JPS6265686A

JPS6265686A - 光学活性（ｓ）−２−ハロ−１−フエニルエタノ−ルの製造法

光学活性（ｓ）−２−ハロ−１−フエニルエタノ−ルの製造法

Info

Publication number: JPS6265686A
Authority: JP; Japan
Prior art keywords: genus; phenylethanol; formula; halo; formulas
Prior art date: 1985-09-14
Legal status : Granted

Application number

JP20364385A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0528110B2 (enrdf_load_stackoverflow

Inventor

Ikuo Sawa

沢　郁男

Hidetoshi Kutsuki

久津木　英俊

Natsuki Mori

夏樹森

Junzo Hasegawa

淳三長谷川

Kiyoshi Watanabe

清渡辺

Current Assignee

Kanegafuchi Chemical Industry Co Ltd

Original Assignee

Kanegafuchi Chemical Industry Co Ltd

Priority date

1985-09-14

Filing date

1985-09-14

Publication date

1987-03-24

1985-09-14 Application filed by Kanegafuchi Chemical Industry Co Ltd filed Critical Kanegafuchi Chemical Industry Co Ltd

1985-09-14 Priority to JP20364385A priority Critical patent/JPS6265686A/ja

1986-04-10 Priority to US06/849,985 priority patent/US4857468A/en

1986-04-11 Priority to EP86104993A priority patent/EP0198440B1/en

1986-04-11 Priority to DE8686104993T priority patent/DE3686502T2/de

1987-03-24 Publication of JPS6265686A publication Critical patent/JPS6265686A/ja

1993-04-23 Publication of JPH0528110B2 publication Critical patent/JPH0528110B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 6
244000005700 microbiome Species 0.000 claims abstract description 15
241000223218 Fusarium Species 0.000 claims abstract description 7
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims abstract description 4
241000682855 Aegerita Species 0.000 claims abstract description 4
241000222532 Agrocybe Species 0.000 claims abstract description 4
241000223679 Beauveria Species 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
241000228212 Aspergillus Species 0.000 claims abstract description 3
230000003287 optical effect Effects 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 7
241000228245 Aspergillus niger Species 0.000 claims description 4
241000896533 Gliocladium Species 0.000 claims description 4
241000235395 Mucor Species 0.000 claims description 4
XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 claims description 4
WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 3
241000221778 Fusarium fujikuroi Species 0.000 claims description 3
241000985936 Gymnoascus Species 0.000 claims description 3
241000193596 Nadsonia Species 0.000 claims description 3
241000985510 Penicillium restrictum Species 0.000 claims description 3
241000751139 Beauveria bassiana Species 0.000 claims description 2
241000228143 Penicillium Species 0.000 claims description 2
241001533598 Septoria Species 0.000 claims 2
241001324718 Cylindrocladiella camelliae Species 0.000 claims 1
241001279361 Stachybotrys Species 0.000 claims 1
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 abstract description 8
239000003814 drug Substances 0.000 abstract description 4
241001002480 Chloridium Species 0.000 abstract description 2
241001465754 Metazoa Species 0.000 abstract description 2
239000003905 agrochemical Substances 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 abstract description 2
229940079593 drug Drugs 0.000 abstract description 2
239000002994 raw material Substances 0.000 abstract description 2
241001041322 Arxiella Species 0.000 abstract 1
241001465180 Botrytis Species 0.000 abstract 1
241000122173 Cylindrocladium Species 0.000 abstract 1
241001537207 Flammulina Species 0.000 abstract 1
230000000813 microbial effect Effects 0.000 abstract 1
239000002304 perfume Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 12
230000001580 bacterial effect Effects 0.000 description 7
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
229930006000 Sucrose Natural products 0.000 description 5
IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 5
239000005720 sucrose Substances 0.000 description 5
238000005119 centrifugation Methods 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
235000015097 nutrients Nutrition 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
125000001475 halogen functional group Chemical group 0.000 description 3
238000000034 method Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XWCQSILTDPAWDP-MRVPVSSYSA-N (1s)-2-chloro-1-phenylethanol Chemical compound ClC[C@@H](O)C1=CC=CC=C1 XWCQSILTDPAWDP-MRVPVSSYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
229940041514 candida albicans extract Drugs 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000012138 yeast extract Substances 0.000 description 2
DAHHEUQBMDBSLO-MRVPVSSYSA-N (1s)-2-bromo-1-phenylethanol Chemical compound BrC[C@@H](O)C1=CC=CC=C1 DAHHEUQBMDBSLO-MRVPVSSYSA-N 0.000 description 1
AWMVMTVKBNGEAK-MRVPVSSYSA-N (S)-styrene oxide Chemical compound C1O[C@H]1C1=CC=CC=C1 AWMVMTVKBNGEAK-MRVPVSSYSA-N 0.000 description 1
WAPNOHKVXSQRPX-SPBYTNOZSA-N 1-phenylethanol Chemical group [13CH3][13CH](O)C1=CC=CC=C1 WAPNOHKVXSQRPX-SPBYTNOZSA-N 0.000 description 1
XWCQSILTDPAWDP-UHFFFAOYSA-N 2-chloro-1-phenylethanol Chemical compound ClCC(O)C1=CC=CC=C1 XWCQSILTDPAWDP-UHFFFAOYSA-N 0.000 description 1
241000682842 Aegerita candida Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000033325 Cystofilobasidium macerans Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000223194 Fusarium culmorum Species 0.000 description 1
241001019285 Gliomastix murorum Species 0.000 description 1
241000985907 Gymnoascus reesii Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001236817 Paecilomyces <Clavicipitaceae> Species 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241001524057 Scolecobasidium Species 0.000 description 1
241000052425 Scolecobasidium terreum Species 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
241001279364 Stachybotrys chartarum Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
241001360088 Zymoseptoria tritici Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000005273 aeration Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
-1 bromoacetophenone ( S)-2-bromo-1-phenylethanol Chemical compound 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000012136 culture method Methods 0.000 description 1
238000012258 culturing Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003100 immobilizing effect Effects 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
125000001297 nitrogen containing inorganic group Chemical group 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1
239000011686 zinc sulphate Substances 0.000 description 1
235000009529 zinc sulphate Nutrition 0.000 description 1