JPS6032727A - 光学活性アルコ−ルの製造方法 - Google Patents
光学活性アルコ−ルの製造方法Info
- Publication number
- JPS6032727A JPS6032727A JP13921783A JP13921783A JPS6032727A JP S6032727 A JPS6032727 A JP S6032727A JP 13921783 A JP13921783 A JP 13921783A JP 13921783 A JP13921783 A JP 13921783A JP S6032727 A JPS6032727 A JP S6032727A
- Authority
- JP
- Japan
- Prior art keywords
- alcohol
- formula
- optically active
- acetal
- hydrocarbon group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 27
- -1 cyclic acetal Chemical class 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 238000003776 cleavage reaction Methods 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 6
- 150000001241 acetals Chemical class 0.000 claims description 26
- 125000000524 functional group Chemical group 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 abstract description 8
- 230000003287 optical effect Effects 0.000 abstract description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 5
- 230000003647 oxidation Effects 0.000 abstract description 4
- 150000002009 diols Chemical class 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000004678 hydrides Chemical class 0.000 abstract description 2
- GTCCGKPBSJZVRZ-RFZPGFLSSA-N (2r,4r)-pentane-2,4-diol Chemical compound C[C@@H](O)C[C@@H](C)O GTCCGKPBSJZVRZ-RFZPGFLSSA-N 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000012752 auxiliary agent Substances 0.000 description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 description 2
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006359 acetalization reaction Methods 0.000 description 2
- 150000008365 aromatic ketones Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000006894 reductive elimination reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JMSUNAQVHOHLMX-UHFFFAOYSA-N 1-cyclohexylethanol Chemical compound CC(O)C1CCCCC1 JMSUNAQVHOHLMX-UHFFFAOYSA-N 0.000 description 1
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
- ICADMAXOJLUEEB-UHFFFAOYSA-N 1-cyclohexylpentan-1-one Chemical compound CCCCC(=O)C1CCCCC1 ICADMAXOJLUEEB-UHFFFAOYSA-N 0.000 description 1
- HHEPNSXKXOXNQV-UHFFFAOYSA-N 1-naphthalen-1-ylbutan-1-one Chemical compound C1=CC=C2C(C(=O)CCC)=CC=CC2=C1 HHEPNSXKXOXNQV-UHFFFAOYSA-N 0.000 description 1
- QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 1
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- VTZJFPSWNQFPCQ-UHFFFAOYSA-N dibutylaluminum Chemical compound CCCC[Al]CCCC VTZJFPSWNQFPCQ-UHFFFAOYSA-N 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- CPDVHGLWIFENDJ-UHFFFAOYSA-N dihexylalumane Chemical compound C(CCCCC)[AlH]CCCCCC CPDVHGLWIFENDJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- WENNKWXPAWNIOO-UHFFFAOYSA-N undecan-5-one Chemical compound CCCCCCC(=O)CCCC WENNKWXPAWNIOO-UHFFFAOYSA-N 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13921783A JPS6032727A (ja) | 1983-07-29 | 1983-07-29 | 光学活性アルコ−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13921783A JPS6032727A (ja) | 1983-07-29 | 1983-07-29 | 光学活性アルコ−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6032727A true JPS6032727A (ja) | 1985-02-19 |
| JPS6224411B2 JPS6224411B2 (enrdf_load_stackoverflow) | 1987-05-28 |
Family
ID=15240241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13921783A Granted JPS6032727A (ja) | 1983-07-29 | 1983-07-29 | 光学活性アルコ−ルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6032727A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4990694A (en) * | 1989-02-27 | 1991-02-05 | Wako Pure Chemical Industries Ltd. | Optically active dimethyl heptanediols |
| US5136061A (en) * | 1990-06-14 | 1992-08-04 | Asahi Denka Kogyo K.K. | Optically active pentane derivatives and intermediates thereof, and process for manufacturing same |
| US5243096A (en) * | 1990-06-14 | 1993-09-07 | Asahi Denka Kogyo K.K. | Optically active pentane derivatives and intermediates thereof, and process for manufacturing same |
-
1983
- 1983-07-29 JP JP13921783A patent/JPS6032727A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4990694A (en) * | 1989-02-27 | 1991-02-05 | Wako Pure Chemical Industries Ltd. | Optically active dimethyl heptanediols |
| US5136061A (en) * | 1990-06-14 | 1992-08-04 | Asahi Denka Kogyo K.K. | Optically active pentane derivatives and intermediates thereof, and process for manufacturing same |
| US5243096A (en) * | 1990-06-14 | 1993-09-07 | Asahi Denka Kogyo K.K. | Optically active pentane derivatives and intermediates thereof, and process for manufacturing same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6224411B2 (enrdf_load_stackoverflow) | 1987-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0478625B2 (enrdf_load_stackoverflow) | ||
| Ono et al. | A convenient synthesis of trifluoromethylated pyrroles and porphyrins. | |
| Brown et al. | Chiral synthesis VIA organoboranes. 26. An efficient synthesis of isoprenyl derivatives of borane-valuable reagents for the isoprenylboration of aldehydes. A convenient route to both enantiomers of ipsenol and ipsdienol in high optical purity | |
| Maezaki et al. | C 2-Symmetric Bis-sulfoxide: A Novel Chiral Auxiliary for Asymmetric Desymmetrization of Cyclic m eso-1, 2-Diols | |
| Stephenson et al. | Chemistry of 1, 4-diradicals. I. Intermediates in the Norrish type II photocleavage | |
| JPS6032727A (ja) | 光学活性アルコ−ルの製造方法 | |
| CN100354246C (zh) | 制备二(烯酮缩二醇)的方法 | |
| Kaino et al. | Chiral aryl grignard reagents-generation and reactions with carbonyl compounds. | |
| Paleček et al. | Novel and convenient aldolization of methyl 3, 3, 3-trifluoropyruvate using enamines instead of ketones | |
| CN105209436B (zh) | 3-哌啶酮化合物及其作为神经激肽-1(nk1)受体拮抗剂的用途 | |
| Perlikowska et al. | A short synthesis of enantiomeric phytoprostanes B1 Type I | |
| Rinaldi et al. | Synthesis of 1, 2, 3-decanetriol stereoisomers | |
| KR100679115B1 (ko) | 1-알파-히드록시콜레칼시페롤 유도체의 제조방법 | |
| JPS62178537A (ja) | ５−ブロム−１−ペンタナ−ル化合物またはそのアセタ−ル誘導体の製造法 | |
| Fleming et al. | Solvent trapping of photochemically generated pyran-4-one-derived oxyallyls: a convenient cyclopentannulation method | |
| JPH03251577A (ja) | 光学活性スチレンオキシドの立体化学反転法および光学活性グリコール誘導体の製法 | |
| CH621784A5 (enrdf_load_stackoverflow) | ||
| CH645334A5 (fr) | Procede de preparation du dimethyl-2,3 pentene-4 al. | |
| Promo | I. Studies directed towards the synthesis of squamostatin E, an annonaceous acetogenin. II. Alpha-cyano cations in the Diels-Alder reaction | |
| CA1194021A (en) | Heteroprostaglandin derivatives and processes for preparing them | |
| JP2002510324A (ja) | 光学活性５−メチル−２−（１−メチルブチル）−５−プロピル−１，３−ジオキサンの製法 | |
| JPS59118733A (ja) | アンゲリカ酸の製造法 | |
| JPH0499740A (ja) | ２―ヒドロキシ―２，５，５，９―テトラメチルデカリルエタノールの製造法 | |
| JPH02174733A (ja) | ４―ハロ―１，３―ブタンジオールおよび／または３，４―エポキシ―１―ブタノールの製造法 | |
| JPS62209074A (ja) | 新規なスルホンアルコ−ル |