JPS6239134B2 - - Google Patents
Info
- Publication number
- JPS6239134B2 JPS6239134B2 JP53138929A JP13892978A JPS6239134B2 JP S6239134 B2 JPS6239134 B2 JP S6239134B2 JP 53138929 A JP53138929 A JP 53138929A JP 13892978 A JP13892978 A JP 13892978A JP S6239134 B2 JPS6239134 B2 JP S6239134B2
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- toluene
- solution
- reaction
- hexane
- 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.)
- Expired
Links
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001993 dienes Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- -1 bicyclic compound Chemical class 0.000 claims description 5
- 238000007115 1,4-cycloaddition reaction Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005698 Diels-Alder reaction Methods 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 3
- 238000010485 C−C bond formation reaction Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000011982 enantioselective catalyst Substances 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- DTGKSKDOIYIVQL-NQMVMOMDSA-N (+)-Borneol Natural products C1C[C@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-NQMVMOMDSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- REPVLJRCJUVQFA-BZNPZCIMSA-N (1s,3r,4r,5r)-4,6,6-trimethylbicyclo[3.1.1]heptan-3-ol Chemical compound C1[C@@H](O)[C@H](C)[C@@H]2C(C)(C)[C@H]1C2 REPVLJRCJUVQFA-BZNPZCIMSA-N 0.000 description 1
- SJWFXCIHNDVPSH-MRVPVSSYSA-N (2R)-octan-2-ol Chemical compound CCCCCC[C@@H](C)O SJWFXCIHNDVPSH-MRVPVSSYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229960004873 levomenthol Drugs 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13892978A JPS5566522A (en) | 1978-11-13 | 1978-11-13 | Preparation of optically active bicyclic compounds by asymmetric diels-alder reaction |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13892978A JPS5566522A (en) | 1978-11-13 | 1978-11-13 | Preparation of optically active bicyclic compounds by asymmetric diels-alder reaction |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5566522A JPS5566522A (en) | 1980-05-20 |
| JPS6239134B2 true JPS6239134B2 (ru) | 1987-08-21 |
Family
ID=15233431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13892978A Granted JPS5566522A (en) | 1978-11-13 | 1978-11-13 | Preparation of optically active bicyclic compounds by asymmetric diels-alder reaction |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5566522A (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2072270A1 (en) * | 1991-06-26 | 1992-12-27 | Joseph V. Koleske | Production of unsaturated cycloaliphatic esters and derivatives thereof |
| JP5796762B2 (ja) * | 2010-10-18 | 2015-10-21 | 国立大学法人豊橋技術科学大学 | 光学活性なシクロヘキセン誘導体の製造方法 |
-
1978
- 1978-11-13 JP JP13892978A patent/JPS5566522A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5566522A (en) | 1980-05-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Davies et al. | Scope and stereochemistry of the tandem intramolecular cyclopropanation/Cope rearrangement sequence | |
| JP5622019B2 (ja) | アミノアルコール誘導体塩構造を有する不斉有機分子触媒及び該不斉有機分子触媒を用いた光学活性化合物の製造方法 | |
| FR2658187A1 (fr) | Nouveaux acides alpha-hydroxyles, procede de preparation et leur utilisation. | |
| JPS6239134B2 (ru) | ||
| Brady et al. | The (4+ 2) cycloaddition of ketenes and. beta.-methoxy. alpha.,. beta.-unsaturated ketones: 2-pyranones | |
| JPH0417937B2 (ru) | ||
| Carde et al. | A solid-phase version of the palladium-catalyzed carbonyl allylation by allylic alcohols with SnCl2 | |
| JPH0551345A (ja) | 光学活性３−置換−２−ノルボルナノンの製造法 | |
| US3910958A (en) | Process for preparing arylacetic acids and esters thereof | |
| JP2010229097A (ja) | 新規オキサゾリジン誘導体及び新規オキサゾリジン誘導体塩、並びに該オキサゾリジン誘導体塩を不斉有機分子触媒とした光学活性化合物の製造方法 | |
| EP0528694B1 (en) | Method for producing optically active 3-substituted-2-norbornanones and their intermediates | |
| JP3828154B2 (ja) | トリシクロカルボン酸エステル、その製造法およびそれからなる香料 | |
| JP2586607B2 (ja) | 光学活性アルコールの製造法 | |
| JP4605766B2 (ja) | アルキリデンシクロペンタノン誘導体の製造法 | |
| US3976678A (en) | 2,3-Disubstituted levulinaldehydes | |
| JPH04178350A (ja) | 新規なヒメコガネ（Ａｎｏｍａｌａ ｒｕｆｏｃｕｐｒｅａ）性フェロモンの合成中間体であるメチルエステル及びその製法、並びにこのエステルを用いるヒメコガネ（Ａｎｏｍａｌａ ｒｕｆｏｃｕｐｒｅａ）性フェロモンの製法 | |
| KR100365526B1 (ko) | 바이시클로[3.3.1]노난 구조 화합물의 제조방법 | |
| US6313353B1 (en) | Method for producing an optically active acyloin | |
| US7501539B2 (en) | Process for the preparation of alkylidenecyclopentanone derivatives | |
| JP4064645B2 (ja) | 多置換シクロアルケン類の新規製造法 | |
| JP2743798B2 (ja) | 光学活性化合物の製法 | |
| JPH04305548A (ja) | ハロゲノアリルアルコール誘導体 | |
| JPH0597735A (ja) | 光学活性二級アルコ−ルの製造方法 | |
| JPH0782213A (ja) | 光学活性シクロアルケンカルボラクトン誘導体、その製造法 | |
| JPH0761983B2 (ja) | （１ｒ，２ｓ）―２―アルコキシカルボニル―２―メチルシクロヘキサ―４―エン―１―カルボン酸類の製造法 |