminobenzophenone, 3-fluoro-4'-dimethylaminobenzophenone, 4-fluoro- 4'-Dimethylaminobenzophenone, 2-fluoro-2'-nitrobenzophenone, 2-fluoro-3'-nitrobenzophenone, 2-fluoro-4'-nitrobenzophenone, 3-fluoro-2'-nitrobenzophenone, 3-fluoro -3'-nitrobenzophenone, 3-fluoro-4'-nitrobenzophenone, 4-fluoro-2'-nitrobenzophenone, 4-fluoro-3'-nitrobenzophenone, 4-fluoro-4'-nitrobenzophenone, 2-fluoro Phenyl (2-pyridyl) ketone, 2-fluorophenyl (3-pyridyl) ketone, 2-fluorophenyl (4-pyridyl) ketone, 3-fluorophenyl (2-pyridyl) ketone, 3-fluorophenyl (3-pyridyl) Ketone, 3-fluorophenyl (4-pyridyl) ketone, 4-fluorophenyl (2-pyridyl) ketone, 4-fluorophenyl (3-pyridyl) ketone, 4-fluorophenyl (4-pyridyl) ketone, 2-fluorophenyl (2-Frill) Ketone, 2-Fluorophenyl (3-Frill) Ketone, 3-Fluorophenyl (2-Frill) Ketone, 3-Fluorophenyl (3-Frill) Ketone, 4-Fluorophenyl (2-Frill) Ketone , 4-Fluorophenyl (3-furyl) ketone, 2-fluorophenyl (2-thienyl) ketone, 2-fluorophenyl (3-thienyl) ketone, 3-fluorophenyl (2-thienyl) ketone, 3-fluorophenyl ( 3-thienyl) ketone, 4-fluorophenyl (2-thienyl) ketone, 4-fluorophenyl (3-thienyl) ketone, 2- (2-fluorobenzoyl) biphenyl, 3- (2-fluorobenzoyl) biphenyl, 4- (2-Fluorobenzoyl) biphenyl, 2- (3-fluorobenzoyl) biphenyl, 3- (3-fluorobenzoyl) biphenyl, 4- (3-fluorobenzoyl) biphenyl, 2- (4-fluorobenzoyl) biphenyl, 3- (4-Fluorobenzoyl) biphenyl, 4- (4-fluorobenzoyl) biphenyl, 2'-fluorocarcon, 3'-fluorocarcon, 4'-fluorocarcon, 2,2'-difluorocarcon, 3,2'-difluoro Calcon, 4,2'-difluorocarcon, 2,3'-difluorocarcon, 3,3'-difluorocarcon, 4,3'-difluorocarcon, 2,4'-difluorocarcon, 3,4'-diph Luolochalcone, 4,4'-difluorochalcone, 2,2-dimethyl-2'-fluoropropiophenone, 2,2-dimethyl-3'-fluoropropiophenone, 2,2-dimethyl-4'-fluoropropiophenone Examples include phenone.
本発明の製造に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1及び/又はR2がクロロフェニル基である化合物としては、具体的には例えば、2−クロロベンズアルデヒド、3−クロロベンズアルデヒド、4−クロロベンズアルデヒド、2,2´−ジクロロベンゾフェノン、2,3´−ジクロロベンゾフェノン、2,4´−ジクロロベンゾフェノン、3,3´−ジクロロベンゾフェノン、3,4´−ジクロロベンゾフェノン、4,4´−ジクロロベンゾフェノン、2−ブロモ−2´−クロロベンゾフェノン、3−ブロモ−2´−クロロベンゾフェノン、4−ブロモ−2´−クロロベンゾフェノン、2−ブロモ−3´−クロロベンゾフェノン、3−ブロモ−3´−クロロベンゾフェノン、4−ブロモ−3´−クロロベンゾフェノン、2−ブロモ−4´−クロロベンゾフェノン、3−ブロモ−4´−クロロベンゾフェノン、4−ブロモ−4´−クロロベンゾフェノン、2−(トリフルオロメチル)−2´−クロロベンゾフェノン、3−(トリフルオロメチル)−2´−クロロベンゾフェノン、4−(トリフルオロメチル)−2´−クロロベンゾフェノン、2−(トリフルオロメチル)−3´−クロロベンゾフェノン、3−(トリフルオロメチル)−3´−クロロベンゾフェノン、4−(トリフルオロメチル)−3´−クロロベンゾフェノン、2−(トリフルオロメチル)−4´−クロロベンゾフェノン、3−(トリフルオロメチル)−4´−クロロベンゾフェノン、4−(トリフルオロメチル)−4´−クロロベンゾフェノン、2−クロロ−2´−ジメチルアミノベンゾフェノン、2−クロロ−3´−ジメチルアミノベンゾフェノン、2−クロロ−4´−ジメチルアミノベンゾフェノン、3−クロロ−3´−ジメチルアミノベンゾフェノン、3−クロロ−4´−ジメチルアミノベンゾフェノン、4−クロロ−4´−ジメチルアミノベンゾフェノン、2−クロロ−2´−ニトロベンゾフェノン、2−クロロ−3´−ニトロベンゾフェノン、2−クロロ−4´−ニトロベンゾフェノン、3−クロロ−2´−ニトロベンゾフェノン、3−クロロ−3´−ニトロベンゾフェノン、3−クロロ−4´−ニトロベンゾフェノン、4−クロロ−2´−ニトロベンゾフェノン、4−クロロ−3´−ニトロベンゾフェノン、4−クロロ−4´−ニトロベンゾフェノン、2−クロロフェニル(2−ピリジル)ケトン、2−クロロフェニル(3−ピリジル)ケトン、2−クロロフェニル(4−ピリジル)ケトン、3−クロロフェニル(2−ピリジル)ケトン、3−クロロフェニル(3−ピリジル)ケトン、3−クロロフェニル(4−ピリジル)ケトン、4−クロロフェニル(2−ピリジル)ケトン、4−クロロフェニル(3−ピリジル)ケトン、4−クロロフェニル(4−ピリジル)ケトン、2−クロロフェニル(2−フリル)ケトン、2−クロロフェニル(3−フリル)ケトン、3−クロロフェニル(2−フリル)ケトン、3−クロロフェニル(3−フリル)ケトン、4−クロロフェニル(2−フリル)ケトン、4−クロロフェニル(3−フリル)ケトン、2−クロロフェニル(2−チエニル)ケトン、2−クロロフェニル(3−チエニル)ケトン、3−クロロフェニル(2−チエニル)ケトン、3−クロロフェニル(3−チエニル)ケトン、4−クロロフェニル(2−チエニル)ケトン、4−クロロフェニル(3−チエニル)ケトン、2−(2−クロロベンゾイル)ビフェニル、3−(2−クロロベンゾイル)ビフェニル、4−(2−クロロベンゾイル)ビフェニル、2−(3−クロロベンゾイル)ビフェニル、3−(3−クロロベンゾイル)ビフェニル、4−(3−クロロベンゾイル)ビフェニル、2−(4−クロロベンゾイル)ビフェニル、3−(4−クロロベンゾイル)ビフェニル、4−(4−クロロベンゾイル)ビフェニル、2´−クロロカルコン、3´−クロロカルコン、4´−クロロカルコン、2´−クロロ−2−フルオロカルコン、2´−クロロ−3−フルオロカルコン、2´−クロロ−4−フルオロカルコン、3´−クロロ−2−フルオロカルコン、3´−クロロ−3−フルオロカルコン、3´−クロロ−4−フルオロカルコン、4´−クロロ−2−フルオロカルコン、4´−クロロ−3−フルオロカルコン、4´−クロロ−4−フルオロカルコン、2,2−ジメチル−2´−クロロプロピオフェノン、2,2−ジメチル−3´−クロロプロピオフェノン、2,2−ジメチル−4´−クロロプロピオフェノン等が挙げられる。 Specific examples of the carbonyl compounds represented by the general formula (1) applicable to the production of the present invention in which R 1 and / or R 2 are chlorophenyl groups include 2-chlorobenzaldehyde and 3-. Chlorobenzaldehyde, 4-chlorobenzaldehyde, 2,2'-dichlorobenzophenone, 2,3'-dichlorobenzophenone, 2,4'-dichlorobenzophenone, 3,3'-dichlorobenzophenone, 3,4'-dichlorobenzophenone, 4, 4'-dichlorobenzophenone, 2-bromo-2'-chlorobenzophenone, 3-bromo-2'-chlorobenzophenone, 4-bromo-2'-chlorobenzophenone, 2-bromo-3'-chlorobenzophenone, 3-bromo- 3'-chlorobenzophenone, 4-bromo-3'-chlorobenzophenone, 2-bromo-4'-chlorobenzophenone, 3-bromo-4'-chlorobenzophenone, 4-bromo-4'-chlorobenzophenone, 2- (tri) Fluoromethyl) -2'-chlorobenzophenone, 3- (trifluoromethyl) -2'-chlorobenzophenone, 4- (trifluoromethyl) -2'-chlorobenzophenone, 2- (trifluoromethyl) -3'-chloro Benzophenone, 3- (trifluoromethyl) -3'-chlorobenzophenone, 4- (trifluoromethyl) -3'-chlorobenzophenone, 2- (trifluoromethyl) -4'-chlorobenzophenone, 3- (trifluoromethyl) ) -4'-Chlorobenzophenone, 4- (trifluoromethyl) -4'-chlorobenzophenone, 2-chloro-2'-dimethylaminobenzophenone, 2-chloro-3'-dimethylaminobenzophenone, 2-chloro-4' -Dimethylaminobenzophenone, 3-chloro-3'-dimethylaminobenzophenone, 3-chloro-4'-dimethylaminobenzophenone, 4-chloro-4'-dimethylaminobenzophenone, 2-chloro-2'-nitrobenzophenone, 2- Chloro-3'-nitrobenzophenone, 2-chloro-4'-nitrobenzophenone, 3-chloro-2'-nitrobenzophenone, 3-chloro-3'-nitrobenzophenone, 3-chloro-4'-nitrobenzophenone, 4- Chloro-2'-nitrobenzophenone, 4-chloro-3'-nitrobenzophenone, 4-chloro-4'-nitrobenzophenone, 2-chlorophenyl (2-pyridyl) ketone, 2-chromo Lophenyl (3-pyridyl) ketone, 2-chlorophenyl (4-pyridyl) ketone, 3-chlorophenyl (2-pyridyl) ketone, 3-chlorophenyl (3-pyridyl) ketone, 3-chlorophenyl (4-pyridyl) ketone, 4- Chlorophenyl (2-pyridyl) ketone, 4-chlorophenyl (3-pyridyl) ketone, 4-chlorophenyl (4-pyridyl) ketone, 2-chlorophenyl (2-furyl) ketone, 2-chlorophenyl (3-furyl) ketone, 3- Chlorophenyl (2-furyl) ketone, 3-chlorophenyl (3-furyl) ketone, 4-chlorophenyl (2-furyl) ketone, 4-chlorophenyl (3-furyl) ketone, 2-chlorophenyl (2-thienyl) ketone, 2- Chlorophenyl (3-thienyl) ketone, 3-chlorophenyl (2-thienyl) ketone, 3-chlorophenyl (3-thienyl) ketone, 4-chlorophenyl (2-thienyl) ketone, 4-chlorophenyl (3-thienyl) ketone, 2- (2-Chlorobenzoyl) biphenyl, 3- (2-chlorobenzoyl) biphenyl, 4- (2-chlorobenzoyl) biphenyl, 2- (3-chlorobenzoyl) biphenyl, 3- (3-chlorobenzoyl) biphenyl, 4- (3-Chlorobenzoyl) biphenyl, 2- (4-chlorobenzoyl) biphenyl, 3- (4-chlorobenzoyl) biphenyl, 4- (4-chlorobenzoyl) biphenyl, 2'-chlorochacon, 3'-chlorochacon, 4'-Chlorocalcon, 2'-Chloro-2-fluorochacon, 2'-Chloro-3-fluorocarcon, 2'-Chloro-4-fluorocarcon, 3'-Chloro-2-fluorocarcon, 3'-Chloro -3-Fluorocarcon, 3'-Chloro-4-fluorocarcon, 4'-Chloro-2-fluorocarcon, 4'-Chloro-3-fluorocarcon, 4'-Chloro-4-fluorocarcon, 2,2- Examples thereof include dimethyl-2'-chloropropiophenone, 2,2-dimethyl-3'-chloropropiophenone, 2,2-dimethyl-4'-chloropropiophenone and the like.
本発明の製造に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1及び/又はR2がブロモフェニル基である化合物としては、具体的には例えば、2−ブロモベンズアルデヒド、3−ブロモベンズアルデヒド、4−ブロモベンズアルデヒド、2,2´−ジブロモベンゾフェノン、2,3´−ジブロモベンゾフェノン、2,4´−ジブロモベンゾフェノン、3,3´−ジブロモベンゾフェノン、3,4´−ジブロモベンゾフェノン、4,4´−ジブロモベンゾフェノン、2−ブロモ−2´−(トリフルオロメチル)ベンゾフェノン、2−ブロモ−3´−(トリフルオロメチル)ベンゾフェノン、2−ブロモ−4´−(トリフルオロメチル)ベンゾフェノン、3−ブロモ−2´−(トリフルオロメチル)ベンゾフェノン、3−ブロモ−3´−(トリフルオロメチル)ベンゾフェノン、3−ブロモ−4´−(トリフルオロメチル)ベンゾフェノン、4−ブロモ−2´−(トリフルオロメチル)ベンゾフェノン、4−ブロモ−3´−(トリフルオロメチル)ベンゾフェノン、4−ブロモ−4´−(トリフルオロメチル)ベンゾフェノン、2−ブロモ−2´−ジメチルアミノベンゾフェノン、2−ブロモ−3´−ジメチルアミノベンゾフェノン、2−ブロモ−4´−ジメチルアミノベンゾフェノン、3−ブロモ−3´−ジメチルアミノベンゾフェノン、3−ブロモ−4´−ジメチルアミノベンゾフェノン、4−ブロモ−4´−ジメチルアミノベンゾフェノン、2−ブロモ−2´−ニトロベンゾフェノン、2−ブロモ−3´−ニトロベンゾフェノン、2−ブロモ−4´−ニトロベンゾフェノン、3−ブロモ−2´−ニトロベンゾフェノン、3−ブロモ−3´−ニトロベンゾフェノン、3−ブロモ−4´−ニトロベンゾフェノン、4−ブロモ−2´−ニトロベンゾフェノン、4−ブロモ−3´−ニトロベンゾフェノン、4−ブロモ−4´−ニトロベンゾフェノン、2−ブロモフェニル(2−ピリジル)ケトン、2−ブロモフェニル(3−ピリジル)ケトン、2−ブロモフェニル(4−ピリジル)ケトン、3−ブロモフェニル(2−ピリジル)ケトン、3−ブロモフェニル(3−ピリジル)ケトン、3−ブロモフェニル(4−ピリジル)ケトン、4−ブロモフェニル(2−ピリジル)ケトン、4−ブロモフェニル(3−ピリジル)ケトン、4−ブロモフェニル(4−ピリジル)ケトン、2−ブロモフェニル(2−フリル)ケトン、2−ブロモフェニル(3−フリル)ケトン、3−ブロモフェニル(2−フリル)ケトン、3−ブロモフェニル(3−フリル)ケトン、4−ブロモフェニル(2−フリル)ケトン、4−ブロモフェニル(3−フリル)ケトン、2−ブロモフェニル(2−チエニル)ケトン、2−ブロモフェニル(3−チエニル)ケトン、3−ブロモフェニル(2−チエニル)ケトン、3−ブロモフェニル(3−チエニル)ケトン、4−ブロモフェニル(2−チエニル)ケトン、4−ブロモフェニル(3−チエニル)ケトン、2−(2−ブロモベンゾイル)ビフェニル、3−(2−ブロモベンゾイル)ビフェニル、4−(2−ブロモベンゾイル)ビフェニル、2−(3−ブロモベンゾイル)ビフェニル、3−(3−ブロモベンゾイル)ビフェニル、4−(3−ブロモベンゾイル)ビフェニル、2−(4−ブロモベンゾイル)ビフェニル、3−(4−ブロモベンゾイル)ビフェニル、4−(4−ブロモベンゾイル)ビフェニル、2´−ブロモカルコン、3´−ブロモカルコン、4´−ブロモカルコン、2´−ブロモ−2−フルオロカルコン、2´−ブロモ−3−フルオロカルコン、2´−ブロモ−4−フルオロカルコン、3´−ブロモ−2−フルオロカルコン、3´−ブロモ−3−フルオロカルコン、3´−ブロモ−4−フルオロカルコン、4´−ブロモ−2−フルオロカルコン、4´−ブロモ−3−フルオロカルコン、4´−ブロモ−4−フルオロカルコン、2,2−ジメチル−2´−ブロモプロピオフェノン、2,2−ジメチル−3´−ブロモプロピオフェノン、2,2−ジメチル−4´−ブロモプロピオフェノン等が挙げられる。 Specific examples of the carbonyl compounds represented by the general formula (1) applicable to the production of the present invention in which R 1 and / or R 2 are a bromophenyl group include, for example, 2-bromobenzaldehyde, 3 -Bromobenzaldehyde, 4-bromobenzaldehyde, 2,2'-dibromobenzophenone, 2,3'-dibromobenzophenone, 2,4'-dibromobenzophenone, 3,3'-dibromobenzophenone, 3,4'-dibromobenzophenone, 4 , 4'-dibromobenzophenone, 2-bromo-2'-(trifluoromethyl) benzophenone, 2-bromo-3'-(trifluoromethyl) benzophenone, 2-bromo-4'-(trifluoromethyl) benzophenone, 3 -Bromo-2'-(trifluoromethyl) benzophenone, 3-bromo-3'-(trifluoromethyl) benzophenone, 3-bromo-4'-(trifluoromethyl) benzophenone, 4-bromo-2'-(trifluoromethyl) benzophenone Fluoromethyl) benzophenone, 4-bromo-3'-(trifluoromethyl) benzophenone, 4-bromo-4'-(trifluoromethyl) benzophenone, 2-bromo-2'-dimethylaminobenzophenone, 2-bromo-3' -Dimethylaminobenzophenone, 2-bromo-4'-dimethylaminobenzophenone, 3-bromo-3'-dimethylaminobenzophenone, 3-bromo-4'-dimethylaminobenzophenone, 4-bromo-4'-dimethylaminobenzophenone, 2 -Bromo-2'-nitrobenzophenone, 2-bromo-3'-nitrobenzophenone, 2-bromo-4'-nitrobenzophenone, 3-bromo-2'-nitrobenzophenone, 3-bromo-3'-nitrobenzophenone, 3 -Bromo-4'-nitrobenzophenone, 4-bromo-2'-nitrobenzophenone, 4-bromo-3'-nitrobenzophenone, 4-bromo-4'-nitrobenzophenone, 2-bromophenyl (2-pyridyl) ketone, 2-Bromophenyl (3-pyridyl) ketone, 2-bromophenyl (4-pyridyl) ketone, 3-bromophenyl (2-pyridyl) ketone, 3-bromophenyl (3-pyridyl) ketone, 3-bromophenyl (4) -Pyridyl) ketone, 4-bromophenyl (2-pyridyl) ketone, 4-bromophenyl (3-pyridyl) ketone, 4-bromophenyl (4-pyridyl) ketone, 2-bromophenyl (2-furyl) Ketone, 2-Bromophenyl (3-Frill) Ketone, 3-Bromophenyl (2-Frill) Ketone, 3-Bromophenyl (3-Frill) Ketone, 4-Bromophenyl (2-Frill) Ketone, 4-Bromophenyl (3-Frill) Ketone, 2-Bromophenyl (2-thienyl) Ketone, 2-Bromophenyl (3-thienyl) Ketone, 3-Bromophenyl (2-thienyl) Ketone, 3-Bromophenyl (3-thienyl) Ketone , 4-bromophenyl (2-thienyl) ketone, 4-bromophenyl (3-thienyl) ketone, 2- (2-bromobenzoyl) biphenyl, 3- (2-bromobenzoyl) biphenyl, 4- (2-bromobenzoyl) ) Biphenyl, 2- (3-bromobenzoyl) biphenyl, 3- (3-bromobenzoyl) biphenyl, 4- (3-bromobenzoyl) biphenyl, 2- (4-bromobenzoyl) biphenyl, 3- (4-bromobenzoyl) ) Biphenyl, 4- (4-bromobenzoyl) biphenyl, 2'-bromochalcone, 3'-bromochalcone, 4'-bromochalcone, 2'-bromo-2-fluorochacon, 2'-bromo-3-fluorocarcon , 2'-Bromo-4-fluorocarcon, 3'-Bromo-2-fluorocarcon, 3'-Bromo-3-fluorocarcon, 3'-Bromo-4-fluorocarcon, 4'-Bromo-2-fluorocarcon 4, 4'-Bromo-3-fluorochacon, 4'-bromo-4-fluorocarcon, 2,2-dimethyl-2'-bromopropiophenone, 2,2-dimethyl-3'-bromopropiophenone, 2 , 2-Dimethyl-4'-bromopropiophenone and the like.
本発明の製造に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1及び/又はR2が(トリフルオロメチル)フェニル基である化合物としては、具体的には例えば、2−(トリフルオロメチル)ベンズアルデヒド、3−(トリフルオロメチル)ベンズアルデヒド、4−(トリフルオロメチル)ベンズアルデヒド、2,2´−ビス(トリフルオロメチル)ベンゾフェノン、2,3´−ビス(トリフルオロメチル)ベンゾフェノン、2,4´−ビス(トリフルオロメチル)ベンゾフェノン、3,3´−ビス(トリフルオロメチル)ベンゾフェノン、3,4´−ビス(トリフルオロメチル)ベンゾフェノン、4,4´−ビス(トリフルオロメチル)ベンゾフェノン、2−(トリフルオロメチル)−2´−ジメチルアミノベンゾフェノン、2−(トリフルオロメチル)−3´−ジメチルアミノベンゾフェノン、2−(トリフルオロメチル)−4´−ジメチルアミノベンゾフェノン、3−(トリフルオロメチル)−3´−ジメチルアミノベンゾフェノン、3−(トリフルオロメチル)−4´−ジメチルアミノベンゾフェノン、4−(トリフルオロメチル)−4´−ジメチルアミノベンゾフェノン、2−(トリフルオロメチル)−2´−ニトロベンゾフェノン、2−(トリフルオロメチル)−3´−ニトロベンゾフェノン、2−(トリフルオロメチル)−4´−ニトロベンゾフェノン、3−(トリフルオロメチル)−2´−ニトロベンゾフェノン、3−(トリフルオロメチル)−3´−ニトロベンゾフェノン、3−(トリフルオロメチル)−4´−ニトロベンゾフェノン、4−(トリフルオロメチル)−2´−ニトロベンゾフェノン、4−(トリフルオロメチル)−3´−ニトロベンゾフェノン、4−(トリフルオロメチル)−4´−ニトロベンゾフェノン、2−(トリフルオロメチル)フェニル(2−ピリジル)ケトン、2−(トリフルオロメチル)フェニル(3−ピリジル)ケトン、2−(トリフルオロメチル)フェニル(4−ピリジル)ケトン、3−(トリフルオロメチル)フェニル(2−ピリジル)ケトン、3−(トリフルオロメチル)フェニル(3−ピリジル)ケトン、3−(トリフルオロメチル)フェニル(4−ピリジル)ケトン、4−(トリフルオロメチル)フェニル(2−ピリジル)ケトン、4−(トリフルオロメチル)フェニル(3−ピリジル)ケトン、4−(トリフルオロメチル)フェニル(4−ピリジル)ケトン、2−(トリフルオロメチル)フェニル(2−フリル)ケトン、2−(トリフルオロメチル)フェニル(3−フリル)ケトン、3−(トリフルオロメチル)フェニル(2−フリル)ケトン、3−(トリフルオロメチル)フェニル(3−フリル)ケトン、4−(トリフルオロメチル)フェニル(2−フリル)ケトン、4−(トリフルオロメチル)フェニル(3−フリル)ケトン、2−(トリフルオロメチル)フェニル(2−チエニル)ケトン、2−(トリフルオロメチル)フェニル(3−チエニル)ケトン、3−(トリフルオロメチル)フェニル(2−チエニル)ケトン、3−(トリフルオロメチル)フェニル(3−チエニル)ケトン、4−(トリフルオロメチル)フェニル(2−チエニル)ケトン、4−(トリフルオロメチル)フェニル(3−チエニル)ケトン、2−[2−(トリフルオロメチル)ベンゾイル]ビフェニル、3−[2−(トリフルオロメチル)ベンゾイル]ビフェニル、4−[2−(トリフルオロメチル)ベンゾイル]ビフェニル、2−[3−(トリフルオロメチル)ベンゾイル]ビフェニル、3−[3−(トリフルオロメチル)ベンゾイル]ビフェニル、4−[3−(トリフルオロメチル)ベンゾイル]ビフェニル、2−[4−(トリフルオロメチル)ベンゾイル]ビフェニル、3−[4−(トリフルオロメチル)ベンゾイル]ビフェニル、4−[4−(トリフルオロメチル)ベンゾイル]ビフェニル、2´−(トリフルオロメチル)カルコン、3´−(トリフルオロメチル)カルコン、4´−(トリフルオロメチル)カルコン、2´−(トリフルオロメチル)−2−フルオロカルコン、2´−(トリフルオロメチル)−3−フルオロカルコン、2´−(トリフルオロメチル)−4−フルオロカルコン、3´−(トリフルオロメチル)−2−フルオロカルコン、3´−(トリフルオロメチル)−3−フルオロカルコン、3´−(トリフルオロメチル)−4−フルオロカルコン、4´−(トリフルオロメチル)−2−フルオロカルコン、4´−(トリフルオロメチル)−3−フルオロカルコン、4´−(トリフルオロメチル)−4−フルオロカルコン、2,2−ジメチル−2´−(トリフルオロメチル)プロピオフェノン、2,2−ジメチル−3´−(トリフルオロメチル)プロピオフェノン、2,2−ジメチル−4´−(トリフルオロメチル)プロピオフェノン等が挙げられる。 Carbonyl compounds represented by the applicable general formula (1) in the preparation of the present invention, as the compound R 1 and / or R 2 is (trifluoromethyl) phenyl group, specifically, for example, 2- (Trifluoromethyl) benzaldehyde, 3- (trifluoromethyl) benzaldehyde, 4- (trifluoromethyl) benzaldehyde, 2,2'-bis (trifluoromethyl) benzophenone, 2,3'-bis (trifluoromethyl) benzophenone , 2,4'-bis (trifluoromethyl) benzophenone, 3,3'-bis (trifluoromethyl) benzophenone, 3,4'-bis (trifluoromethyl) benzophenone, 4,4'-bis (trifluoromethyl) ) Benzophenone, 2- (trifluoromethyl) -2'-dimethylaminobenzophenone, 2- (trifluoromethyl) -3'-dimethylaminobenzophenone, 2- (trifluoromethyl) -4'-dimethylaminobenzophenone, 3- (Trifluoromethyl) -3'-dimethylaminobenzophenone, 3- (trifluoromethyl) -4'-dimethylaminobenzophenone, 4- (trifluoromethyl) -4'-dimethylaminobenzophenone, 2- (trifluoromethyl) -2'-Nitrobenzophenone, 2- (trifluoromethyl) -3'-nitrobenzophenone, 2- (trifluoromethyl) -4'-nitrobenzophenone, 3- (trifluoromethyl) -2'-nitrobenzophenone, 3 -(Trifluoromethyl) -3'-nitrobenzophenone, 3- (trifluoromethyl) -4'-nitrobenzophenone, 4- (trifluoromethyl) -2'-nitrobenzophenone, 4- (trifluoromethyl) -3 ´-Nitrobenzophenone, 4- (trifluoromethyl) -4´-nitrobenzophenone, 2- (trifluoromethyl) phenyl (2-pyridyl) ketone, 2- (trifluoromethyl) phenyl (3-pyridyl) ketone, 2 -(Trifluoromethyl) phenyl (4-pyridyl) ketone, 3- (trifluoromethyl) phenyl (2-pyridyl) ketone, 3- (trifluoromethyl) phenyl (3-pyridyl) ketone, 3- (trifluoromethyl) ) Phenyl (4-pyridyl) ketone, 4- (trifluoromethyl) phenyl (2-pyridyl) ketone, 4- (trifluoromethyl) phenyl (3-pyridyl) ketone, 4- (trifluoromethyl) phenyl (4) -Pyridyl) ketone, 2- (trifluoromethyl) phenyl (2-furyl) ketone, 2- (trifluoromethyl) phenyl (3-furyl) ketone, 3- (trifluoromethyl) phenyl (2-furyl) ketone, 3- (Trifluoromethyl) phenyl (3-furyl) ketone, 4- (trifluoromethyl) phenyl (2-furyl) ketone, 4- (trifluoromethyl) phenyl (3-furyl) ketone, 2- (trifluoro) Methyl) phenyl (2-thienyl) ketone, 2- (trifluoromethyl) phenyl (3-thienyl) ketone, 3- (trifluoromethyl) phenyl (2-thienyl) ketone, 3- (trifluoromethyl) phenyl (3) -Thienyl) Ketone, 4- (Trifluoromethyl) phenyl (2-thienyl) Ketone, 4- (Trifluoromethyl) phenyl (3-thienyl) Ketone, 2- [2- (Trifluoromethyl) Benzoyl] Biphenyl, 3 -[2- (Trifluoromethyl) benzoyl] biphenyl, 4- [2- (trifluoromethyl) benzoyl] biphenyl, 2- [3- (trifluoromethyl) benzoyl] biphenyl, 3- [3- (trifluoromethyl) biphenyl ) Benzoyl] biphenyl, 4- [3- (trifluoromethyl) benzoyl] biphenyl, 2- [4- (trifluoromethyl) benzoyl] biphenyl, 3- [4- (trifluoromethyl) benzoyl] biphenyl, 4-[ 4- (Trifluoromethyl) benzoyl] biphenyl, 2'-(trifluoromethyl) chalcone, 3'-(trifluoromethyl) chalcone, 4'-(trifluoromethyl) chalcone, 2'-(trifluoromethyl)- 2-Fluorocarcon, 2'-(trifluoromethyl) -3-fluorocarcon, 2'-(trifluoromethyl) -4-fluorocarcon, 3'-(trifluoromethyl) -2-fluorocarcon, 3'- (Trifluoromethyl) -3-fluorochacon, 3'-(trifluoromethyl) -4-fluorocarcon, 4'-(trifluoromethyl) -2-fluorocarcon, 4'-(trifluoromethyl) -3- Fluorocalcone, 4'-(trifluoromethyl) -4-fluorocarcon, 2,2-dimethyl-2'-(trifluoromethyl) propiophenone, 2,2-dimethyl-3'-(trifluoromethyl) pro Piophenone, 2,2-dimethyl-4'-(trifluoromethyl) propiophenone and the like can be mentioned.
本発明の製造に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1及び/又はR2がニトロフェニル基である化合物としては、具体的には例えば、2−ニトロベンズアルデヒド、3−ニトロベンズアルデヒド、4−ニトロベンズアルデヒド、2,2´−ジニトロベンゾフェノン、2,3´−ジニトロベンゾフェノン、2,4´−ジニトロベンゾフェノン、3,3´−ジニトロベンゾフェノン、3,4´−ジニトロベンゾフェノン、4,4´−ジニトロベンゾフェノン、2−ニトロフェニル(2−ピリジル)ケトン、2−ニトロフェニル(3−ピリジル)ケトン、2−ニトロフェニル(4−ピリジル)ケトン、3−ニトロフェニル(2−ピリジル)ケトン、3−ニトロフェニル(3−ピリジル)ケトン、3−ニトロフェニル(4−ピリジル)ケトン、4−ニトロフェニル(2−ピリジル)ケトン、4−ニトロフェニル(3−ピリジル)ケトン、4−ニトロフェニル(4−ピリジル)ケトン、2−ニトロフェニル(2−フリル)ケトン、2−ニトロフェニル(3−フリル)ケトン、3−ニトロフェニル(2−フリル)ケトン、3−ニトロフェニル(3−フリル)ケトン、4−ニトロフェニル(2−フリル)ケトン、4−ニトロフェニル(3−フリル)ケトン、2−ニトロフェニル(2−チエニル)ケトン、2−ニトロフェニル(3−チエニル)ケトン、3−ニトロフェニル(2−チエニル)ケトン、3−ニトロフェニル(3−チエニル)ケトン、4−ニトロフェニル(2−チエニル)ケトン、4−ニトロフェニル(3−チエニル)ケトン、2−(2−ニトロベンゾイル)ビフェニル、3−(2−ニトロベンゾイル)ビフェニル、4−(2−ニトロベンゾイル)ビフェニル、2−(3−ニトロベンゾイル)ビフェニル、3−(3−ニトロベンゾイル)ビフェニル、4−(3−ニトロベンゾイル)ビフェニル、2−(4−ニトロベンゾイル)ビフェニル、3−(4−ニトロベンゾイル)ビフェニル、4−(4−ニトロベンゾイル)ビフェニル、2´−ニトロカルコン、3´−ニトロカルコン、4´−ニトロカルコン、2−フルオロ−2´−ニトロカルコン、3−フルオロ−2´−ニトロカルコン、4−フルオロ−2´−ニトロカルコン、2−フルオロ−3´−ニトロカルコン、3−フルオロ−3´−ニトロカルコン、4−フルオロ−3´−ニトロカルコン、2−フルオロ−4´−ニトロカルコン、3−フルオロ−4´−ニトロカルコン、4−フルオロ−4´−ニトロカルコン、2,2−ジメチル−2´−ニトロプロピオフェノン、2,2−ジメチル−3´−ニトロプロピオフェノン、2,2−ジメチル−4´−ニトロプロピオフェノン等が挙げられる。 Specific examples of the carbonyl compounds represented by the general formula (1) applicable to the production of the present invention, in which R 1 and / or R 2 are nitrophenyl groups, include, for example, 2-nitrobenzaldehyde, 3 -Nitrobenzaldehyde, 4-nitrobenzaldehyde, 2,2'-dinitrobenzophenone, 2,3'-dinitrobenzophenone, 2,4'-dinitrobenzophenone, 3,3'-dinitrobenzophenone, 3,4'-dinitrobenzophenone, 4 , 4'-Dinitrobenzophenone, 2-nitrophenyl (2-pyridyl) ketone, 2-nitrophenyl (3-pyridyl) ketone, 2-nitrophenyl (4-pyridyl) ketone, 3-nitrophenyl (2-pyridyl) ketone , 3-Nitrophenyl (3-pyridyl) ketone, 3-nitrophenyl (4-pyridyl) ketone, 4-nitrophenyl (2-pyridyl) ketone, 4-nitrophenyl (3-pyridyl) ketone, 4-nitrophenyl ( 4-Pyridyl) Ketone, 2-Nitrophenyl (2-Frill) Ketone, 2-Nitrophenyl (3-Frill) Ketone, 3-Nitrophenyl (2-Frill) Ketone, 3-Nitrophenyl (3-Frill) Ketone, 4-Nitrophenyl (2-furyl) ketone, 4-nitrophenyl (3-furyl) ketone, 2-nitrophenyl (2-thienyl) ketone, 2-nitrophenyl (3-thienyl) ketone, 3-nitrophenyl (2) -Thienyl) Ketone, 3-Nitrophenyl (3-Thienyl) Ketone, 4-Nitrophenyl (2-Thienyl) Ketone, 4-Nitrophenyl (3-Thienyl) Ketone, 2- (2-Nitrobenzoyl) Biphenyl, 3- (2-Nitrobenzoyl) biphenyl, 4- (2-nitrobenzoyl) biphenyl, 2- (3-nitrobenzoyl) biphenyl, 3- (3-nitrobenzoyl) biphenyl, 4- (3-nitrobenzoyl) biphenyl, 2- (4-Nitrobenzoyl) biphenyl, 3- (4-nitrobenzoyl) biphenyl, 4- (4-nitrobenzoyl) biphenyl, 2'-nitrochacon, 3'-nitrochacon, 4'-nitrochacon, 2-fluoro- 2'-Nitro Calcon, 3-Fluoro-2'-Nitro Calcon, 4-Fluoro-2'-Nitro Calcon, 2-Fluoro-3'-Nitro Calcon, 3-Fluoro-3'-Nitro Calcon, 4-Fluoro- 3'-Nitro Calcon, 2-Fluoro-4'-Nitro Calcon, 3-Fluoro- 4'-nitrochalcone, 4-fluoro-4'-nitrochalcone, 2,2-dimethyl-2'-nitropropiophenone, 2,2-dimethyl-3'-nitropropiophenone, 2,2-dimethyl- Examples thereof include 4'-nitropropiophenone.
本発明の製造に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1及び/又はR2がピリジル基である化合物としては、具体的には例えば、2−ホルミルピリジン、3−ホルミルピリジン、4−ホルミルピリジン、ジ(2−ピリジル)ケトン、2−ピリジル(3−ピリジル)ケトン、2−ピリジル(4−ピリジル)ケトン、ジ(3−ピリジル)ケトン、3−ピリジル(4−ピリジル)ケトン、4−ピリジル(3−ピリジル)ケトン、2−ピリジル(2−フリル)ケトン、2−ピリジル(3−フリル)ケトン、3−ピリジル(2−フリル)ケトン、3−ピリジル(3−フリル)ケトン、4−ピリジル(2−フリル)ケトン、4−ピリジル(3−フリル)ケトン、2−ピリジル(2−チエニル)ケトン、2−ピリジル(3−チエニル)ケトン、3ピリジル(2−チエニル)ケトン、3−ピリジル(3−チエニル)ケトン、4−ピリジル(2−チエニル)ケトン、4−ピリジル(3−チエニル)ケトン、2−ビフェニル(2−ピリジル)ケトン、3−ビフェニル(2−ピリジル)ケトン、4−ビフェニル(2−ピリジル)ケトン、2−ビフェニル(3−ピリジル)ケトン、3−ビフェニル(3−ピリジル)ケトン、4−ビフェニル(3−ピリジル)ケトン、2−ビフェニル(4−ピリジル)ケトン、3−ビフェニル(4−ピリジル)ケトン、4−ビフェニル(4−ピリジル)ケトン、スチリル(2−ピリジル)ケトン、スチリル(3−ピリジル)ケトン、スチリル(4−ピリジル)ケトン、2−フルオロスチリル(2−ピリジル)ケトン、3−フルオロスチリル(2−ピリジル)ケトン、4−フルオロスチリル(2−ピリジル)ケトン、2−フルオロスチリル(3−ピリジル)ケトン、3−フルオロスチリル(3−ピリジル)ケトン、4−フルオロスチリル(3−ピリジル)ケトン、2−フルオロスチリル(4−ピリジル)ケトン、3−フルオロスチリル(4−ピリジル)ケトン、4−フルオロスチリル(4−ピリジル)ケトン、2,2−ジメチル−1−(2-ピリジル)−1−プロパノン、2,2−ジメチル−1−(3−ピリジル)−1−プロパノン、2,2−ジメチル−1−(4−ピリジル)−1−プロパノン等が挙げられる。 Specific examples of the carbonyl compounds represented by the general formula (1) applicable to the production of the present invention in which R 1 and / or R 2 are pyridyl groups include 2-formylpyridine and 3-. Formyl pyridine, 4-formyl pyridine, di (2-pyridyl) ketone, 2-pyridyl (3-pyridyl) ketone, 2-pyridyl (4-pyridyl) ketone, di (3-pyridyl) ketone, 3-pyridyl (4-pyridyl) ketone Pyridyl) Ketone, 4-Pyridyl (3-Pyryl) Ketone, 2-Pyridyl (2-Frill) Ketone, 2-Pyridyl (3-Frill) Ketone, 3-Pyridyl (2-Frill) Ketone, 3-Pyridyl (3-Pyryl) Ketone Frill) Ketone, 4-Pyridyl (2-Frill) Ketone, 4-Pyryl (3-Frill) Ketone, 2-Pyridyl (2-Thienyl) Ketone, 2-Pyridyl (3-Thienyl) Ketone, 3-Pyridyl (2-Thienyl) Ketone ) Ketone, 3-pyridyl (3-thienyl) ketone, 4-pyridyl (2-thienyl) ketone, 4-pyridyl (3-thienyl) ketone, 2-biphenyl (2-pyridyl) ketone, 3-biphenyl (2-pyridyl) ) Ketone, 4-biphenyl (2-pyridyl) ketone, 2-biphenyl (3-pyridyl) ketone, 3-biphenyl (3-pyridyl) ketone, 4-biphenyl (3-pyridyl) ketone, 2-biphenyl (4-pyridyl) ) Ketone, 3-biphenyl (4-pyridyl) ketone, 4-biphenyl (4-pyridyl) ketone, styryl (2-pyridyl) ketone, styryl (3-pyridyl) ketone, styryl (4-pyridyl) ketone, 2-fluoro Styryl (2-pyridyl) ketone, 3-fluorostyryl (2-pyridyl) ketone, 4-fluorostyryl (2-pyridyl) ketone, 2-fluorostyryl (3-pyridyl) ketone, 3-fluorostyryl (3-pyridyl) Ketone, 4-fluorostyryl (3-pyridyl) ketone, 2-fluorostyryl (4-pyridyl) ketone, 3-fluorostyryl (4-pyridyl) ketone, 4-fluorostyryl (4-pyridyl) ketone, 2,2- Dimethyl-1- (2-pyridyl) -1-propanone, 2,2-dimethyl-1- (3-pyridyl) -1-propanone, 2,2-dimethyl-1- (4-pyridyl) -1-propanone, etc. Can be mentioned.
本発明の製造に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1及び/又はR2がビフェニル基である化合物としては、具体的には例えば、2−ホルミルビフェニル、3−ホルミルビフェニル、4−ホルミルビフェニル、4,4´−ジフェニルベンゾフェノン、スチリル(2−ビフェニル)ケトン、スチリル(3−ビフェニル)ケトン、スチリル(4−ビフェニル)ケトン、2−フルオロスチリル(2−ビフェニル)ケトン、3−フルオロスチリル(2−ビフェニル)ケトン、4−フルオロスチリル(2−ビフェニル)ケトン、2−フルオロスチリル(3−ビフェニル)ケトン、3−フルオロスチリル(3−ビフェニル)ケトン、4−フルオロスチリル(3−ビフェニル)ケトン、2−フルオロスチリル(4−ビフェニル)ケトン、3−フルオロスチリル(4−ビフェニル)ケトン、4−フルオロスチリル(4−ビフェニル)ケトン、2,2−ジメチル−1−(2-ビフェニル)−1−プロパノン、2,2−ジメチル−1−(3-ビフェニル)−1−プロパノン、2,2−ジメチル−1−(4-ビフェニル)−1−プロパノン等が挙げられる。 Specific examples of the carbonyl compounds represented by the general formula (1) applicable to the production of the present invention in which R 1 and / or R 2 are biphenyl groups include 2-formylbiphenyl and 3-. Formyl biphenyl, 4-formyl biphenyl, 4,4'-diphenylbenzophenone, styryl (2-biphenyl) ketone, styryl (3-biphenyl) ketone, styryl (4-biphenyl) ketone, 2-fluorostyryl (2-biphenyl) ketone , 3-Fluorostyryl (2-biphenyl) ketone, 4-fluorostyryl (2-biphenyl) ketone, 2-fluorostyryl (3-biphenyl) ketone, 3-fluorostyryl (3-biphenyl) ketone, 4-fluorostyryl ( 3-biphenyl) ketone, 2-fluorostyryl (4-biphenyl) ketone, 3-fluorostyryl (4-biphenyl) ketone, 4-fluorostyryl (4-biphenyl) ketone, 2,2-dimethyl-1- (2-) Biphenyl) -1-propanone, 2,2-dimethyl-1- (3-biphenyl) -1-propanone, 2,2-dimethyl-1- (4-biphenyl) -1-propanone and the like can be mentioned.
本発明の製造に適用可能な一般式(1)で表わされるカルボニル化合物類で、R1及びR2が結合して環を形成した化合物としては、具体的には例えば、9−フルオレノン、キサンテン−9−オン、9−アントラセンカルボキシアルデヒド等が挙げられる。 Specific examples of the carbonyl compounds represented by the general formula (1) applicable to the production of the present invention, in which R 1 and R 2 are bonded to form a ring, include 9-fluorenone and xanthene-. Examples thereof include 9-one and 9-anthracene carboxylaldehyde.
本発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及び/又はR2がフェニル基である化合物としては、具体的には例えば、2,2,3,3,3−ペンタフルオロ−1−フェニルプロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ジフェニルプロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−[2−(ペンタフルオロ−メチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−[3−(ペンタフルオロ−メチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−[4−(ペンタフルオロ−メチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−ジメチルアミノフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−ジメチルアミノフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−ジメチルアミノフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−ビフェニル)プロパノール、4,4,5,5,5−ペンタフルオロ−1,3−ジフェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−1−(2−フルオロフェニル)−3−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−1−(3−フルオロフェニル)−3−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−1−(4−フルオロフェニル)−3−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−フェニル−3−ペンタノール等が挙げられる。 Specific examples of the pentafluoroethyl group-containing alcohols represented by the general formula (2) produced in the production of the present invention, in which R 1 and / or R 2 are phenyl groups, are, for example, 2,2. 3,3,3-Pentafluoro-1-phenylpropanol, 2,2,3,3,3-pentafluoro-1,1-diphenylpropanol, 2,2,3,3,3-pentafluoro-1-phenyl -1- (2-Methylphenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (3-methylphenyl) propanol, 2,2,3,3,3-pentafluoro -1-Phenyl-1- (4-methylphenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (2-methoxyphenyl) propanol, 2,2,3,3 3-Phenylfluoro-1-phenyl-1- (3-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (4-methoxyphenyl) propanol, 2,2 3,3,3-Phenylfluoro-1-phenyl-1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (2-chlorophenyl) ) Propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (4) -Chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (2-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1 -(3-Bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1 -Phenyl-1- [2- (pentafluoro-methyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- [3- (pentafluoro-methyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- [4- (pentafluoro-methyl) phenyl] propanol, 2,2,3,3 3-Phenylfluoro-1-phenyl-1- (2-dimethylaminophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (3-dimethylaminophenyl) propanol, 2, 2,3,3,3-Phenylfluoro-1-phenyl-1- (4-dimethylaminophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (2-nitrophenyl) ) Phenyl, 2,2,3,3,3-pentafluoro-1-phenyl-1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1-( 4-Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl- 1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- Phenyl-1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro- 1-Phenyl-1- (4-furyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (2-thienyl) propanol, 2,2,3,3,3-penta Fluoro-1-phenyl-1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (4-thienyl) propanol, 2,2,3,3,3 -Pentafluoro-1-phenyl-1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (3-biphenyl) propanol, 2,2,3,3 , 3-Phenyl-1-phenyl-1- (4-biphenyl) propanol, 4,4,5,5,5-pentafluoro-1,3-diphenyl-1-buten-3-ol, 4,4 5,5,5-Pentafluoro-1- (2-fluorophenyl) -3-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-1- (3-fluorophenyl) ) -3-Phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-1- (4-fluorophenyl) -3-phenyl-1-buten-3-ol, 4, 4,5,5,5-pentafluoro-2,2-dimethyl Examples thereof include -3-phenyl-3-pentanol.
本発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及び/又はR2がメチルフェニル基である化合物としては、具体的には例えば、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(2−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(3−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(4−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(3−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(4−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(4−メチルフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(2−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(3−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(4−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(2−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(3−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(4−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(2−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(3−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(4−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルメチルフェニル)−1−(2−アミノフェニル)プロパノール、
2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルメチルフェニル)−1−(3−ジメチルアミノフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(4−ジメチルアミノフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−メチルフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−メチルフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−メチルフェニル)−1−(4−ビフェニル)プロパノール、4,4,5,5,5−ペンタフルオロ−3−(2−メチルフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−メチルフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−メチルフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−フルオロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−メチルフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−メチルフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−メチルフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−メチルフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−メチルフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−メチルフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−メチルフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−メチルフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(2−メチルフェニル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(3−メチルフェニル)−3−ブタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(4−メチルフェニル)−3−ブタノール等が挙げられる。
Specific examples of the pentafluoroethyl group-containing alcohols represented by the general formula (2) produced in the production of the present invention in which R 1 and / or R 2 are methylphenyl groups include 2,2. , 3,3,3-Pentafluoro-1- (2-methylphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- (4-methylphenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (2-methylphenyl) propanol, 2,2,3,3 3-Pentafluoro-1- (2-methylphenyl) -1- (3-methylphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (4) -Methylphenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (3-methylphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-) Methylphenyl) -1- (4-methylphenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (4-methylphenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (2-methylphenyl) -1- (2-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (3-methoxy) Phenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (4-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro-1 -(3-Methylphenyl) -1- (2-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (3-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (4-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-) Methylphenyl) -1- (2-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (3-methoxyphenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (4-methylphenyl) -1- (4-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl)- 1- (2-fluorophenyl) Nyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1 -(2-Methylphenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-) Methylphenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (2-fluorophenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (4-methylphenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl)- 1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (2-chlorophenyl) propanol, 2,2,3,3,3 -Pentafluoro-1- (2-methylphenyl) -1- (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (4-chlorophenyl) ) Propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- ( 3-Methylphenyl) -1- (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (4-chlorophenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (4-methylphenyl) -1- (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1 -(3-Chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (4-chlorophenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (2-methylphenyl) -1- (2-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (3-bromophenyl) ) Phenyl Ropanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1-( 3-Methylphenyl) -1- (2-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (3-bromophenyl) propanol, 2, 2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) ) -1- (2-Bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (3-bromophenyl) propanol, 2,2,3 3,3-Pentafluoro-1- (4-methylphenyl) -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- [2- (Trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- [3- (trifluoromethyl) phenyl] propanol, 2, 2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- [4- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1-( 3-Methylphenyl) -1- [2- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- [3- (trifluoro) Methyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- [4- (trifluoromethyl) phenyl] propanol, 2,2,3,3 3-Pentafluoro-1- (4-methylphenyl) -1- [2- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl)- 1- [3- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- [4- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (2-dimethylmethylphenyl) -1- (2-aminophenyl) propanol,
2,2,3,3,3-pentafluoro-1- (2-dimethylmethylphenyl) -1- (3-dimethylaminophenyl) propanol, 2,2,3,3,3-pentafluoro-1-( 2-Methylphenyl) -1- (4-dimethylaminophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (2-nitrophenyl) propanol, 2 , 2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methyl) Phenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (2-nitrophenyl) propanol, 2,2,3 , 3,3-Pentafluoro-1- (3-methylphenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1 -(4-Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3 -Pentafluoro-1- (4-methylphenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (4-) Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1 -(2-Methylphenyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (4-pyridyl) propanol, 2, 2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (3-Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3 -Pentafluoro-1- (4-methylphenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (3-pyridyl) ) Phenyl, 2,2,3,3,3-pentafluoro-1- (4-me) Tylphenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (2-furyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- (2-methylphenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (2) -Frill) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro-1 -(4-Methylphenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (3-furyl) propanol, 2, 2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (2-thienyl) propanol, 2,2,3,3,3 -Pentafluoro-1- (3-methylphenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (2-thienyl) ) Propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- ( 2-Methylphenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-methylphenyl) -1- (3-biphenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (2-methylphenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1 -(2-Biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-methylphenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (3-methylphenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (2-biphenyl) propanol , 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (3-biphenyl) Propanol, 2,2,3,3,3-pentafluoro-1- (4-methylphenyl) -1- (4-biphenyl) propanol, 4,4,5,5,5-pentafluoro-3- (2) -Methylphenyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-methylphenyl) -1-phenyl-1-buten-3-ol , 4,4,5,5,5-pentafluoro-3- (4-methylphenyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3-3 (2-Fluorophenyl) -1- (2-Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (2-methylphenyl) -1- (3) -Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (2-methylphenyl) -1- (4-fluorophenyl) -1-buten-3-3 All, 4,4,5,5,5-pentafluoro-3- (3-methylphenyl) -1- (2-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5 -Pentafluoro-3- (3-methylphenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-methylphenyl) ) -1- (4-Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-methylphenyl) -1- (2-fluorophenyl)- 1-Buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-methylphenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4 , 5,5,5-pentafluoro-3- (4-methylphenyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-2 , 2-Dimethyl-3- (2-methylphenyl) -3-pentanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (3-methylphenyl) -3-butanol , 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (4-methylphenyl) -3-butanol and the like.
発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及び/又はR2がメトキシフェニル基である化合物としては、具体的には例えば、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1,1−ビス(2−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(3−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(4−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1,1−ビス(3−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(4−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1,1−ビス(4−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−ジメチルアミノフェニル)−1−(2−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−ジメチルアミノフェニル)−1−(2−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−ジメチルアミノフェニル)−1−(2−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−ジメチルアミノフェニル)−1−(3−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−ジメチルアミノフェニル)−1−(3−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−ジメチルアミノフェニル)−1−(3−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−ジメチルアミノフェニル)−1−(4−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−ジメチルアミノフェニル)−1−(4−メトキシフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−ジメチルアミノフェニル)−1−(4−メトキシフェニル)プロパノール、
2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(2−メトキシフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(3−メトキシフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ1−(4−メトキシフェニル)−1−(4−ビフェニル)プロパノール、4,4,5,5,5−ペンタフルオロ−3−(2−メトキシフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−メトキシフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−メトキシフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−フルオロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−メトキシフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−メトキシフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−メトキシフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−メトキシフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−メトキシフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−メトキシフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−メトキシフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−メトキシフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(2−メトキシフェニル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(3−メトキシフェニル)−3−ブタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(4−メトキシフェニル)−3−ブタノール等が挙げられる。
Specific examples of the pentafluoroethyl group-containing alcohols represented by the general formula (2) produced in the production of the present invention and in which R 1 and / or R 2 are methoxyphenyl groups include 2,2. 3,3,3-Pentafluoro1- (2-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) propanol, 2,2,3,3-3 Pentafluoro1- (4-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1,1-bis (2-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1 -(2-methoxyphenyl) -1- (3-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (4-methoxyphenyl) propanol, 2 , 2,3,3,3-pentafluoro1,1-bis (3-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (4-) Phenyl) propanol, 2,2,3,3,3-pentafluoro1,1-bis (4-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (2-Fluorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3 3-Pentafluoro1- (2-methoxyphenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (2-fluoro) Phenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro1-( 3-methoxyphenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (2-fluorophenyl) propanol, 2,2 , 3,3,3-Pentafluoro1- (4-methoxyphenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1 -(4-Fluorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (2-chloro Phenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (2) -Methenylphenyl) -1- (4-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (2-chlorophenyl) propanol, 2,2,3 3,3-Pentafluoro1- (3-methoxyphenyl) -1- (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (4-) Chlorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (4) −methoxyphenyl) -1- (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (4-chlorophenyl) propanol, 2,2,3 3,3-Pentafluoro1- (2-methoxyphenyl) -1- (2-bromophenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (3) -Bromophenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro1 -(3-methoxyphenyl) -1- (2-bromophenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (3-bromophenyl) propanol, 2 , 2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (2-Bromophenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (3-bromophenyl) propanol, 2,2,3,3 3-Pentafluoro1- (4-methoxyphenyl) -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- [2-( Trifluoromethyl) Phenyl] propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- [3- (trifluoro) Methyl) phenyl] propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- [4- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3 -Pentafluoro1- (3-methoxyphenyl) -1- [2- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- [ 3- (Trifluoromethyl) Phenyl] Phenyl, 2,2,3,3,3-Pentafluoro1- (3-methoxyphenyl) -1- [4- (Trifluoromethyl) Phenyl] Phenyl, 2,2 3,3,3-Pentafluoro1- (4-methoxyphenyl) -1- [2- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) ) -1- [3- (Trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- [4- (trifluoromethyl) phenyl] propanol , 2,2,3,3,3-pentafluoro1- (2-dimethylaminophenyl) -1- (2-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-) Dimethylaminophenyl) -1- (2-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-dimethylaminophenyl) -1- (2-methoxyphenyl) propanol, 2,2 , 3,3,3-Pentafluoro1- (2-dimethylaminophenyl) -1- (3-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-dimethylaminophenyl) -1- (3-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-dimethylaminophenyl) -1- (3-methoxyphenyl) propanol, 2,2,3,3 , 3-Pentafluoro1- (2-dimethylaminophenyl) -1- (4-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-dimethylaminophenyl) -1-( 4-methoxyphenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-dimethylaminophenyl) -1- (4-methoxyphenyl) propanol,
2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) ) -1- (3-Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3 , 3-Pentafluoro1- (3-methoxyphenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (3-) Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (3-nitrophenyl) propanol, 2, 2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl)- 1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-penta Fluoro1- (2-methoxyphenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (2-pyridyl) propanol, 2 , 2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl)- 1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3-penta Fluoro1- (4-methoxyphenyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (4-pyridyl) propanol, 2 , 2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl)- 1- (3-Frill) Pro Panol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxy) Phenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (2-furyl) propanol, 2,2,3,3 3-Pentafluoro1- (4-methoxyphenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (2-thienyl) Propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxy) Phenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (3-thienyl) propanol, 2,2,3,3 3-Pentafluoro1- (4-methoxyphenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (3-thienyl) Propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxy) Phenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro1- (2-methoxyphenyl) -1- (4-biphenyl) propanol, 2,2,3,3 3-Pentafluoro1- (3-methoxyphenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (3-biphenyl) Propanol, 2,2,3,3,3-pentafluoro1- (3-methoxyphenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxy) Phenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro1- (4-methoxyphenyl) -1- (3-biphenyl) propanol, 2,2,3,3 3-Pentafluoro1- (4-methoxyphenyl) -1- (4-biphenyl) propanol, 4,4,5,5,5-pentafluoro-3- (2-methoxyphenyl) -1-phenyl-1- Buten-3-all, 4,4,5,5 , 5-Phenylfluoro-3- (3-methoxyphenyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-methoxyphenyl) -1 −Phenyl-1-butene-3-ol, 4,4,5,5,5-pentafluoro-3- (2-fluorophenyl) -1- (2-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (2-methoxyphenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-penta Fluoro-3- (2-methoxyphenyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-methoxyphenyl)- 1- (2-Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-methoxyphenyl) -1- (3-fluorophenyl) -1- Buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-methoxyphenyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5 , 5,5-Pentafluoro-3- (4-methoxyphenyl) -1- (2-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3-( 4-methoxyphenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-methoxyphenyl) -1- (4-) Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (2-methoxyphenyl) -3-pentanol, 4,4,5 , 5,5-pentafluoro-2,2-dimethyl-3- (3-methoxyphenyl) -3-butanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (4) −methoxyphenyl) -3-butanol and the like.
本発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及び/又はR2がフルオロフェニル基である化合物としては、具体的には例えば、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(2−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(3−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(4−フルオロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(4−ニトロフェニル)プロパノール、
2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−フルオロフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−フルオロフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−(4−ビフェニル)プロパノール、4,4,5,5,5−ペンタフルオロ−3−(2−フルオロフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−フルオロフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−フルオロフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−フルオロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−フルオロフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−フルオロフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−フルオロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−フルオロフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−フルオロフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−フルオロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−フルオロフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−フルオロフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(2−フルオロフェニル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(3−フルオロフェニル)−3−ブタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(4−フルオロフェニル)−3−ブタノール等が挙げられる。
Specific examples of the pentafluoroethyl group-containing alcohols represented by the general formula (2) produced in the production of the present invention and in which R 1 and / or R 2 are a fluorophenyl group include 2, 2 , 3,3,3-Pentafluoro-1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-fluorophenyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (2-fluorophenyl) propanol, 2,2,3,3 3-Pentafluoro-1- (2-fluorophenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-fluorophenyl) -1- (4) -Fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-fluorophenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro -1- (3-Fluorophenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (4-fluorophenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (2-chlorophenyl) -1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (2-Fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (2-fluorophenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (2-chlorophenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (3-fluorophenyl) propanol , 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-) Chlorophenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (4-fluorophenyl) propanol, 2,2,3 3,3-Pentafluoro-1- (4-chlorophenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1 -(2-Bromophenyl) -1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-bromophenyl) -1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-) Bromophenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (3-fluorophenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (4-bromophenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-bromophenyl)- 1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3 3-Pentafluoro-1- (4-bromophenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl]- 1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (2-fluorophenyl) propanol, 2,2 3,3,3-Pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2-] (Trifluoromethyl) phenyl] -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (3-fluoro) Phenyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (3-fluorophenyl) propanol, 2,2,3,3-3 Pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl ] -1- (4-Fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (4-fluorophenyl) Propanol, 2,2,3,3,3-pentafluoro-1- (2-dimethylaminophenyl) -1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-Dimethylaminophenyl) -1- (2-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (2-fluorophenyl) propanol , 2,2,3,3,3-pentafluoro-1- (2-dimethylaminophenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1-( 3-Dimethylaminophenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (3-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-dimethylaminophenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3) -Dimethylaminophenyl) -1- (4-fluorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (4-fluorophenyl) propanol, 2 , 2,3,3,3-pentafluoro-1- (2-fluorophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-fluoro) Phenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-fluorophenyl) -1- (4-nitrophenyl) propanol, 2,2,3 , 3,3-Pentafluoro-1- (3-fluorophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-fluorophenyl) -1 -(3-Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-fluorophenyl) -1- (4-nitrophenyl) propanol,
2,2,3,3,3-pentafluoro-1- (4-fluorophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-) Fluorophenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-fluorophenyl) -1- (4-nitrophenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (2-fluorophenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-fluorophenyl) -1 -(3-Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-fluorophenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-penta Fluoro-1- (3-fluorophenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-fluorophenyl) -1- (3-pyridyl) propanol , 2,2,3,3,3-pentafluoro-1- (3-fluorophenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-) Fluorophenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-fluorophenyl) -1- (3-pyridyl) propanol, 2,2,3 3,3-Pentafluoro-1- (4-fluorophenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-fluorophenyl) -1-( 2-Frill) propanol, 2,2,3,3,3-pentafluoro-1- (2-fluorophenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro- 1- (3-Fluorophenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-fluorophenyl) -1- (3-furyl) propanol, 2 , 2,3,3,3-pentafluoro-1- (4-fluorophenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-fluorophenyl) ) -1- (3-Frill) propanol, 2,2,3,3,3-pentafluoro-1- (2-fluorophenyl) -1- (2-thienyl) propanol, 2,2,3,3 3-Pentafluoro-1- (2-fluorophenyl) -1- (3-thienyl) propano , 2,2,3,3,3-pentafluoro-1- (3-fluorophenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- ( 3-Fluorophenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-fluorophenyl) -1- (2-thienyl) propanol, 2,2 3,3,3-Pentafluoro-1- (4-fluorophenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-fluorophenyl) -1 -(2-Biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-fluorophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (2-fluorophenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-fluorophenyl) -1- (2-biphenyl) propanol , 2,2,3,3,3-pentafluoro-1- (3-fluorophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-) Fluorophenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-fluorophenyl) -1- (2-biphenyl) propanol, 2,2,3 3,3-Pentafluoro-1- (4-fluorophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-fluorophenyl) -1-( 4-Biphenyl) propanol, 4,4,5,5,5-pentafluoro-3- (2-fluorophenyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5- Pentafluoro-3- (3-fluorophenyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-fluorophenyl) -1-phenyl- 1-Buten-3-ol, 4,4,5,5,5-pentafluoro-3- (2-fluorophenyl) -1- (2-fluorophenyl) -1-buten-3-ol, 4,4 , 5,5,5-pentafluoro-3- (2-fluorophenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3 -(2-Fluorophenyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4, 4,5,5,5-pentafluoro-3- (3-fluorophenyl) -1- (2-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro- 3- (3-Fluorophenyl) -1- (3-Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-fluorophenyl) -1- (4-Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-fluorophenyl) -1- (2-fluorophenyl) -1-buten- 3-ol, 4,4,5,5,5-pentafluoro-3- (4-fluorophenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5 , 5-Pentafluoro-3- (4-fluorophenyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-2,2-dimethyl -3- (2-Fluorophenyl) -3-pentanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (3-fluorophenyl) -3-butanol, 4,4 , 5,5,5-pentafluoro-2,2-dimethyl-3- (4-fluorophenyl) -3-butanol and the like.
本発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及び/又はR2がクロロフェニル基である化合物としては、具体的には例えば、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(2−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(3−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(4−クロロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(3−フリル)プロパノール、
2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−クロロフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−クロロフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(32−クロロフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−クロロフェニル)−1−(4−ビフェニル)プロパノール、4,4,5,5,5−ペンタフルオロ−3−(2−クロロフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−クロロフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−クロロフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−クロロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−クロロフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−クロロフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−クロロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−クロロフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−クロロフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−クロロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−クロロフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−クロロフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(2−クロロフェニル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(3−クロロフェニル)−3−ブタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(4−クロロフェニル)−3−ブタノール等が挙げられる。
Specific examples of the pentafluoroethyl group-containing alcohols represented by the general formula (2) produced in the production of the present invention and compounds in which R 1 and / or R 2 are chlorophenyl groups include 2,2. 3,3,3-Pentafluoro-1- (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (4-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro- 1- (2-chlorophenyl) -1- (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (4-chlorophenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1,1-bis (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (4-chlorophenyl) Compoundol, 2,2,3,3,3-pentafluoro-1,1-bis (4-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (2-Chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro- 1- (4-chlorophenyl) -1- (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (3-chlorophenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- (3-chlorophenyl) -1- (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (3-Chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (4-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro- 1- (3-chlorophenyl) -1- (4-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (4-chlorophenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (2-chlorophenyl ) Propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro -1- [4- (Trifluoromethyl) phenyl] -1- (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] -1 -(3-Chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (3-chlorophenyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) ) Phenyl] -1- (4-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (4-chlorophenyl) propanol, 2, 2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (4-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2) -Dimethylaminophenyl) -1- (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1- (2-chlorophenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- (4-dimethylaminophenyl) -1- (2-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-dimethylaminophenyl) ) -1- (3-Chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1- (3-chlorophenyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- (4-dimethylaminophenyl) -1- (3-chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-dimethylaminophenyl) -1- (4-Chlorophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1- (4-chlorophenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (4-dimethylaminophenyl) -1- (4-chlorophenyl) propanol, 2,2,3,3 3-Pentafluoro-1- (2-chlorophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (3-nitro) Phenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-Chlorophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (3-nitrophenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- (3-chlorophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1 -(2-Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (4-chlorophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (2-pyridyl) propanol , 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) ) -1- (4-Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3 -Pentafluoro-1- (3-chlorophenyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (4-pyridyl) propanol , 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) ) -1- (3-Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3 -Pentafluoro-1- (2-chlorophenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (3-furyl) propanol ,
2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (3-Frill) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (2-furyl) propanol, 2,2,3,3-3 Pentafluoro-1- (4-chlorophenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (3-thienyl) propanol, 2,2,3,3,3- Pentafluoro-1- (4-chlorophenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-chlorophenyl) -1- (4-biphenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (3-chlorophenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-chlorophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (32-chlorophenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-chlorophenyl) -1- (3-biphenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (4-chlorophenyl) -1- (4-biphenyl) propanol, 4,4,5,5,5-pentafluoro-3- (2-chlorophenyl) -1-phenyl-1-butene-3 -All, 4,4,5,5,5-pen Tafluoro-3- (3-chlorophenyl) -1-phenyl-1-butene-3-ol, 4,4,5,5,5-pentafluoro-3- (4-chlorophenyl) -1-phenyl-1-butene -3-ol, 4,4,5,5,5-pentafluoro-3- (2-chlorophenyl) -1- (2-fluorophenyl) -1-butene-3-ol, 4,4,5,5 , 5-Pentafluoro-3- (2-chlorophenyl) -1- (3-fluorophenyl) -1-butene-3-ol, 4,4,5,5,5-pentafluoro-3- (2-chlorophenyl) ) -1- (4-Fluorophenyl) -1-butene-3-ol, 4,4,5,5,5-pentafluoro-3- (3-chlorophenyl) -1- (2-fluorophenyl) -1 -Butene-3-ol, 4,4,5,5,5-pentafluoro-3- (3-chlorophenyl) -1- (3-fluorophenyl) -1-butene-3-ol, 4,4,5 , 5,5-Pentafluoro-3- (3-chlorophenyl) -1- (4-fluorophenyl) -1-butene-3-ol, 4,4,5,5,5-pentafluoro-3- (4) -Chlorophenyl) -1- (2-fluorophenyl) -1-butene-3-ol, 4,4,5,5,5-pentafluoro-3- (4-chlorophenyl) -1- (3-fluorophenyl) -1-Butene-3-ol, 4,4,5,5,5-pentafluoro-3- (4-chlorophenyl) -1- (4-fluorophenyl) -1-butene-3-ol, 4,4 , 5,5,5-pentafluoro-2,2-dimethyl-3- (2-chlorophenyl) -3-pentanol, 4,4,5,5-pentafluoro-2,2-dimethyl-3-3 Examples thereof include (3-chlorophenyl) -3-butanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (4-chlorophenyl) -3-butanol and the like.
本発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及び/又はR2がブロモフェニル基である化合物としては、具体的には例えば、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(2−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(3−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(4−ブロモフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(4−ピリジル)プロパノール、
2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ブロモフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ブロモフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(32−ブロモフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ブロモフェニル)−1−(4−ビフェニル)プロパノール、4,4,5,5,5−ペンタフルオロ−3−(2−ブロモフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ブロモフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ブロモフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ブロモフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ブロモフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ブロモフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ブロモフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ブロモフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ブロモフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ブロモフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ブロモフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ブロモフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(2−ブロモフェニル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(3−ブロモフェニル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(4−ブロモフェニル)−3−ペンタノール等が挙げられる。
Specific examples of the pentafluoroethyl group-containing alcohols represented by the general formula (2) produced in the production of the present invention and in which R 1 and / or R 2 are bromophenyl groups include 2,2. , 3,3,3-Pentafluoro-1- (2-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (2-bromophenyl) propanol, 2,2,3,3 3-Pentafluoro-1- (2-bromophenyl) -1- (3-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-bromophenyl) -1- (4) -Bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (3-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-) Bromophenyl) -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (4-bromophenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (2-bromophenyl) -1- (2-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (2-bromo) Phenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-bromophenyl) -1- (2-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1 -(2-Bromophenyl) -1- (3-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (3-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-bromophenyl) -1- (3-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-) Bromophenyl) -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (4-bromophenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (4-bromophenyl) -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) ) Phenyl] -1- (2-Bromophenyl) ) Propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (2-bromophenyl) propanol, 2,2,3,3,3-penta Fluoro-1- [4- (trifluoromethyl) phenyl] -1- (2-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (3-Bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (3-bromophenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (3-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2 -(Trifluoromethyl) phenyl] -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (4-) Bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (4-bromophenyl) propanol, 2,2,3,3,3 -Pentafluoro-1- (2-dimethylaminophenyl) -1- (2-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1-( 2-Bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (2-bromophenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (2-dimethylaminophenyl) -1- (3-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1- (3) -Bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (3-bromophenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (2-dimethylaminophenyl) -1- (4-bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1- (4-) Bromophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (4-bromophenyl) propanol, 2,2,3,3 3-Pentafluoro-1- (2-bromophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-bromophenyl) -1- (3) -Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-bromophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro -1- (3-Bromophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (3-nitrophenyl) Propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- ( 4-Bromophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-bromophenyl) -1- (3-nitrophenyl) propanol, 2, 2,3,3,3-pentafluoro-1- (4-bromophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-bromophenyl) ) -1- (2-Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-bromophenyl) -1- (3-pyridyl) propanol, 2,2,3,3 3-Pentafluoro-1- (2-bromophenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (2-) Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-Bromophenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-bromophenyl) -1- (2-pyridyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- (4-bromophenyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-bromophenyl)- 1- (4-pyridyl) propanol,
2,2,3,3,3-pentafluoro-1- (2-bromophenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-bromo) Phenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (2-furyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- (3-bromophenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-bromophenyl) -1- (2) -Frill) propanol, 2,2,3,3,3-pentafluoro-1- (4-bromophenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro-1 -(2-Bromophenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-bromophenyl) -1- (3-thienyl) propanol, 2, 2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-bromophenyl) -1- (2-thienyl) propanol, 2,2,3,3,3 -Pentafluoro-1- (4-bromophenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-bromophenyl) -1- (2-biphenyl) ) Propanol, 2,2,3,3,3-pentafluoro-1- (2-bromophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- ( 2-Bromophenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-bromophenyl) -1- (2-biphenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (3-bromophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (32-bromophenyl) -1 -(4-Biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-bromophenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (4-bromophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro -1- (4-Bromophenyl) -1- (4-biphenyl) propanol, 4,4,5,5,5-pentafluoro-3- (2-bromophenyl) -1-phenyl-1-butene-3 -Ol, 4,4,5,5,5-pentafluoro-3- (3-bromophenyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro- 3- (4-Bromophenyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (2-bromophenyl) -1- (2-fluorophenyl) ) -1-Buten-3-ol, 4,4,5,5,5-pentafluoro-3- (2-bromophenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4 , 4,5,5,5-pentafluoro-3- (2-bromophenyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro -3- (3-Bromophenyl) -1- (2-Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-bromophenyl) -1 -(3-Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-bromophenyl) -1- (4-fluorophenyl) -1-butene -3-ol, 4,4,5,5,5-pentafluoro-3- (4-bromophenyl) -1- (2-fluorophenyl) -1-butene-3-ol, 4,4,5,5 5,5-Pentafluoro-3- (4-bromophenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4) -Bromophenyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (2-bromophenyl)- 3-Pentanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (3-bromophenyl) -3-pentanol, 4,4,5,5,5-pentafluoro Examples thereof include −2,2-dimethyl-3- (4-bromophenyl) -3-pentanol and the like.
本発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及び/又はR2が(トリフルオロメチル)フェニル基である化合物としては、具体的には例えば、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−[2−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−[3−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−[4−(トリフルオロメチル)フェニル]プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル])−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル])−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル])−1−(3−チエニル)プロパノール、
2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル])−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル])−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル])−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル])−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル])−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル])−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル])−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル])−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル])−1−(4−ビフェニル)プロパノール、4,4,5,5,5−ペンタフルオロ−3−[2−(トリフルオロメチル)フェニル]−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[3−(トリフルオロメチル)フェニル]−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[4−(トリフルオロメチル)フェニル]−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[2−(トリフルオロメチル)フェニル]−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[2−(トリフルオロメチル)フェニル]−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[2−(トリフルオロメチル)フェニル]−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[3−(トリフルオロメチル)フェニル]−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[3−(トリフルオロメチル)フェニル]−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[3−(トリフルオロメチル)フェニル]−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[4−(トリフルオロメチル)フェニル]−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[4−(トリフルオロメチル)フェニル]−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−[4−(トリフルオロメチル)フェニル]−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3,3−ジメチル−3−[2−(トリフルオロメチル)フェニル]−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−[3−(トリフルオロメチル)フェニル]−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−[4−(トリフルオロメチル)フェニル]−3−ペンタノール等が挙げられる。
Specific examples of the pentafluoroethyl group-containing alcohol represented by the general formula (2) produced in the production of the present invention, wherein R 1 and / or R 2 is a (trifluoromethyl) phenyl group, include, for example. , 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl ) Phenyl] propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1,1-bis [2- (Trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- [3- (trifluoromethyl) phenyl] Propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- [4- (trifluoromethyl) phenyl] propanol, 2,2,3,3 3-Pentafluoro-1,1-bis [3- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- [4- (Trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1,1-bis [4- (trifluoromethyl) phenyl] propanol, 2,2,3,3 3-Pentafluoro-1- (2-dimethylaminophenyl) -1- [2- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) ) -1- [2- (Trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- [2- (trifluoromethyl) phenyl ] Propanol, 2,2,3,3,3-pentafluoro-1- (2-dimethylaminophenyl) -1- [3- (trifluoromethyl) phenyl] propanol, 2,2,3,3-3 Pentafluoro-1- (3-dimethylaminophenyl) -1- [3- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl)- 1- [3- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (2-dimethylaminofe) Nyl) -1- [4- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1- [4- (trifluoromethyl) Phenyl] propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- [4- (trifluoromethyl) phenyl] propanol, 2,2,3,3,3 -Pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) Phenyl] -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (4-nitrophenyl) propanol, 2 , 2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (Trifluoromethyl) phenyl] -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1-( 4-Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (2-nitrophenyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoro) Methyl) phenyl] -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (Trifluoromethyl) phenyl] -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl]) -1-( 2-Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (3-pyridyl) propanol, 2,2,3,3,3 -Phenyl Luolo-1- [3- (trifluoromethyl) phenyl] -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl]- 1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (3-pyridyl) propanol, 2,2,3 3,3-Pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoro) Methyl) phenyl] -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (3-furyl) propanol, 2 , 2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl]) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (Trifluoromethyl) phenyl] -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (2) -Frill) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (3-furyl) propanol, 2,2,3,3-3 Pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (2-thienyl) propanol, 2,2,3 , 3,3-Pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] Fluoromethyl) phenyl] -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl]) -1- (3-thienyl) propanol ,
2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl]) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1 -[2- (Trifluoromethyl) phenyl]) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl]) -1 -(4-Biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl]) -1- (2-biphenyl) propanol, 2,2,3 3,3-Pentafluoro-1- [3- (trifluoromethyl) phenyl]) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (tri) Fluoromethyl) phenyl]) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl]) -1- (2-biphenyl) Propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl]) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro -1- [4- (Trifluoromethyl) phenyl]) -1- (4-biphenyl) propanol, 4,4,5,5,5-pentafluoro-3- [2- (trifluoromethyl) phenyl]- 1-Phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- [3- (trifluoromethyl) phenyl] -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- [4- (trifluoromethyl) phenyl] -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro -3- [2- (Trifluoromethyl) phenyl] -1- (2-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- [2-( Trifluoromethyl) phenyl] -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- [2- (trifluoromethyl) phenyl]- 1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- [3- (trifluoromethyl) phenyl] -1- (2-fluorophenyl) ) -1-Buten-3-ol, 4,4,5,5,5-pentafluoro-3- [3-( Trifluoromethyl) phenyl] -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- [3- (trifluoromethyl) phenyl]- 1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- [4- (trifluoromethyl) phenyl] -1- (2-fluorophenyl) ) -1-Buten-3-ol, 4,4,5,5,5-pentafluoro-3- [4- (trifluoromethyl) phenyl] -1- (3-fluorophenyl) -1-buten-3 -Ol, 4,4,5,5,5-pentafluoro-3- [4- (trifluoromethyl) phenyl] -1- (4-fluorophenyl) -1-buten-3-ol, 4,4 5,5,5-Pentafluoro-3,3-dimethyl-3- [2- (trifluoromethyl) phenyl] -3-pentanol, 4,4,5,5,5-pentafluoro-2,2- Dimethyl-3- [3- (trifluoromethyl) phenyl] -3-pentanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- [4- (trifluoromethyl) phenyl ] -3-Pentanol and the like.
本発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及び/又はR2がニトロフェニル基である化合物としては、具体的には例えば、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(2−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(3−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(4−ニトロフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(3−ピリジル)プロパノール、
2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ニトロフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ニトロフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(32−ニトロフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−(4−ビフェニル)プロパノール、4,4,5,5,5−ペンタフルオロ−3−(2−ニトロフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ニトロフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ニトロフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ニトロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ニトロフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ニトロフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ニトロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ニトロフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ニトロフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ニトロフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ニトロフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ニトロフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(2−ニトロフェニル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(3−ニトロフェニル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(4−ニトロフェニル)−3−ペンタノール等が挙げられる。
Specific examples of the pentafluoroethyl group-containing alcohol represented by the general formula (2) produced in the production of the present invention, wherein R 1 and / or R 2 is a nitrophenyl group, include 2, 2 , 3,3,3-Pentafluoro-1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (2-nitrophenyl) propanol, 2,2,3,3 3-Pentafluoro-1- (2-nitrophenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-nitrophenyl) -1- (4) -Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-) Nitrophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (4-nitrophenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (2-nitrophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1- (2-nitro) Phenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1 -(2-Nitrophenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-) Nitrophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1- (4-nitrophenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (4-nitrophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) ) Phenyl] -1- (2-nitrophenyl) ) Propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (2-nitrophenyl) propanol, 2,2,3,3,3-penta Fluoro-1- [4- (trifluoromethyl) phenyl] -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (3-Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (3-nitrophenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [2 -(Trifluoromethyl) phenyl] -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (4-) Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (4-nitrophenyl) propanol, 2,2,3,3,3 -Pentafluoro-1- (2-dimethylaminophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1-( 2-Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (2-dimethylaminophenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1- (3) -Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (3-nitrophenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (2-dimethylaminophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1- (4-) Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3 3-Pentafluoro-1- (2-nitrophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-nitrophenyl) -1- (3) -Nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-nitrophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro -1- (3-nitrophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1- (3-nitrophenyl) Propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- ( 4-Nitrophenyl) -1- (2-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1- (3-nitrophenyl) propanol, 2, 2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1- (4-nitrophenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-nitrophenyl) ) -1- (2-Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-nitrophenyl) -1- (3-pyridyl) propanol, 2,2,3,3 3-Pentafluoro-1- (2-nitrophenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1- (2-) Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-Nitrophenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1- (2-pyridyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- (4-nitrophenyl) -1- (3-pyridyl) propanol,
2,2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-nitro) Phenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-nitrophenyl) -1- (3-furyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- (3-nitrophenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1- (3) -Frill) propanol, 2,2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1 -(4-Nitrophenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-nitrophenyl) -1- (2-thienyl) propanol, 2, 2,3,3,3-pentafluoro-1- (2-nitrophenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1- (3-thienyl) propanol, 2,2,3,3,3 -Pentafluoro-1- (4-nitrophenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1- (3-thienyl) ) Propanol, 2,2,3,3,3-pentafluoro-1- (2-nitrophenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- ( 2-Nitrophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-nitrophenyl) -1- (4-biphenyl) propanol, 2,2 3,3,3-Pentafluoro-1- (3-nitrophenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-nitrophenyl) -1 -(3-Biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (32-nitrophenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (4-nitrophenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro- 1- (4-nitrophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1- (4-biphenyl) propanol, 4 , 4,5,5,5-pentafluoro-3- (2-nitrophenyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3) -Nitrophenyl) -1-Phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-nitrophenyl) -1-phenyl-1-buten-3-ol , 4,4,5,5,5-pentafluoro-3- (2-nitrophenyl) -1- (2-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5- Pentafluoro-3- (2-nitrophenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (2-nitrophenyl) -1- (4-Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-nitrophenyl) -1- (2-fluorophenyl) -1 − Buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-nitrophenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4 5,5,5-Pentafluoro-3- (3-nitrophenyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3-3 (4-Nitrophenyl) -1- (2-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-nitrophenyl) -1- (3) −Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-nitrophenyl) -1- (4-fluorophenyl) -1-butene-3-3 All, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (2-nitrophenyl) -3-pentanol, 4,4,5,5,5-pentafluoro-2, 2-Dimethyl-3- (3-nitrophenyl) -3-pentanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (4-nitrophenyl) -3-pentanol And so on.
本発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及び/又はR2がピリジル基である化合物としては、具体的には例えば、2,2,3,3,3−ペンタフルオロ−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ピリジル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ピリジル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ピリジル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ピリジル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ピリジル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ピリジル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ピリジル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ピリジル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ピリジル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ピリジル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ピリジル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ピリジル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ピリジル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ピリジル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ピリジル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ピリジル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ピリジル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ピリジル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ピリジル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ピリジル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ピリジル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ピリジル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ピリジル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ピリジル)−1−(4−ビフェニル)プロパノール、4,4,5,5,5−ペンタフルオロ−3−(2−ピリジル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ピリジル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ピリジル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ピリジル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ピリジル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ピリジル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ピリジル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ピリジル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ピリジル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ピリジル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ピリジル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ピリジル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(2−ピリジル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(3−ピリジル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(4−ピリジル)−3−ペンタノール等が挙げられる。 Pentafluoroethyl group-containing alcohol in represented by the general formula (2) produced in the production of the present invention, as the compound R 1 and / or R 2 is a pyridyl group, specifically, for example, 2,2, 3,3,3-Pentafluoro-1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-pyridyl) propanol, 2,2,3,3-3 Pentafluoro-1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro- 1- (2-pyridyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-pyridyl) -1- (4-pyridyl) propanol, 2,2 , 3,3,3-Pentafluoro-1,1-bis (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-pyridyl) -1- (4-pyridyl) Compoundol, 2,2,3,3,3-pentafluoro-1,1-bis (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-pyridyl) -1- (2-Frill) propanol, 2,2,3,3,3-pentafluoro-1- (2-pyridyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro- 1- (3-pyridyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-pyridyl) -1- (3-furyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- (4-pyridyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-pyridyl) -1- (3-Frill) propanol, 2,2,3,3,3-pentafluoro-1- (2-pyridyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro- 1- (2-pyridyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-pyridyl) -1- (2-thienyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- (3-pyridyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-pyridyl) -1- (2-Thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-pyridyl) -1- (3-thienyl) propanol, 2,2,3,3,3-penta Fluoro-1- (2-pyridyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-pyridyl) -1- (3-biphenyl) propanol, 2 , 2,3,3,3-pentafluoro-1- (2-pyridyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-pyridyl)- 1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-pyridyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (3-pyridyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-pyridyl) -1- (2-biphenyl) propanol, 2 , 2,3,3,3-pentafluoro-1- (4-pyridyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-pyridyl)- 1- (4-biphenyl) propanol, 4,4,5,5,5-pentafluoro-3- (2-pyridyl) -1-phenyl-1-buten-3-ol, 4,4,5,5 5-Pentafluoro-3- (3-pyridyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-pyridyl) -1-phenyl- 1-Buten-3-ol, 4,4,5,5,5-pentafluoro-3- (2-pyridyl) -1- (2-fluorophenyl) -1-buten-3-ol, 4,4 5,5,5-Pentafluoro-3- (2-pyridyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3-( 2-Pyridyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-pyridyl) -1- (2-fluorophenyl) ) -1-Buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-pyridyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4, 4,5,5,5-pentafluoro-3- (3-pyridyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3 -(4-Pyridyl) -1- (2-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-pyridyl) -1- (3-) Fluorophenyl) -1-butene-3-o Le, 4,4,5,5,5-pentafluoro-3- (4-pyridyl) -1- (4-fluorophenyl) -1-butene-3-ol, 4,4,5,5,5- Pentafluoro-2,2-dimethyl-3- (2-pyridyl) -3-pentanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (3-pyridyl) -3 -Pentanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (4-pyridyl) -3-pentanol and the like can be mentioned.
本発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及び/又はR2がビフェニル基である化合物としては、具体的には例えば、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ビス(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[2−(トリフルオロメチル)フェニル]−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[3−(トリフルオロメチル)フェニル]−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−[4−(トリフルオロメチル)フェニル]−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ジメチルアミノフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ジメチルアミノフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ジメチルアミノフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(2−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(3−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(4−ピリジル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(2−フリル)プロパノール、
2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(2−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(3−フリル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(2−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(3−チエニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(2−ビフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(3−ビフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(32−ビフェニル)−1−(4−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(2−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(3−ビフェニル)プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ビフェニル)−1−(4−ビフェニル)プロパノール、4,4,5,5,5−ペンタフルオロ−3−(2−ビフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ビフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ビフェニル)−1−フェニル−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ビフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ビフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(2−ビフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ビフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ビフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(3−ビフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ビフェニル)−1−(2−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ビフェニル)−1−(3−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−3−(4−ビフェニル)−1−(4−フルオロフェニル)−1−ブテン−3−オール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(2−ビフェニル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(3−ビフェニル)−3−ペンタノール、4,4,5,5,5−ペンタフルオロ−2,2−ジメチル−3−(4−ビフェニル)−3−ペンタノール等が挙げられる。
Specific examples of the pentafluoroethyl group-containing alcohols represented by the general formula (2) produced in the production of the present invention and in which R 1 and / or R 2 are biphenyl groups include, for example, 2,2. 3,3,3-Pentafluoro-1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1,1-bis (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro- 1- (2-biphenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (4-biphenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1,1-bis (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (4-biphenyl) Propanol, 2,2,3,3,3-pentafluoro-1,1-bis (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (2-Biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro- 1- (4-biphenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (3-biphenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- (3-biphenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (3-Biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro- 1- (3-biphenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (4-biphenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3-] (Trifluoromethyl) phenyl] -1- (2-biphenyl) propano , 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro- 1- [2- (trifluoromethyl) phenyl] -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) phenyl] -1- (3-Biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (3-biphenyl) propanol, 2,2,3,3 3-Pentafluoro-1- [2- (trifluoromethyl) phenyl] -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- [3- (trifluoromethyl) Phenyl] -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- [4- (trifluoromethyl) phenyl] -1- (4-biphenyl) propanol, 2,2 , 3,3,3-Pentafluoro-1- (2-dimethylaminophenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) ) -1- (2-Biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (2-biphenyl) propanol, 2,2,3,3 , 3-Pentafluoro-1- (2-dimethylaminophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1- (3-Biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-penta Fluoro-1- (2-dimethylaminophenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-dimethylaminophenyl) -1- (4-biphenyl) ) Propanol, 2,2,3,3,3-pentafluoro-1- (4-dimethylaminophenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-Biphenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (3-biphenyl) propanol, 2,2,3 , 3,3- Pentafluoro-1- (2-biphenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (2-biphenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (4-biphenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (3-Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (4-pyridyl) propanol, 2,2,3,3-3 Pentafluoro-1- (3-biphenyl) -1- (2-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (3-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (2-Pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (3-pyridyl) propanol, 2,2,3,3-3 Pentafluoro-1- (4-biphenyl) -1- (4-pyridyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (2-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (2-frill) propanol,
2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (3-furyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (2-Frill) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (3-furyl) propanol, 2,2,3,3-3 Pentafluoro-1- (2-biphenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (2-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (2-thienyl) propanol, 2,2,3,3,3- Pentafluoro-1- (4-biphenyl) -1- (3-thienyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (2-biphenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (3-biphenyl) -1- (2-biphenyl) propanol, 2,2,3,3-3 Pentafluoro-1- (3-biphenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (32-biphenyl) -1- (4-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (2-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (3-biphenyl) propanol, 2,2,3,3,3-pentafluoro-1- (4-biphenyl) -1- (4-biphenyl) propanol, 4,4,5,5,5- Pentafluoro-3- (2-biphenyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-biphenyl) -1-phenyl-1- Buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-biphenyl) -1-phenyl-1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (2-biphenyl) -1- (2-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro -3- (2-biphenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (2-biphenyl) -1-( 4-Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (3-biphenyl) -1- (2-fluorophenyl) -1-buten-3-3 All, 4,4,5,5,5-pentafluoro-3- (3-biphenyl) -1- (3-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5- Pentafluoro-3- (3-biphenyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-biphenyl) -1 -(2-Fluorophenyl) -1-buten-3-ol, 4,4,5,5,5-pentafluoro-3- (4-biphenyl) -1- (3-fluorophenyl) -1-butene- 3-ol, 4,4,5,5,5-pentafluoro-3- (4-biphenyl) -1- (4-fluorophenyl) -1-buten-3-ol, 4,4,5,5 5-Pentafluoro-2,2-dimethyl-3- (2-biphenyl) -3-pentanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (3-biphenyl) Examples thereof include -3-pentanol, 4,4,5,5,5-pentafluoro-2,2-dimethyl-3- (4-biphenyl) -3-pentanol and the like.
本発明の製造で生成する一般式(2)で表わされるペンタフルオロエチル基含有アルコール類で、R1及びR2が結合して環を形成した化合物としては、具体的には例えば、9−(ペンタフルオロエチル)−9−フルオレノール、9−ヒドロキシ−9−(ペンタフルオロエチル)キサンテン、1−(9−アントラセニル)−2,2,3,3,3−おペンタフルオロ−1−プロパノール等が挙げられる。 Specific examples of the pentafluoroethyl group-containing alcohol represented by the general formula (2) produced in the production of the present invention as a compound in which R 1 and R 2 are bonded to form a ring include 9- ( Pentafluoroethyl) -9-fluorenol, 9-hydroxy-9- (pentafluoroethyl) xanthene, 1- (9-anthrasenyl) -2,2,3,3,3-pentafluoro-1-propanol and the like. Be done.
本発明に適用可能な多価のエーテル類としては、具体的には例えば、1,2−ジメトキシエタン、1,2−ジエトキシエタン、1,2−ジブトキシエタン、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、トリエチレングリコールジメチルエーテル、テトラエチレングリコールジエチルエーテル等が挙げられ、反応に具するカリウムtert−ブトキシドもしくはカリウムヘキサメチルジシラジドに対して、2.0モル倍量以上使用する。また、多価エーテル類を反応溶剤として用いても良い。 Specific examples of the polyvalent ethers applicable to the present invention include 1,2-dimethoxyethane, 1,2-diethoxyethane, 1,2-dibutoxyethane, diethylene glycol dimethyl ether, and diethylene glycol diethyl ether. Examples thereof include triethylene glycol dimethyl ether and tetraethylene glycol diethyl ether, which are used in an amount of 2.0 mol times or more based on potassium tert-butoxide or potassium hexamethyldisilazide used in the reaction. Moreover, you may use polyvalent ethers as a reaction solvent.
本発明に適用可能なカリウムtert−ブトキシドもしくはカリウムヘキサメチルジシラジドの使用量としては、反応に具するカルボニル化合物類に対して、1.0モル倍量〜5.0モル倍量使用する。 The amount of potassium tert-butoxide or potassium hexamethyldisilazide applicable to the present invention is 1.0 to 5.0 times the amount of the carbonyl compounds involved in the reaction.
本発明に適用可能なペンタフルオロエタンの使用量としては、反応に具するカルボニル化合物類に対して、1.0モル倍量以上の使用で可能であるが、トリフルオロメタンは気体で、各種溶剤への溶解度が低いために、通常は大過剰使用し、その供給方法としては、バブリングにより反応系に供給する。過剰に供給したペンタフルオロエタンは回収して、再利用しても良い。 The amount of pentafluoroethane applicable to the present invention can be 1.0 mol times or more the amount of the carbonyl compounds involved in the reaction, but trifluoromethane is a gas and can be used in various solvents. Due to its low solubility, it is usually overused and supplied to the reaction system by bubbling. The excessively supplied pentafluoroethane may be recovered and reused.
本発明に適用可能な溶剤としては、反応に不活性なものであればあらゆるものが適用可能であるが、具体的には例えば、ジエチルエーテル、ジイソプロピルエーテル、メチルtert−ブチルエーテル、テトラヒドロフラン等のエーテル系溶剤、ベンゼン、トルエン、エチルベンゼン、キシレン等の芳香族系溶剤、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、ジメチルスルホキシド等の非プトトン系極性溶剤、前記多価エーテル類等が挙げられ、反応に具するカルボニル化合物類に対して、2.0重量倍量〜100重量倍量使用する。これら溶剤は単独で使用しても良いし、混合して使用しても良い。 As the solvent applicable to the present invention, any solvent as long as it is inert to the reaction can be applied. Specifically, for example, an ether system such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, and tetrahydrofuran can be applied. Examples thereof include solvents, aromatic solvents such as benzene, toluene, ethylbenzene, and xylene, non-ptone-based polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, and dimethylsulfoxide, and the polyvalent ethers. 2.0 to 100 times by weight is used with respect to the carbonyl compounds involved in the reaction. These solvents may be used alone or in combination.
本発明の製造の反応温度及び時間としては、-40〜40℃の温度範囲で1〜24時間である。 The reaction temperature and time for the production of the present invention are 1 to 24 hours in the temperature range of −40 to 40 ° C.
本発明の製造の後処理としては、特に規定はなく周知の方法で実施可能で、例えば、飽和の塩化アンモニウム水溶液を添加、ジクロロメタン、ジエチルエーテル等の溶剤で抽出、抽出液を硫酸ナトリウム上で乾燥、ろ過、濃縮し粗製物を得、さらに、シリカゲルカラムクロマトグラフィー等で精製し、一般式(2)で表わされるペンタフルオロエチル基含有アルコール類を得る。 The post-treatment for the production of the present invention is not particularly specified and can be carried out by a well-known method. For example, a saturated aqueous solution of ammonium chloride is added, extracted with a solvent such as dichloromethane or diethyl ether, and the extract is dried on sodium sulfate. , Filter and concentrate to obtain a crude product, and further purify by silica gel column chromatography or the like to obtain pentafluoroethyl group-containing alcohols represented by the general formula (2).
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。 Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited to these Examples.
分析には下記機器を使用した。
1H−NMR(300MHz)、19F−NMR、13C−NMR:ブルカ−・アバンス製500(BurukerAvance500)及びバリアン製マ−キュリ−300(VarianMercury300)。
マススペクトルは、島津製GCMS−QP5050A(SHIMADZUGCMS−QP5050A)。
融点は、ビュッヒ製メルティング・ポイント・M−565(BUCHIMeltingPointM−565)。
赤外吸収(IR)は、日本分光製FT/IR−4100スペクトルメーター(JASCOFT/IR−4100spectrometer)。
The following equipment was used for the analysis.
1 1 H-NMR (300 MHz), 19 F-NMR, 13 C-NMR: Burker Avance 500 and Varian Mercury 300.
The mass spectrum is Shimadzu GCMS-QP5050A (SHIMADZUGCMS-QP5050A).
The melting point is Buch's Melting Point M-565 (BUCHIMeltingPointM-565).
Infrared absorption (IR) is an FT / IR-4100 spectrum meter (JASCOFT / IR-4100 spectrum meter) manufactured by JASCO Corporation.
実施例1
2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノールの調製
Example 1
Preparation of 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol
撹拌子を備えたシュレンク管に、カリウムtert−ブトキシド(44.9mg、0.40mmol、2.0eq.)、トリエチレングリコールジメチルエーテル(1.0mL)を仕込んだ。そのシュレンク管を液体窒素にて冷却、系内を減圧下にし、ペンタフルオロエタンを充填(過剰量)した後、−40℃まで昇温し微量のトリエチレングリコールジメチルエーテルに溶解した4−メトキシベンズアルデヒド(27.2mg、0.20mmol)を加え、−40℃を維持し6時間反応を行った。 Potassium tert-butoxide (44.9 mg, 0.40 mmol, 2.0 eq.) And triethylene glycol dimethyl ether (1.0 mL) were charged into a Schlenk tube equipped with a stir bar. The Schlenk tube was cooled with liquid nitrogen, the inside of the system was reduced under reduced pressure, pentafluoroethane was filled (excessive amount), and then the temperature was raised to -40 ° C and 4-methoxybenzaldehyde dissolved in a trace amount of triethylene glycol dimethyl ether (4-methoxybenzaldehyde). 27.2 mg (0.20 mmol) was added, and the reaction was carried out at −40 ° C. for 6 hours.
反応終了後、飽和塩化アンモニウム水溶液を添加、分液し有機層を得、さらに水層はジエチルエーテルにより抽出し、有機層を合わせて硫酸ナトリウム上で乾燥、ろ過、濃縮することにより、粗製物を得た(19F−NMRによる粗収率99%以上)。得られた粗製物は、シリカゲルカラムクロマトグラフィーで精製することにより、目的物の2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノールを得た(50.2mg、0.20mmol、収率98%)。 After completion of the reaction, a saturated aqueous solution of ammonium chloride was added and separated to obtain an organic layer, and the aqueous layer was extracted with diethyl ether, and the organic layers were combined and dried, filtered and concentrated on sodium sulfate to obtain a crude product. Obtained ( 19 F-NMR crude yield of 99% or more). The obtained crude product was purified by silica gel column chromatography to obtain the desired product 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol (50). .2 mg, 0.20 mmol, 98% yield).
実施例2
2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノールの調製
実施例1と同じ反応装置を用い、トリエチレングリコールジメチルエーテルに替えて、表1に示したテトラエチレングリコールを用いた以外は、実施例1と同じ反応操作を行った。反応終了後は実施例1と同様の操作で粗製物を得るところまで行い、目的物の2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノールを得た(19F−NMRによる粗収率99%以上)。
Example 2
Preparation of 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol Using the same reactor as in Example 1 and replacing it with triethylene glycol dimethyl ether, it is shown in Table 1. The same reaction operation as in Example 1 was carried out except that tetraethylene glycol was used. After completion of the reaction, the same operation as in Example 1 was carried out until a crude product was obtained to obtain the target product 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol. ( 19 The crude yield by F-NMR is 99% or more).
実施例3
2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノールの調製
実施例1と同じ反応装置を用い、表1に示したペンタフルオロエタンの当量数を変えた以外は、実施例1と同じ反応操作を行った。反応終了後は実施例1と同様の操作で粗製物を得るところまで行い、目的物の2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノールを得た(19F−NMRによる粗収率99%)。
Example 3
Preparation of 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol Using the same reactor as in Example 1, the equivalent number of pentafluoroethane shown in Table 1 was changed. Except for the above, the same reaction operation as in Example 1 was performed. After completion of the reaction, the same operation as in Example 1 was carried out until a crude product was obtained to obtain the target product 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol. ( 19 % crude yield by F-NMR).
実施例4
2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノールの調製
実施例1と同じ反応装置を用い、表1に示した反応温度を変えた以外は、実施例1と同じ反応操作を行った。反応終了後は実施例1と同様の操作で粗製物を得るところまで行い、目的物の2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノールを得た(19F−NMRによる粗収率96%)。
Example 4
Preparation of 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol except that the reaction temperature shown in Table 1 was changed using the same reaction apparatus as in Example 1. The same reaction operation as in Example 1 was performed. After completion of the reaction, the same operation as in Example 1 was carried out until a crude product was obtained to obtain the target product 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol. ( 19 F-NMR crude yield 96%).
実施例5
1)2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノールの調製
実施例1と同じ反応装置を用い、トリエチレングリコールジメチルエーテルに替えて、表1に示したトルエン溶媒を用い、添加剤としてトリエチレングリコールジメチルエーテルを用いた以外は、実施例1と同じ反応操作を行った。反応終了後は実施例1と同様の操作で粗製物を得るところまで行い、目的物の2,2,2−トリフルオロ−1,1−ジフェニルエタノールを得た(19F−NMRによる粗収率88%)。
Example 5
1) Preparation of 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol Using the same reactor as in Example 1 and replacing with triethylene glycol dimethyl ether, Table 1 shows. The same reaction operation as in Example 1 was carried out except that the toluene solvent shown was used and triethylene glycol dimethyl ether was used as an additive. After completion of the reaction, the same operation as in Example 1 was carried out until a crude product was obtained to obtain the target product 2,2,2-trifluoro-1,1-diphenylethanol ( 19 crude yield by F-NMR). 88%).
実施例6
2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノールの調製
実施例1と同じ反応装置を用い、トリエチレングリコールジメチルエーテルに替えて、表1に示したテトラヒドロフラン溶媒を用い、添加剤として1,10−ジアザ−4,7,13,16,24,24−ヘキサオキサビジクロ[8,8,8]ヘキサコン(112.9mg、0.30mmol)を用い、反応温度を-10℃とした以外は、実施例1と同じ反応操作を行った。反応終了後は実施例1と同様の操作で粗体として2,2,2−トリフルオロ−1,1−ジフェニルエタノールを得た(19F−NMRによる粗収率99%以上)。その後、実施例1と同様の操作で粗製物を精製することで目的の2,2,2,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノール(98%)を得た。
Example 6
Preparation of 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol Using the same reactor as in Example 1 and replacing it with triethylene glycol dimethyl ether, it is shown in Table 1. Using a tetrahydrofuran solvent and using 1,10-diaza-4,7,13,16,24,24-hexoxavidiculo [8,8,8] hexacon (112.9 mg, 0.30 mmol) as an additive, The same reaction operation as in Example 1 was carried out except that the reaction temperature was set to −10 ° C. After completion of the reaction, 2,2,2-trifluoro-1,1-diphenylethanol was obtained as a crude product by the same operation as in Example 1 ( 19 F-NMR crude yield of 99% or more). Then, the crude product was purified by the same operation as in Example 1 to obtain the desired 2,2,2,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol (98%). rice field.
実施例7〜17 各種ペンタフルオロエチル基含有アルコール類の調整
実施例1と同じ反応装置を用い、4−メトキシベンズアルデヒドに替えて表2中に示したカルボニル化合物類を用いた以外は実施例1と同じ反応操作を行い、ペンタフルオロエチル基含有アルコール類を得た。結果を表2中に示した。
Examples 7 to 17 Preparation of various pentafluoroethyl group-containing alcohols Same as Example 1 except that the carbonyl compounds shown in Table 2 were used instead of 4-methoxybenzaldehyde using the same reaction apparatus as in Example 1. The same reaction operation was carried out to obtain pentafluoroethyl group-containing alcohols. The results are shown in Table 2.
実施例18 2,2,2,3,3−ペンタフルオロ−1,1−ジフェニルエタノールの調整
撹拌子を備えたシュレンク管に、カリウムtert−ブトキシド(89.8mg、0.40mmol、2.0eq.)、トリエチレングリコールジメチルエーテル(0.5mL)を仕込んだ。そのシュレンク管を液体窒素にて冷却、系内を減圧下にし、ペンタフルオロエタンを充填(過剰量)した後、室温まで昇温し微量のトリエチレングリコールジメチルエーテルに溶解したベンゾフェノン(36.4mg、0.20mmol)を加え、室温を維持し7時間反応を行った。
Example 18 Preparation of 2,2,2,3,3-pentafluoro-1,1-diphenylethanol Potassium tert-butoxide (89.8 mg, 0.40 mmol, 2.0 eq. ), Triethylene glycol dimethyl ether (0.5 mL) was charged. The Schlenk tube was cooled with liquid nitrogen, the inside of the system was depressurized, pentafluoroethane was filled (excessive amount), and then the temperature was raised to room temperature and benzophenone (36.4 mg, 0) dissolved in a trace amount of triethylene glycol dimethyl ether. .20 mmol) was added, and the reaction was carried out for 7 hours at room temperature.
反応終了後、飽和塩化アンモニウム水溶液を添加、分液し有機層を得、さらに水層はジエチルエーテルにより抽出し、有機層を合わせて硫酸ナトリウム上で乾燥、ろ過、濃縮することにより、粗製物を得た(19F−NMRによる粗収率80%)。得られた粗製物は、シリカゲルカラムクロマトグラフィーで精製することにより、目的物の2,2,2,3,3−ペンタフルオロ−1,1,−ジフェニルエタノールを得た(46.6mg、0.15mmol、収率77%)。 After completion of the reaction, a saturated aqueous solution of ammonium chloride was added and separated to obtain an organic layer, and the aqueous layer was extracted with diethyl ether, and the organic layers were combined and dried, filtered and concentrated on sodium sulfate to obtain a crude product. Obtained ( 19 crude yield by F-NMR 80%). The obtained crude product was purified by silica gel column chromatography to obtain the desired product 2,2,2,3,3-pentafluoro-1,1, -diphenylethanol (46.6 mg, 0. 15 mmol, yield 77%).
実施例19
2,2,2,3,3−ペンタフルオロ−1,1−ジフェニルエタノールの調整
実施例18と同じ反応装置を用い、表3に示したペンタフルオロエタンの当量、tert−ブトキシカリウムの当量を変えた以外は、実施例18と同じ反応操作を行った。反応終了後は実施例18と同様の操作で粗製物を得た(19F−NMRによる粗収率69%)。その後、粗製物を実勢例18と同様に精製し目的物の2,2,2,3,3−ペンタフルオロ−1,1,−ジフェニルエタノールを得た(39.3mg,0.13mmol,収率65%)。
Example 19
Preparation of 2,2,2,3,3-pentafluoro-1,1-diphenylethanol Using the same reactor as in Example 18, the equivalent of pentafluoroethane and the equivalent of tert-butoxypotassium shown in Table 3 were changed. Except for the above, the same reaction operation as in Example 18 was carried out. After completion of the reaction, a crude product was obtained by the same operation as in Example 18 ( 19 F-NMR crude yield 69%). Then, the crude product was purified in the same manner as in Example 18 to obtain the target product 2,2,2,3,3-pentafluoro-1,1, -diphenylethanol (39.3 mg, 0.13 mmol, yield). 65%).
実施例20
2,2,2,3,3−ペンタフルオロ−1,1−ジフェニルエタノールの調整
実施例18と同じ反応装置を用い、溶媒をトリエチレングリコールに替えて表3に示したテトラエチレングリコールとし、ペンタフルオロエタンの当量、tert−ブトキシカリウムの当量を変えた以外は、実施例18と同じ反応操作を行った。反応終了後は実施例18と同様の操作で粗製物を得た(19F−NMRによる粗収率68%)。
Example 20
Preparation of 2,2,2,3,3-pentafluoro-1,1-diphenylethanol Using the same reactor as in Example 18, the solvent was changed to triethylene glycol to tetraethylene glycol shown in Table 3, and penta. The same reaction procedure as in Example 18 was carried out except that the equivalent of fluoroethane and the equivalent of tert-butoxypotassium were changed. After completion of the reaction, a crude product was obtained by the same operation as in Example 18 ( 19 F-NMR crude yield 68%).
実施例21
2,2,2,3,3−ペンタフルオロ−1,1−ジフェニルエタノールの調整
実施例18と同じ反応装置を用い、溶媒をトリエチレングリコールに替えて表3に示したN,N−ジメチルホルムアミドとし、ペンタフルオロエタンの当量、tert−ブトキシカリウムの当量を変えた以外は、実施例18と同じ反応操作を行った。反応終了後は実施例18と同様の操作で粗製物を得た(19F−NMRによる粗収率9%)。
Example 21
Preparation of 2,2,2,3,3-pentafluoro-1,1-diphenylethanol Using the same reactor as in Example 18, the solvent was changed to triethylene glycol, and the N, N-dimethylformamide shown in Table 3 was used. The same reaction operation as in Example 18 was carried out except that the equivalent of pentafluoroethane and the equivalent of tert-butoxypotassium were changed. After completion of the reaction, a crude product was obtained by the same operation as in Example 18 ( 19 F-NMR crude yield 9%).
実施例22〜28
各種ペンタフルオロエチル基含有アルコール類の調整
実施例18と同じ反応装置を用い、ベンゾフェノンに替えて表4中に示したカルボニル化合物類を用いた以外は実施例19と同じ反応操作を行い、ペンタフルオロエチル基含有アルコール類を得た。結果を表4中に示した。
Examples 22-28
Preparation of various pentafluoroethyl group-containing alcohols Using the same reaction apparatus as in Example 18, the same reaction operation as in Example 19 was carried out except that the carbonyl compounds shown in Table 4 were used instead of benzophenone, and pentafluoro was performed. Ethyl group-containing alcohols were obtained. The results are shown in Table 4.
実施例29
3,3,4,4,4−ペンタフルオロ−2−(4−メトキシフェニル)−2−ブタノール
撹拌子を備えたシュレンク管に、カリウムtert−ブトキシド(73.3mg、0.60mmol、3.0eq.)、テトラエチレングリコールジメチルエーテル(2.0mL)を仕込んだ。そのシュレンク管を液体窒素にて冷却、系内を減圧下にし、ペンタフルオロエタンを充填(過剰量)した後、室温まで昇温し微量のテトラエチレングリコールジメチルエーテルに溶解した4−メトキシアセトフェノン(30.0mg、0.20mmol)を加え、室温を維持し12時間反応を行った。
Example 29
3,3,4,5,4-Pentafluoro-2- (4-methoxyphenyl) -2-butanol In a Schlenk tube equipped with a stir bar, potassium tert-butoxide (73.3 mg, 0.60 mmol, 3.0 eq) ), Tetraethylene glycol dimethyl ether (2.0 mL) was charged. The Schlenk tube was cooled with liquid nitrogen, the inside of the system was reduced under reduced pressure, pentafluoroethane was filled (excessive amount), and then the temperature was raised to room temperature and 4-methoxyacetophenone dissolved in a trace amount of tetraethylene glycol dimethyl ether (30. (0 mg, 0.20 mmol) was added, and the reaction was carried out for 12 hours while maintaining room temperature.
反応終了後、飽和塩化アンモニウム水溶液を添加、分液し有機層を得、さらに水層はジエチルエーテルにより抽出し、有機層を合わせて硫酸ナトリウム上で乾燥、ろ過、濃縮することにより、粗製物を得た(19F−NMRによる粗収率86%)。得られた粗製物は、シリカゲルカラムクロマトグラフィーで精製することにより、目的物の3,3,4,4,4−ペンタフルオロ−2−(4−メトキシフェニル)−2−ブタノールを得た(43.2mg、0.16mmol、収率80%)。 After completion of the reaction, a saturated aqueous solution of ammonium chloride was added and separated to obtain an organic layer, and the aqueous layer was extracted with diethyl ether, and the organic layers were combined and dried, filtered and concentrated on sodium sulfate to obtain a crude product. Obtained ( 19 F-NMR crude yield 86%). The obtained crude product was purified by silica gel column chromatography to obtain the desired product 3,3,4,5,4-pentafluoro-2- (4-methoxyphenyl) -2-butanol (43). .2 mg, 0.16 mmol, yield 80%).
実施例30
3,3,4,4,4−ペンタフルオロ−2−フェニル−2−ブタノール
実施例29と同じ反応装置を用い、反応温度を−10℃に変えた以外は、実施例29と同じ反応操作を行った。反応終了後は実施例29と同様の操作で粗製物を得た(19F−NMRによる粗収率91%)。
Example 30
3,3,4,5,4-Pentafluoro-2-phenyl-2-butanol The same reaction operation as in Example 29 was carried out except that the reaction temperature was changed to −10 ° C. using the same reaction apparatus as in Example 29. went. After completion of the reaction, a crude product was obtained by the same operation as in Example 29 ( 19 F-NMR crude yield 91%).
実施例31
3,3,4,4,4−ペンタフルオロ−2−フェニル−2−ブタノール
実施例29と同じ反応装置を用い、溶媒をテトラエチレングリコールジメチルエーテルに替えて、トリエチレングリコールジメチルエーテル、反応温度を−10℃に変えた以外は、実施例29と同じ反応操作を行った。反応終了後は実施例29と同様の操作で粗製物を得た(19F−NMRによる粗収率81%)。
Example 31
3,3,4,5,4-Pentafluoro-2-phenyl-2-butanol Using the same reaction apparatus as in Example 29, the solvent was changed to tetraethylene glycol dimethyl ether, triethylene glycol dimethyl ether was used, and the reaction temperature was -10. The same reaction operation as in Example 29 was carried out except that the temperature was changed to ° C. After completion of the reaction, a crude product was obtained by the same operation as in Example 29 ( 19 F-NMR crude yield 81%).
実施例32〜37
各種ペンタフルオロエチル基含有アルコール類の調整
実施例29と同じ反応装置を用い、4−メトキシアセトフェノンに替えて表5中に示したカルボニル化合物類を用いた以外は実施例29と同じ反応操作を行い、ペンタフルオロエチル基含有アルコール類を得た。結果を表5中に示した。
Examples 32 to 37
Preparation of various pentafluoroethyl group-containing alcohols Using the same reaction apparatus as in Example 29, the same reaction operation as in Example 29 was carried out except that the carbonyl compounds shown in Table 5 were used instead of 4-methoxyacetophenone. , Pentafluoroethyl group-containing alcohols were obtained. The results are shown in Table 5.
実施例38
(E)−4,4,5,5,5−ペンタフルオロ−1,3−ジフェニル−1−ペンテン−3−オールの調整
撹拌子を備えたシュレンク管に、カリウムヘキサメチルジシラジド(159.6mg、0.80mmol、4.0eq.)、トリエチレングリコールジメチルエーテル(0.5mL)を仕込んだ。そのシュレンク管を液体窒素にて冷却、系内を減圧下にし、ペンタフルオロエタンを充填(過剰量)した後、−40℃まで昇温し微量のトリエチレングリコールジメチルエーテルに溶解したカルコン(41.7mg、0.20mmol)を加え、−40℃を維持し12時間反応を行った。
Example 38
(E) Adjustment of -4,4,5,5,5-pentafluoro-1,3-diphenyl-1-pentene-3-ol In a Schlenk tube equipped with a stirrer, potassium hexmethyldisilazide (159. 6 mg, 0.80 mmol, 4.0 eq.) And triethylene glycol dimethyl ether (0.5 mL) were charged. The Schlenk tube was cooled with liquid nitrogen, the inside of the system was reduced under reduced pressure, pentafluoroethane was filled (excessive amount), and then the temperature was raised to -40 ° C and chalcone dissolved in a trace amount of triethylene glycol dimethyl ether (41.7 mg). , 0.20 mmol) was added, and the reaction was carried out at −40 ° C. for 12 hours.
反応終了後、飽和塩化アンモニウム水溶液を添加、分液し有機層を得、さらに水層はジエチルエーテルにより抽出し、有機層を合わせて硫酸ナトリウム上で乾燥、ろ過、濃縮することにより、粗製物を得た(19F−NMRによる粗収率89%)。得られた粗製物は、シリカゲルカラムクロマトグラフィーで精製することにより、目的物の(E)−4,4,5,5,5−ペンタフルオロ−1,3−ジフェニル−1−ペンテン−3−オールを得た(54.5mg、0.17mmol、収率83%)。 After completion of the reaction, a saturated aqueous solution of ammonium chloride was added and separated to obtain an organic layer, and the aqueous layer was extracted with diethyl ether, and the organic layers were combined and dried, filtered and concentrated on sodium sulfate to obtain a crude product. Obtained ( 19 % crude yield by F-NMR). The obtained crude product was purified by silica gel column chromatography to obtain the desired product (E) -4,4,5,5,5-pentafluoro-1,3-diphenyl-1-pentene-3-ol. Was obtained (54.5 mg, 0.17 mmol, yield 83%).
実施例39
(E)−4,4,5,5,5−ペンタフルオロ−1,3−ジフェニル−1−ペンテン−3−オールの調整
実施例38と同じ反応装置を用い、表6に示したカリウムヘキサメチルジシラジドの当量を変えた以外は、実施例38と同じ反応操作を行った。反応終了後は実施例38と同様の操作で粗製物を得た(19F−NMRによる粗収率85%)。
Example 39
(E) Preparation of -4,4,5,5,5-pentafluoro-1,3-diphenyl-1-pentene-3-ol Using the same reaction apparatus as in Example 38, potassium hexmethyl shown in Table 6 The same reaction operation as in Example 38 was carried out except that the equivalent amount of disilazide was changed. After completion of the reaction, a crude product was obtained by the same operation as in Example 38 (crude yield 85% by 19 F-NMR).
実施例40
(E)−4,4,5,5,5−ペンタフルオロ−1,3−ジフェニル−1−ペンテン−3−オールの調整
実施例38と同じ反応装置を用い、表6に示したカリウムヘキサメチルジシラジドの当量、ペンタフルオロエタンの当量を変えた以外は、実施例38と同じ反応操作を行った。反応終了後は実施例38と同様の操作で粗製物を得た(19F−NMRによる粗収率77%)。
Example 40
(E) Preparation of -4,4,5,5,5-pentafluoro-1,3-diphenyl-1-pentene-3-ol Using the same reaction apparatus as in Example 38, potassium hexamethyl shown in Table 6 The same reaction operation as in Example 38 was carried out except that the equivalent of disilazide and the equivalent of pentafluoroethane were changed. After completion of the reaction, a crude product was obtained by the same operation as in Example 38 (crude yield 77% by 19 F-NMR).
実施例41
(E)−4,4,5,5,5−ペンタフルオロ−1,3−ジフェニル−1−ペンテン−3−オールの調整
実施例38と同じ反応装置を用い、溶媒をトリエチレングリコールジメチルエーテルに替えて表6に示したテトラエチレングリコールジメチルエーテルとし、カリウムヘキサメチルジシラジドの当量を変えた以外は、実施例38と同じ反応操作を行った。反応終了後は実施例38と同様の操作で粗製物を得た(19F−NMRによる粗収率84%)。
Example 41
(E) Preparation of -4,4,5,5,5-pentafluoro-1,3-diphenyl-1-pentene-3-ol Using the same reactor as in Example 38, the solvent was changed to triethylene glycol dimethyl ether. The same reaction operation as in Example 38 was carried out except that the tetraethylene glycol dimethyl ether shown in Table 6 was used and the equivalent amount of potassium hexamethyldisilazide was changed. After completion of the reaction, a crude product was obtained by the same operation as in Example 38 (crude yield 84% by 19 F-NMR).
実施例42〜46
各種ペンタフルオロエチル基含有アルコール類の調整
実施例38と同じ反応装置を用い、カルコンに替えて表7中に示したカルボニル化合物類を用いた以外は実施例38と同じ反応操作を行い、ペンタフルオロエチル基含有アルコール類を得た。結果を表7中に示した。
Examples 42-46
Preparation of various pentafluoroethyl group-containing alcohols Using the same reaction apparatus as in Example 38, the same reaction operation as in Example 38 was carried out except that the carbonyl compounds shown in Table 7 were used instead of chalcone, and pentafluoro was performed. Ethyl group-containing alcohols were obtained. The results are shown in Table 7.
2,2,3,3,3−ペンタフルオロ−1−(4−メトキシフェニル)−1−プロパノール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:7.38(d,J=8.3Hz,2H),6.93(d,J=8.7Hz,2H),5.13−5.00(m,1H),3.83(s,3H),2.51(d,J=4.9Hz,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-81.75(s,3F),-122.66(dd,J=274.9,8.0Hz,1F),-129.89(dd,J=274.9,16.4Hz,1F)。
MS(EI,m/z)255[M-H−]。
2,2,3,3,3-pentafluoro-1- (4-methoxyphenyl) -1-propanol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.38 (d, J = 8.3 Hz, 2H), 6.93 (d, J = 8.7 Hz, 2H), 5.13-5.00 (M, 1H), 3.83 (s, 3H), 2.51 (d, J = 4.9Hz, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -81.75 (s, 3F), -122.66 (dd, J = 274.9, 8.0Hz, 1F), -129.89 (dd, dd, J = 274.9, 16.4 Hz, 1F).
MS (EI, m / z) 255 [M-H -].
2)2,2,3,3,3−ペンタフルオロ−1−フェニル−1−プロパノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.49-7.37(m,5H),5.17-5.04(m,1H),2.57(d,J=4.2Hz,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-81.76(s,3F),-122.41(dd,J=275.9,7.4H,1F),-129.90(dd,J=275.7,16.6Hz,1F)
2) 2,2,3,3,3-pentafluoro-1-phenyl-1-propanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.49-7.37 (m, 5H), 5.17-5.04 (m, 1H), 2.57 (d, J = 4.2 Hz) , 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -81.76 (s, 3F), -122.41 (dd, J = 275.9, 7.4H, 1F), -129.90 (dd, dd, J = 275.7, 16.6Hz, 1F)
3)2,2,3,3,3−ペンタフルオロ−1−(4−フルオロフェニル)−1−プロパノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.52-7.38(m,2H),7.17-7.05(m,2H),5.20-5.05(m,1H),2.58(d,J=4.8Hz,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-81.66(s,3F),-111.85--112.10(m,1F),-122.52(dd,J=275.9,7.5Hz,1F),-129.79(dd,J=275.9,16.2Hz,1F)。
MS(EI,m/z)243[M-H−]。
3) 2,2,3,3,3-pentafluoro-1- (4-fluorophenyl) -1-propanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.52-7.38 (m, 2H), 7.17-7.05 (m, 2H), 5.20-5.05 (m, 1H) ), 2.58 (d, J = 4.8 Hz, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -81.66 (s, 3F), -111.85--112.10 (m, 1F), -122.52 (dd, J = 275.9) , 7.5Hz, 1F), -129.79 (dd, J = 275.9, 16.2Hz, 1F).
MS (EI, m / z) 243 [M-H -].
4)2,2,3,3,3−ペンタフルオロ−1−(4−(トリフルオロメトキシ)フェニル)−1−プロパノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.51(d,J=8.4Hz,2H),7.27(d,J=8.1Hz,2H),5.23-5.08(m,1H),2.64(d,J=4.9Hz,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-58.30(s,3F),-81.58(s,3F),-122.13(dd,J=276.5,7.3Hz,1F),-129.76(dd,J=276.6,16.1Hz,1F)。
MS(EI,m/z)309[M-H−]。
4) 2,2,3,3,3-pentafluoro-1- (4- (trifluoromethoxy) phenyl) -1-propanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.51 (d, J = 8.4 Hz, 2H), 7.27 (d, J = 8.1 Hz, 2H), 5.23-5.08 (M, 1H), 2.64 (d, J = 4.9Hz, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -58.30 (s, 3F), -181.58 (s, 3F), -122.13 (dd, J = 276.5,7.3Hz, 1F), -129.76 (dd, J = 276.6, 16.1Hz, 1F).
MS (EI, m / z) 309 [M-H -].
5)1−([1,1−ビフェニル−4−イル]−2,2,3,3,3−ペンタフルオロ−1−プロパノール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:7.69-7.34(m,9H),5.25-5.11(m,1H),2.57(d,J=4.7Hz,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-81.67(s,3F),-122.08(dd,J=275.6,7.3Hz,1F),-129.87(dd,J=275.8,16.7Hz,1F)。
MS(EI,m/z)301[M-H−]。
5) 1-([1,1-biphenyl-4-yl] -2,2,3,3,3-pentafluoro-1-propanol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.69-7.34 (m, 9H), 5.25-5.11 (m, 1H), 2.57 (d, J = 4.7 Hz) , 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -81.67 (s, 3F), -122.08 (dd, J = 275.6, 7.3Hz, 1F), -129.87 (dd, dd, J = 275.8, 16.7 Hz, 1F).
MS (EI, m / z) 301 [M-H -].
6)2,2,3,3,3−ペンタフルオロ−1−(p−トルイル)−1−プロパノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ;7.34(d,J=7.8Hz,2H),7.22(d,J=7.8Hz,2H),5.16-5.00(m,1H),2.50(d,J=4.6Hz,1H),2.38(s,3H)。
19F−NMR(282MHz,Chloroform−d)δ:-81.75(s,3F),-122.44(dd,J=275.4,7.5Hz,1F),-129.91(dd,J=275.3,16.7Hz,1F)。
MS(EI,m/z)239[M-H−]。
6) 2,2,3,3,3-pentafluoro-1- (p-toluyl) -1-propanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ; 7.34 (d, J = 7.8 Hz, 2H), 7.22 (d, J = 7.8 Hz, 2H), 5.16-5.00 (M, 1H), 2.50 (d, J = 4.6Hz, 1H), 2.38 (s, 3H).
19 F-NMR (282MHz, Chloroform-d) δ: -81.75 (s, 3F), -122.44 (dd, J = 275.4,7.5Hz, 1F), -129.91 (dd, J = 275.3, 16.7 Hz, 1F).
MS (EI, m / z) 239 [M-H -].
7)1−(4−ブロモフェニル)−2,2,3,3,3−ペンタフルオロ−1−プロパノール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:7.56(d,J=8.5Hz,2H),7.34(d,J=8.1Hz,2H),5.17-5.03(m,1H),2.51(d,J=5.0Hz,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-81.58(s,3F),-122.06(dd,J=276.1,7.3Hz,1F),-129.71(dd,J=276.3,16.3Hz,1F)。
MS(EI,m/z)303[M-H−]。
7) 1- (4-Bromophenyl) -2,2,3,3,3-pentafluoro-1-propanol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.56 (d, J = 8.5 Hz, 2H), 7.34 (d, J = 8.1 Hz, 2H), 5.17-5.03 (M, 1H), 2.51 (d, J = 5.0Hz, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -81.58 (s, 3F), -122.06 (dd, J = 276.1,7.3Hz, 1F), -129.71 (dd, dd, J = 276.3, 16.3 Hz, 1F).
MS (EI, m / z) 303 [M-H -].
8)1−(4−クロロフェニル)−2,2,3,3,3−ペンタフルオロ−1−プロパノール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:7.48-7.33(m,4H),5.20-5.04(m,1H),2.57(d,J=5.0Hz,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-81.59(s,3F),-122.22(dd,J=276.4,7.4Hz,1F),-129.64(dd,J=276.3,16.0Hz,1F)。
MS(EI,m/z)259[M-H−]。
8) 1- (4-chlorophenyl) -2,2,3,3,3-pentafluoro-1-propanol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.48-7.33 (m, 4H), 5.20-5.04 (m, 1H), 2.57 (d, J = 5.0 Hz) , 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -81.59 (s, 3F), -122.22 (dd, J = 276.4, 7.4Hz, 1F), -129.64 (dd, dd, J = 276.3, 16.0 Hz, 1F).
MS (EI, m / z) 259 [M-H -].
9)2,2,3,3,3−ペンタフルオロ−1−(4−ヨードフェニル)−1−プロパノール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:7.76(d,J=8.4Hz,2H),7.20(d,J=8.1Hz,2H),5.08(dd,J=16.2,7.3Hz,1H),2.61(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-81.62(s,3F),-122.17(dd,J=276.4,7.3H,1F),-129.79(dd,J=276.2,16.2Hz,1F)。
MS(EI,m/z)351[M-H−]。
9) 2,2,3,3,3-pentafluoro-1- (4-iodophenyl) -1-propanol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.76 (d, J = 8.4 Hz, 2H), 7.20 (d, J = 8.1 Hz, 2H), 5.08 (dd, J) = 16.2, 7.3 Hz, 1H), 2.61 (s, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -81.62 (s, 3F), -122.17 (dd, J = 276.4,7.3H, 1F), -129.79 (dd, dd, J = 276.2, 16.2 Hz, 1F).
MS (EI, m / z) 351 [M-H -].
10)1−(3−ブロモフェニル)−2,2,3,3,3−ペンタフルオロ−1−プロパノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.55(s,1H),7.48(d,J=7.9Hz,1H),7.31(d,J=7.7Hz,1H),7.25-7.15(m,1H),5.02(dd,J=16.4,7.0Hz,1H),2.57(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-81.62(s,3F),-121.73(dd,J=276.7,6.9Hz,1F),-129.86(dd,J=276.6,16.5Hz,1F)。
MS(EI,m/z)303[M-H−]。
10) 1- (3-Bromophenyl) -2,2,3,3,3-pentafluoro-1-propanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.55 (s, 1H), 7.48 (d, J = 7.9 Hz, 1H), 7.31 (d, J = 7.7 Hz, 1H) ), 7.25-7.15 (m, 1H), 5.02 (dd, J = 16.4, 7.0 Hz, 1H), 2.57 (s, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -81.62 (s, 3F), -121.73 (dd, J = 276.7, 6.9Hz, 1F), -129.86 (dd, dd, J = 276.6, 16.5 Hz, 1F).
MS (EI, m / z) 303 [M-H -].
11)1−(2−ブロモフェニル)−2,2,3,3,3−ペンタフルオロ−1−プロパノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.67(d,J=7.8Hz,1H),7.60(d,J=8.0Hz,1H),7.40(td,J=7.6,1.3Hz,1H),7.27(td,J=7.7,1.7Hz,1H),5.78(dt,J=18.2,4.9Hz,1H),2.63(d,J=4.8Hz,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-82.37(s,3F),-121.23(dd,J=277.5,4.6Hz,1F),-131.08(dd,J=277.6,18.1Hz,1F)。
MS(EI,m/z)303[M-H−]。
11) 1- (2-Bromophenyl) -2,2,3,3,3-pentafluoro-1-propanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.67 (d, J = 7.8 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 7.40 (td, J) = 7.6, 1.3Hz, 1H), 7.27 (td, J = 7.7, 1.7Hz, 1H), 5.78 (dt, J = 18.2, 4.9Hz, 1H), 2.63 (d, J = 4.8 Hz, 1 H).
19 F-NMR (282MHz, Chloroform-d) δ: -82.37 (s, 3F), -121.23 (dd, J = 277.5, 4.6Hz, 1F), -131.08 (dd, 3F) J = 277.6, 18.1 Hz, 1F).
MS (EI, m / z) 303 [M-H -].
12)2,2,3,3,3−ペンタフルオロ−1−(ナフタレン−2−イル)−1−プロパノール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:8.00-7.82(m,4H),7.62-7.47(m,3H),5.38-5.22(m,1H),2.55(d,J=5.0Hz,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-81.69(s,3F),-122.01(dd,J=275.9,7.4Hz,1F),-129.47(dd,J=275.9,16.7Hz,1F)。
MS(EI,m/z)275[M-H−]。
12) 2,2,3,3,3-pentafluoro-1- (naphthalene-2-yl) -1-propanol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 8.00-7.82 (m, 4H), 7.62-7.47 (m, 3H), 5.38-5.22 (m, 1H) ), 2.55 (d, J = 5.0Hz, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -81.69 (s, 3F), -122.01 (dd, J = 275.9, 7.4Hz, 1F), -129.47 (dd, dd, J = 275.9, 16.7 Hz, 1F).
MS (EI, m / z) 275 [M-H -].
13)2,2,3,3,3−ペンタフルオロ−1,1−ジフェニル−1−プロパノール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:7.62-7.47(m,4H),7.41-7.27(m,6H),2.87(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-77.56(s,3F),-116.94(s,2F)。
MS(EI,m/z)301[M-H−]。
13) 2,2,3,3,3-pentafluoro-1,1-diphenyl-1-propanol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.62-7.47 (m, 4H), 7.41-7.27 (m, 6H), 2.87 (s, 1H).
19 F-NMR (282 MHz, Chloroform-d) δ: -77.56 (s, 3F), -116.94 (s, 2F).
MS (EI, m / z) 301 [M-H -].
14)2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−(トリフルオロメチル)フェニル)−1−プロパノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.75-7.45(m,6H),7.43-7.29(m,3H),2.97(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-63.24(s,3F),-77.45(s,3F),-116.14(d,J=278.8Hz,1F),-117.58(d,J=278.9Hz,1F)。
MS(EI,m/z)369[M-H−]。
14) 2,2,3,3,3-pentafluoro-1-phenyl-1- (4- (trifluoromethyl) phenyl) -1-propanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.75-7.45 (m, 6H), 7.43-7.29 (m, 3H), 2.97 (s, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -63.24 (s, 3F), -77.45 (s, 3F), -116.14 (d, J = 278.8Hz, 1F),- 117.58 (d, J = 278.9 Hz, 1F).
MS (EI, m / z) 369 [M-H -].
15)1−(4−ブロモフェニル)−2,2,3,3,3−ペンタフルオロ−1−フェニル−1−プロパノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.56-7.31(m,9H),2.90(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-77.53(s,3F),-116.44(d,J=279.2Hz,1F),-117.66(d,J=279.2Hz,1F)
MS(EI,m/z)379[M-H−]。
15) 1- (4-Bromophenyl) -2,2,3,3,3-pentafluoro-1-phenyl-1-propanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.56-7.31 (m, 9H), 2.90 (s, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -77.53 (s, 3F), -116.44 (d, J = 279.2Hz, 1F), -117.66 (d, J = 279. 2Hz, 1F)
MS (EI, m / z) 379 [M-H -].
16)1−(4−クロロフェニル)−2,2,3,3,3−ペンタフルオロ−1−フェニル−1−プロパノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.57-7.44(m,4H),7.40-7.28(m,5H),2.90(s,1H)
19F−NMR(282MHz,Chloroform−d)δ:-77.54(s,3F),-116.45(d,J=276.4Hz,1F),-117.65(d,J=276.4Hz,1F)
MS(EI,m/z)335[M-H−]
16) 1- (4-Chlorophenyl) -2,2,3,3,3-pentafluoro-1-phenyl-1-propanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.57-7.44 (m, 4H), 7.40-7.28 (m, 5H), 2.90 (s, 1H)
19 F-NMR (282MHz, Chloroform-d) δ: -77.54 (s, 3F), -116.45 (d, J = 276.4Hz, 1F), -117.65 (d, J = 276. 4Hz, 1F)
MS (EI, m / z) 335 [M-H -]
17)1−(3−クロロフェニル)−2,2,3,3,3−ペンタフルオロ−1−フェニル−1−プロパノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.60-7.50(m,3H),7.45-7.23(m,7H),2.94(s,1H)
19F−NMR(282MHz,Chloroform−d)δ:-77.54(s,3F),-116.40(d,J=276.4Hz,1F),-117.58(d,J=279.2Hz,1F)
MS(EI,m/z)335[M-H−]。
17) 1- (3-Chlorophenyl) -2,2,3,3,3-pentafluoro-1-phenyl-1-propanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.60-7.50 (m, 3H), 7.45-7.23 (m, 7H), 2.94 (s, 1H)
19 F-NMR (282MHz, Chloroform-d) δ: -77.54 (s, 3F), -116.40 (d, J = 276.4Hz, 1F), -117.58 (d, J = 279. 2Hz, 1F)
MS (EI, m / z) 335 [M-H -].
18)2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−フェニル−1−プロパノール:
黄色固体。
1H−NMR(300MHz,Chloroform−d)δ:8.18(d,J=8.4Hz,2H),7.76(d,J=8.8Hz,2H),7.60-7.45(m,2H),7.45-7.28(m,3H),3.16(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-77.07(s,3F),-115.41(d,J=279.1Hz,1F),-117.48(d,J=279.1Hz,1F)。
MS(EI,m/z)346[M-H−]。
18) 2,2,3,3,3-pentafluoro-1- (4-nitrophenyl) -1-phenyl-1-propanol:
Yellow solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 8.18 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 8.8 Hz, 2H), 7.60-7.45 (M, 2H), 7.45-7.28 (m, 3H), 3.16 (s, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -77.07 (s, 3F), -115.41 (d, J = 279.1Hz, 1F), -117.48 (d, J = 279. 1Hz, 1F).
MS (EI, m / z) 346 [M-H -].
19)2,2,3,3,3−ペンタフルオロ−1,1−ジ(ピリジン−2−イル)−1−プロパノール:
白色固体。
1HNMR(300MHz,Chloroform−d)δ:8.64-8.52(m,2H),8.30-8.19(m,2H),7.82-7.69(m,2H),7.57(s,1H),7.33-7.20(m,2H)。
19F−NMR(282MHz,Chloroform−d)δ:-78.37(s,3F),-78.37(s,2F)。
MS(EI,m/z)305[M-H−]。
19) 2,2,3,3,3-pentafluoro-1,1-di (pyridin-2-yl) -1-propanol:
White solid.
1 1 HNMR (300 MHz, Chloroform-d) δ: 8.64-8.52 (m, 2H), 8.30-8.19 (m, 2H), 7.82-7.69 (m, 2H), 7.57 (s, 1H), 7.33-7.20 (m, 2H).
19 F-NMR (282 MHz, Chloroform-d) δ: -78.37 (s, 3F), -78.37 (s, 2F).
MS (EI, m / z) 305 [M-H -].
20)9−(ペンタフルオロエチル)−9H−フルオレン−9−オール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:7.69-7.58(m,4H),7.49-7.39(m,2H),7.36-7.27(m,2H),2.96(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-79.31(s,3F),-122.07(s,2F)。
MS(EI,m/z)299[M-H−]。
20) 9- (Pentafluoroethyl) -9H-Fluorene-9-ol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.69-7.58 (m, 4H), 7.49-7.39 (m, 2H), 7.36-7.27 (m, 2H) ), 2.96 (s, 1H).
19 F-NMR (282 MHz, Chloroform-d) δ: -79.31 (s, 3F), -122.07 (s, 2F).
MS (EI, m / z) 299 [M-H -].
21)3,3,4,4,4−ペンタフルオロ−2−フェニル−2−ブタノール:
国際公開第2018/025429号に記載の目的物3bと同じ化合物であり、
1H−NMR、19F−NMR、MS(EI,m/z)は同じであった。
21) 3,3,4,5,4-Pentafluoro-2-phenyl-2-butanol:
It is the same compound as the object 3b described in International Publication No. 2018/025429, and is the same compound.
1 1 H-NMR, 19 F-NMR, MS (EI, m / z) were the same.
22)3,3,4,4,4−ペンタフルオロ−2−(4−メトキシフェニル)−2−ブタノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.47(d,J=8.4Hz,2H),6.96-6.86(m,2H),3.86-3.78(m,3H),2.42(s,1H),1.80(s,3H)。
19F−NMR(282MHz,Chloroform−d)δ:-78.41(s,3F),-122.11(d,J=276.9Hz,1F),-123.67(d,J=277.0Hz,1F)
MS(EI,m/z)269[M-H−]。
22) 3,3,4,5,4-Pentafluoro-2- (4-methoxyphenyl) -2-butanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.47 (d, J = 8.4 Hz, 2H), 6.96-6.86 (m, 2H), 3.86-3.78 (m) , 3H), 2.42 (s, 1H), 1.80 (s, 3H).
19 F-NMR (282MHz, Chloroform-d) δ: -78.41 (s, 3F), -122.11 (d, J = 276.9Hz, 1F), -123.67 (d, J = 277. 0Hz, 1F)
MS (EI, m / z) 269 [M-H -].
23)2−(4−クロロフェニル)−3,3,4,4,4−ペンタフルオロ−2−ブタノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.50(d,J=8.4Hz,2H),7.40-7.33(m,2H),2.42(s,1H),1.80(s,3H)。
19F−NMR(282MHz,Chloroform−d)δ:-78.28(s,3F),-121.75(d,J=277.7Hz,1F),-123.72(d,J=277.8Hz,1F)
MS(EI,m/z)273[M-H−]
23) 2- (4-Chlorophenyl) -3,3,4,5,4-pentafluoro-2-butanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.50 (d, J = 8.4 Hz, 2H), 7.40-7.33 (m, 2H), 2.42 (s, 1H), 1.80 (s, 3H).
19 F-NMR (282MHz, Chloroform-d) δ: -78.28 (s, 3F), -121.75 (d, J = 277.7Hz, 1F), -123.72 (d, J = 277. 8Hz, 1F)
MS (EI, m / z) 273 [M-H -]
24)2−(3−クロロフェニル)−3,3,4,4,4−ペンタフルオロ−2−ブタノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.58(s,1H),7.47-7.41(m,1H),7.37-7.31(m,2H),2.47(s,1H),1.80(s,3H)。
19F−NMR(282MHz,Chloroform−d)δ:-78.27(s,3F),-121.57(d,J=277.9Hz,1F),-123.53(d,J=278.0Hz,1F)。
MS(EI,m/z)273[M-H−]。
24) 2- (3-Chlorophenyl) -3,3,4,5,4-pentafluoro-2-butanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.58 (s, 1H), 7.47-7.41 (m, 1H), 7.37-7.31 (m, 2H), 2. 47 (s, 1H), 1.80 (s, 3H).
19 F-NMR (282MHz, Chloroform-d) δ: -78.27 (s, 3F), -121.57 (d, J = 277.9Hz, 1F), -123.53 (d, J = 278. 0Hz, 1F).
MS (EI, m / z) 273 [M-H -].
25)2−(4−ブロモフェニル)−3,3,4,4,4−ペンタフルオロ−2−ブタノール:
1H−NMR(300MHz,Chloroform−d)δ:7.56-7.48(m,2H),7.43(d,J=8.0Hz,2H),2.71(s,1H),1.79(s,3H)。
19F−NMR(282MHz,Chloroform−d)δ:-78.34(s,3F),-122.83(d,J=277.8Hz,1F),-123.81(d,J=277.9Hz,1F)。
25) 2- (4-Bromophenyl) -3,3,4,5,4-pentafluoro-2-butanol:
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.56-7.48 (m, 2H), 7.43 (d, J = 8.0 Hz, 2H), 2.71 (s, 1H), 1.79 (s, 3H).
19 F-NMR (282MHz, Chloroform-d) δ: -78.34 (s, 3F), -122.83 (d, J = 277.8Hz, 1F), -123.81 (d, J = 277. 9Hz, 1F).
26)3,3,4,4,4−ペンタフルオロ−2−(p−トルイル)−2−ブタノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.44(d,J=7.5Hz,2H),7.20(d,J=6.6Hz,2H),2.43−2.33(m,4H),1.80(s,3H)。
19F−NMR(282MHz,Chloroform−d)δ:-78.39(s,3F),-122.01(d,J=277.3Hz,1F),-123.55(d,J=276.9Hz,1F)。
MS(EI,m/z)253[M-H−]。
26) 3,3,4,5,4-Pentafluoro-2- (p-toluyl) -2-butanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.44 (d, J = 7.5 Hz, 2H), 7.20 (d, J = 6.6 Hz, 2H), 2.43-2.33 (M, 4H), 1.80 (s, 3H).
19 F-NMR (282MHz, Chloroform-d) δ: -78.39 (s, 3F), -122.01 (d, J = 277.3Hz, 1F), -123.55 (d, J = 276. 9Hz, 1F).
MS (EI, m / z) 253 [M-H -].
27)3,3,4,4,4−ペンタフルオロ−2−(4−(トリフルオロメチル)フェニル)−2−ブタノール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ:7.75-7.61(m,4H),2.51(s,1H),1.84(s,3H)。
19F−NMR(282MHz,Chloroform−d)δ:-63.22(s,3F),-78.34(s,3F),-121.64(d,J=278.4Hz,1F),-123.84(d,J=278.4Hz,1F)。
MS(EI,m/z)307[M-H−]。
27) 3,3,4,5,4-Pentafluoro-2- (4- (trifluoromethyl) phenyl) -2-butanol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.75-7.61 (m, 4H), 2.51 (s, 1H), 1.84 (s, 3H).
19 F-NMR (282MHz, Chloroform-d) δ: -63.22 (s, 3F), -78.34 (s, 3F), -121.64 (d, J = 278.4Hz, 1F),- 123.84 (d, J = 278.4 Hz, 1F).
MS (EI, m / z) 307 [M-H -].
28)3,3,4,4,4−ペンタフルオロ−2−(4−(トリフルオロメトキシ)フェニル)−2−ブタノール:
1H−NMR(300MHz,Chloroform−d)δ:7.60(d,J=8.3Hz,2H),7.23(d,J=9.2Hz,2H),2.41(s,1H),1.82(s,3H)。
19F−NMR(282MHz,Chloroform−d)δ:-58.33(s,3F),-78.37(s,3F),-121.87(d,J=278.1Hz,1F),-123.90(d,J=278.0Hz,1F)。
透明液体。
MS(EI,m/z)323[M-H−]。
28) 3,3,4,5,4-Pentafluoro-2- (4- (trifluoromethoxy) phenyl) -2-butanol:
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.60 (d, J = 8.3 Hz, 2H), 7.23 (d, J = 9.2 Hz, 2H), 2.41 (s, 1H) ), 1.82 (s, 3H).
19 F-NMR (282MHz, Chloroform-d) δ: -58.33 (s, 3F), -78.37 (s, 3F), -121.87 (d, J = 278.1Hz, 1F),- 123.90 (d, J = 278.0 Hz, 1F).
Clear liquid.
MS (EI, m / z) 323 [M-H -].
29)(E)−4,4,5,5,5−ペンタフルオロ−1,3−ジフェニル−1−ペンテン−3−オール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:7.70-7.57(m,2H),7.47-7.25(m,8H),6.85(s,2H),2.72(s,1H)
19F−NMR(282MHz,Chloroform−d)δ:-78.15(s,3F),-121.40(d,J=11.4Hz,2F)
MS(EI,m/z)327[M-H−]。
29) (E) -4,4,5,5,5-pentafluoro-1,3-diphenyl-1-pentene-3-ol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.70-7.57 (m, 2H), 7.47-7.25 (m, 8H), 6.85 (s, 2H), 2. 72 (s, 1H)
19 F-NMR (282MHz, Chloroform-d) δ: -78.15 (s, 3F), -121.40 (d, J = 11.4Hz, 2F)
MS (EI, m / z) 327 [M-H -].
30)(E)−4,4,5,5,5−ペンタフルオロ−1,3−ビス(4−フルオロフェニル)−1−ペンテン−3−オール:
黄色液体。
1H−NMR(300MHz,Chloroform−d)δ:7.70-7.52(m,2H),7.46-7.30(m,2H),7.19-6.94(m,4H),6.87-6.66(m,2H),2.73(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-78.10(s,3F),112.88--113.05(m,1F),-113.44--113.61(m,1F),-121.52(s,2F)。
MS(EI,m/z)363[M-H−]。
30) (E) -4,4,5,5,5-pentafluoro-1,3-bis (4-fluorophenyl) -1-pentene-3-ol:
Yellow liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.70-7.52 (m, 2H), 7.46-7.30 (m, 2H), 7.19-6.94 (m, 4H) ), 6.87-6.66 (m, 2H), 2.73 (s, 1H).
19 F-NMR (282MHz, Chloroform-d) δ: -78.10 (s, 3F), 112.88--113.05 (m, 1F), -113.44--113.61 (m, 1F) ), -121.52 (s, 2F).
MS (EI, m / z) 363 [M-H -].
31)(E)−3−(4−ブロモフェニル)−4,4,5,5,5−ペンタフルオロ−1−フェニル−1−ペンテン−3−オール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:7.57-7.47(m,4H),7.44-7.28(m,5H),6.81(s,2H),2.71(s,1H)
19F−NMR(282MHz,Chloroform−d)δ:-78.08(s,3F),-121.52(s,2F)
MS(EI,m/z)405[M-H−]。
31) (E) -3- (4-Bromophenyl) -4,4,5,5,5-pentafluoro-1-phenyl-1-pentene-3-ol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 7.57-7.47 (m, 4H), 7.44-7.28 (m, 5H), 6.81 (s, 2H), 2. 71 (s, 1H)
19 F-NMR (282MHz, Chloroform-d) δ: -78.08 (s, 3F), -121.52 (s, 2F)
MS (EI, m / z) 405 [M-H -].
32)(E)−4,4,5,5,5−ペンタフルオロ−3−(4−メトキシフェニル)−1−フェニル−1−ペンテン−3−オール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ;7.54(d,J=8.5Hz,2H),7.45-7.22(m,5H),6.91(d,J=8.5Hz,2H),6.83(s,2H),3.80(s,3H),2.74(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-78.11(s,3F),-121.41(s,1F),-121.49(s,1F)。
MS(EI,m/z)357[M-H−]。
32) (E) -4,4,5,5,5-pentafluoro-3- (4-methoxyphenyl) -1-phenyl-1-pentene-3-ol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ; 7.54 (d, J = 8.5 Hz, 2H), 7.45-7.22 (m, 5H), 6.91 (d, J = 8) .5Hz, 2H), 6.83 (s, 2H), 3.80 (s, 3H), 2.74 (s, 1H).
19 F-NMR (282 MHz, Chloroform-d) δ: -78.11 (s, 3F), -121.41 (s, 1F), -121.49 (s, 1F).
MS (EI, m / z) 357 [M-H -].
33)(E)−3−(4−クロロフェニル)−4,4,5,5,5−ペンタフルオロ−1−フェニル−1−ペンテン−3−オール:
透明液体。
1H−NMR(300MHz,Chloroform−d)δ;7.57(d,J=8.1Hz,2H),7.44-7.27(m,7H),6.81(s,2H),2.70(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-78.08(s,3F),-121.51(s,2F)。
MS(EI,m/z)361[M-H−]。
33) (E) -3- (4-chlorophenyl) -4,4,5,5,5-pentafluoro-1-phenyl-1-pentene-3-ol:
Clear liquid.
1 1 H-NMR (300 MHz, Chloroform-d) δ; 7.57 (d, J = 8.1 Hz, 2H), 7.44-7.27 (m, 7H), 6.81 (s, 2H), 2.70 (s, 1H).
19 F-NMR (282 MHz, Chloroform-d) δ: -78.08 (s, 3F), -121.51 (s, 2F).
MS (EI, m / z) 361 [M-H -].
34)(E)−4,4,5,5,5−ペンタフルオロ−3−(4−ニトロフェニル)−1−フェニル−1−ペンテン−3−オール:
白色固体。
1H−NMR(300MHz,Chloroform−d)δ:8.25(d,J=8.5Hz,2H),7.84(d,J=8.5Hz,2H),7.45-7.29(m,5H),6.83(s,2H),2.92(s,1H)。
19F−NMR(282MHz,Chloroform−d)δ:-78.03(s,3F),-121.28(s,1F),-121.46(s,1F)。
MS(EI,m/z)372[M-H−]。
34) (E) -4,4,5,5,5-pentafluoro-3- (4-nitrophenyl) -1-phenyl-1-pentene-3-ol:
White solid.
1 1 H-NMR (300 MHz, Chloroform-d) δ: 8.25 (d, J = 8.5 Hz, 2H), 7.84 (d, J = 8.5 Hz, 2H), 7.45-7.29 (M, 5H), 6.83 (s, 2H), 2.92 (s, 1H).
19 F-NMR (282 MHz, Chloroform-d) δ: -78.03 (s, 3F), -121.28 (s, 1F), -121.46 (s, 1F).
MS (EI, m / z) 372 [M-H -].
Claims (7)
で表されるカルボニル化合物類を、有機溶剤中、多価エーテル類及びカリウムtert−ブトキシドもしくはカリウムヘキサメチルジシラジド存在下、ペンタフルオロエタンと反応させることを特徴とする下記一般式(2)
で表されるペンタフルオロエチル基含有アルコール類の製造方法。 In the following general formula (1)
The following general formula (2) is characterized in that the carbonyl compounds represented by are reacted with pentafluoroethane in the presence of polyvalent ethers and potassium tert-butoxide or potassium hexamethyldisilazide in an organic solvent.
A method for producing a pentafluoroethyl group-containing alcohol represented by.
(式(1)中、R1及びR2は、各々独立して、水素原子、メチル基、置換基を有してもよいフェニル基、又はR1とR2が結合して環を形成してもよく、ただしR1及びR2がともに水素原子であることはない。)
で表されるカルボニル化合物類を、有機溶剤中、多価エーテル類及びカリウムtert−ブトキシドもしくはカリウムヘキサメチルジシラジド存在下、ペンタフルオロエタンと反応させることを特徴とする下記一般式(2)
で表されるペンタフルオロエチル基含有アルコール類の製造方法。 In the general formula (1) according to claim 1,
(In the formula (1), R 1 and R 2 independently form a ring by combining a hydrogen atom, a methyl group, a phenyl group which may have a substituent, or R 1 and R 2 to form a ring. However, both R 1 and R 2 are not hydrogen atoms.)
The following general formula (2) is characterized in that the carbonyl compounds represented by are reacted with pentafluoroethane in the presence of polyvalent ethers and potassium tert-butoxide or potassium hexamethyldisilazide in an organic solvent.
A method for producing a pentafluoroethyl group-containing alcohol represented by.
2,2,3,3,3−ペンタフルオロ−1−(4−(トリフルオロメトキシ)フェニル)−1−プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ヨードフェニル)−1−プロパノール、2,2,3,3,3−ペンタフルオロ−1−フェニル−1−(4−(トリフルオロメチル)フェニル)−1−プロパノール、1−(4−ブロモフェニル)−2,2,3,3,3−ペンタフルオロ−1−フェニル−1−プロパノール、1−(4−クロロフェニル)−2,2,3,3,3−ペンタフルオロ−1−フェニル−1−プロパノール、1−(3−クロロフェニル)−2,2,3,3,3−ペンタフルオロ−1−フェニル−1−プロパノール、2,2,3,3,3−ペンタフルオロ−1−(4−ニトロフェニル)−1−フェニル−1−プロパノール、2,2,3,3,3−ペンタフルオロ−1,1−ジ(ピリジン−2−イル)−1−プロパノール、(E)−4,4,5,5,5−ペンタフルオロ−1,3−ジフェニル−1−ペンテン−3−オール、(E)−4,4,5,5,5−ペンタフルオロ−1,3−ビス(4−フルオロフェニル)−1−ペンテン−3−オール、(E)−3−(4−ブロモフェニル)−4,4,5,5,5−ペンタフルオロ−1−フェニル−1−ペンテン−3−オール、(E)−4,4,5,5,5−ペンタフルオロ−3−(4−メトキシフェニル)−1−フェニル−1−ペンテン−3−オール、(E)−3−(4−クロロフェニル)−4,4,5,5,5−ペンタフルオロ−1−フェニル−1−ペンテン−3−オール、(E)−4,4,5,5,5−ペンタフルオロ−3−(4−ニトロフェニル)−1−フェニル−1−ペンテン−3−オール。 The following pentafluoroethyl group-containing alcohol compounds as intermediates for the production of organic semiconductor materials:
2,2,3,3,3-pentafluoro-1- (4- (trifluoromethoxy) phenyl) -1-propanol, 2,2,3,3,3-pentafluoro-1- (4-iodophenyl) ) -1-propanol, 2,2,3,3,3-pentafluoro-1-phenyl-1- (4- (trifluoromethyl) phenyl) -1-propanol, 1- (4-bromophenyl) -2 , 2,3,3,3-pentafluoro-1-phenyl-1-propanol, 1- (4-chlorophenyl) -2,2,3,3,3-pentafluoro-1-phenyl-1-propanol, 1 -(3-Chlorophenyl) -2,2,3,3,3-pentafluoro-1-phenyl-1-propanol, 2,2,3,3,3-pentafluoro-1- (4-nitrophenyl)- 1-Phenyl-1-propanol, 2,2,3,3,3-pentafluoro-1,1-di (pyridine-2-yl) -1-propanol, (E) -4,4,5,5 5-Pentafluoro-1,3-diphenyl-1-penten-3-ol, (E) -4,4,5,5,5-pentafluoro-1,3-bis (4-fluorophenyl) -1- Penten-3-ol, (E) -3- (4-bromophenyl) -4,4,5,5,5-pentafluoro-1-phenyl-1-penten-3-ol, (E) -4, 4,5,5,5-Pentafluoro-3- (4-methoxyphenyl) -1-phenyl-1-penten-3-ol, (E) -3- (4-chlorophenyl) -4,4,5,5 5,5-Phenylfluoro-1-phenyl-1-penten-3-ol, (E) -4,4,5,5,5-pentafluoro-3- (4-nitrophenyl) -1-phenyl-1 -Penten-3-all.
2−(4−クロロフェニル)−3,3,4,4,4−ペンタフルオロ−2−ブタノール、2−(3−クロロフェニル)−3,3,4,4,4−ペンタフルオロ−2−ブタノール、2−(4−ブロモフェニル)−3,3,4,4,4−ペンタフルオロ−2−ブタノール、3,3,4,4,4−ペンタフルオロ−2−(p−トルイル)−2−ブタノール、3,3,4,4,4−ペンタフルオロ−2−(4−(トリフルオロメチル)フェニル)−2−ブタノール、3,3,4,4,4−ペンタフルオロ−2−(4−(トリフルオロメトキシ)フェニル)−2−ブタノール。 The following pentafluoroethyl group-containing alcohol compounds as intermediates for the production of enzyme activity inhibitors:
2- (4-Chlorophenyl) -3,3,4,5,4-pentafluoro-2-butanol, 2- (3-chlorophenyl) -3,3,4,5,4-pentafluoro-2-butanol, 2- (4-Bromophenyl) -3,3,4,5,4-pentafluoro-2-butanol, 3,3,4,5,4-pentafluoro-2- (p-toluyl) -2-butanol , 3,3,4,5,4-Pentafluoro-2- (4- (trifluoromethyl) phenyl) -2-butanol, 3,3,4,4,4-pentafluoro-2- (4-( Trifluoromethoxy) phenyl) -2-butanol.
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