KR950000637A - 시클로펜테놀 유도체의 제조방법 - Google Patents
시클로펜테놀 유도체의 제조방법 Download PDFInfo
- Publication number
- KR950000637A KR950000637A KR1019940012322A KR19940012322A KR950000637A KR 950000637 A KR950000637 A KR 950000637A KR 1019940012322 A KR1019940012322 A KR 1019940012322A KR 19940012322 A KR19940012322 A KR 19940012322A KR 950000637 A KR950000637 A KR 950000637A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- cyclopentenol
- compound
- formula
- iii
- Prior art date
Links
- NWZXFAYYQNFDCA-UHFFFAOYSA-N cyclopenten-1-ol Chemical class OC1=CCCC1 NWZXFAYYQNFDCA-UHFFFAOYSA-N 0.000 title claims abstract 16
- 238000000034 method Methods 0.000 title claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 8
- 125000006239 protecting group Chemical group 0.000 claims abstract 8
- -1 cyclopentenol compound Chemical class 0.000 claims abstract 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims abstract 3
- 239000003960 organic solvent Substances 0.000 claims abstract 3
- 239000011541 reaction mixture Substances 0.000 claims abstract 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims abstract 3
- 239000011701 zinc Substances 0.000 claims abstract 3
- 229910052725 zinc Inorganic materials 0.000 claims abstract 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 2
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 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 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/06—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- 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
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
하기의 단계 : (ⅰ) 하기식 Ⅱ의 시클로펜테놀은 화합물의 수산기를 보호하여 하기식 Ⅲ으로 표시된 시클로펜테놀온 유도체를 수득하고 ; (ⅱ) 불활성 유기용매중의 아연 및 디브로모메탄 또는 디요오드메탄의 혼합물을 티타늄 테트라클로라이드와 반응시키고 ; (ⅲ) 그결과 얻은 반응혼합물을 시클로펜테놀온 유도체 Ⅲ과 반응시켜 하기식 Ⅳ의 시클로펜테놀 유도체를 수득하고 ; (ⅳ) 하기식 Ⅳ로 표시된 시클로펜테놀 유도체로부터 보호기 A를 제거하여 하기식 Ⅰ의 시클로펜테놀 화합물을 수득하는 것으로 구성된 하기식 Ⅰ로 표시된 시클로펜테놀 화합물의 제조방법.
[식들중, R1는 2－프로페닐기 또는 2－프로피닐기를 나타내며, A는 수산기의 보호기를 나타낸다.]
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- 하기의 단계 : (ⅰ) 하기식 Ⅱ의 시클로펜테놀온 화합물의 수산기를 보호하여 하기식 Ⅲ으로 표시된 시클로펜테놀온 유도체를 수득하고 ; (ⅱ) 불활성 유기용매중의 아연 및 디브로모메탄 또는 디요오드메탄의 혼합물을 티탄늄 테트라클로라이드와 반응시키고 ; (ⅲ) 그결과 얻은 반응혼합물을 시클로펜테놀온 유도체Ⅲ과 반응시켜 하기식 Ⅳ의 시클로펜테놀 유도체를 수득하고 ; (ⅳ) 하기식 Ⅳ로 표시된 시클로펜테놀 유도체로부터 보호기 A를 제거하여 하기식 Ⅰ로 표시된 시클로펜테놀 화합물을 수득하는 것으로 구성된 하기식 Ⅰ의 시클로펜테놀 화합물의 제조방법 :[식들중, R12－프로페닐기 또는 2－프로피닐기를 나타내며, A는 수산기의 보호기를 나타낸다.]
- 하기의 단계 : (ⅰ) 불활성 유기용매중의 아연 및 디브로모메탄 또는 디요오드메탄의 혼합물과 티타늄 테트라클로라이드를 반응시키고 ; (ⅱ) 그 결과 얻은 반응혼합물을 하기식 Ⅲ으로 표시된 시클로펜테놀온 유도체와 반응시키는 것으로 구성된 하기식 Ⅳ로 표시된 시클로펜테놀 유도체의 제조방법 :[식들중, R1과 A는 상기에서 정의된 것과 같다.]
- 제 1 항에 있어서, 시클로펜테놀온 화합물 Ⅱ의 수산기의 보호는 유기염기의 존재하에서 시클로펜테놀온 화합물 Ⅱ을 트리(C1－C6)알킬실릴클로라이드 또는 트리(C1－C5)알킬실릴트리플레이트와 반응시킴으로써 수행되고, 시클로펜테놀 유도체 Ⅳ로부터 보호기 A의 제거는 시클로펜테놀 유도체 Ⅳ를 플루오라이드이온 또는 산과 반응시킴으로써 수행되는 방법.
- 제 1 항에 있어서, 시클로펜테놀온 화합물 Ⅱ의 수산기의 보호는 유기염기의 존재하에서 시클로펜테놀온 화합물 Ⅱ을 α위치에서 (C1－C2)알콕시기로 치환된 (C1－C2)알킬 클로라이드와 반응시킴으로써 수행되고, 시클로펜테놀 유도체 Ⅳ로부터 보호기 A의 제거는 시클로펜테놀 유도체 Ⅳ를 산과 반응시킴으로써 수행되는 방법.
- 제 1 항에 있어서, 시클로펜테놀온 화합물 Ⅱ의 수산기의 보호는 산의 존재하에서 시클로펜테놀온 화합물 Ⅱ을 디히드로푸란 또는 디히드로피란과 반응시킴으로써 수행되고, 시클로펜테놀 유도체 Ⅳ로부터 보호기 A의 제거는 시클로펜테놀 유도체 Ⅳ를 산과 반응시킴으로써 수행되는 방법.
- 하기식 Ⅳ으로 표시된 시클로펜테놀 유도체 :(식중, R1는 2－프로페닐기 또는 2－프로피닐기를 나타내며 ; A는 수산기의 보호기를 나타낸다.)
- 제 6 항에 있어서, R1는 2－프로페닐기 또는 2－프로피닐기를 나타내며 ; A는 트리(C1－C6)알킬실릴기, 2－테트라히드로푸라닐기, 2－테트라히드로피라닐기 또는 α위치에서 (C1－C2)알콕시기로 치환된 (C1－C2)알킬기를 나타내는 시클로펜테놀 유도체.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13329693A JPH06345678A (ja) | 1993-06-03 | 1993-06-03 | シクロペンテノール誘導体の製造法 |
| JP93-133296 | 1993-06-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR950000637A true KR950000637A (ko) | 1995-01-03 |
Family
ID=15101344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019940012322A KR950000637A (ko) | 1993-06-03 | 1994-06-01 | 시클로펜테놀 유도체의 제조방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5550260A (ko) |
| EP (1) | EP0627393A1 (ko) |
| JP (1) | JPH06345678A (ko) |
| KR (1) | KR950000637A (ko) |
| CN (1) | CN1100406A (ko) |
| CA (1) | CA2122768A1 (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7439306B2 (en) * | 2004-11-23 | 2008-10-21 | Exxonmobil Chemical Patents Inc. | Polyethylene blends with improved Vicat softening point |
| CN101597224B (zh) * | 2008-06-03 | 2012-07-25 | 程存照 | 乙基环戊烯醇酮的合成方法 |
| CN107188786B (zh) * | 2017-05-31 | 2021-10-22 | 湖北远大生命科学与技术有限责任公司 | 一种医药中间体光学纯环戊烯醇的制备方法 |
| CN112142582A (zh) * | 2020-09-16 | 2020-12-29 | 上海应用技术大学 | 一种甲基环戊烯醇酮的合成方法 |
| CN114230601B (zh) * | 2021-12-12 | 2023-09-22 | 上海彩迩文生化科技有限公司 | 一种手性烯醇化合物的制备及其应用 |
| CN115093341B (zh) * | 2022-08-02 | 2024-03-08 | 江西省科学院应用化学研究所 | 一种2-环戊烯-1-醇衍生物及其合成方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2455025A1 (fr) * | 1979-04-26 | 1980-11-21 | Roussel Uclaf | Esters de derives de l'allethrolone et d'acides cyclopropane carboxyliques, leurs procedes de preparation et les compositions les renfermant |
| FR2455018A1 (fr) * | 1979-04-26 | 1980-11-21 | Roussel Uclaf | Derives de l'allethrolone et leur procede de preparation |
| JPS56156238A (en) * | 1980-05-07 | 1981-12-02 | Sumitomo Chem Co Ltd | Carboxylic acid ester, its preparation and insecticidal and acaricidal agent containing the same as active component |
-
1993
- 1993-06-03 JP JP13329693A patent/JPH06345678A/ja active Pending
-
1994
- 1994-05-03 CA CA 2122768 patent/CA2122768A1/en not_active Abandoned
- 1994-05-10 EP EP19940107302 patent/EP0627393A1/en not_active Ceased
- 1994-06-01 KR KR1019940012322A patent/KR950000637A/ko not_active Application Discontinuation
- 1994-06-02 CN CN94106209A patent/CN1100406A/zh active Pending
- 1994-06-02 US US08/253,065 patent/US5550260A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0627393A1 (en) | 1994-12-07 |
| JPH06345678A (ja) | 1994-12-20 |
| CN1100406A (zh) | 1995-03-22 |
| US5550260A (en) | 1996-08-27 |
| CA2122768A1 (en) | 1994-12-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR840002400A (ko) | 7-옥사비시클로헵탄 및 7-옥사비시클로헵텐 프로스타글라딘 동족체의 제조방법 | |
| KR950701902A (ko) | 리그난계 화합물의 제조방법(process for producing lignan compound) | |
| KR920701103A (ko) | 개선된 비닐에테르 제조방법 | |
| KR950000637A (ko) | 시클로펜테놀 유도체의 제조방법 | |
| KR860000243A (ko) | 아민유도체의 제조방법 | |
| KR850005845A (ko) | 7-아미노-3-치환된-메틸-3-세펨-4-카복실산 및 그의 저급 알킬실릴 유도체의 제조방법 | |
| US4855469A (en) | Preparation of cycloorganotrisilazanes | |
| KR860008185A (ko) | 페넴 화합물의 제조방법 | |
| EP0414904B1 (en) | Preparation of enol silyl ether compounds | |
| KR940002257A (ko) | 세팔로스포린 중간체의 제조방법 | |
| EP0391415A3 (en) | Naphthalocyanine compounds and production thereof | |
| EP0001870B1 (en) | Process for the preparation of organotin compounds | |
| US4837349A (en) | Tertiary-butyldimethylsilyl carbamate derivative and process for producing the same | |
| KR930023320A (ko) | 이보호된 2,3-히드록시메틸 시클로부탄올의 제조방법 | |
| US4914199A (en) | Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives | |
| KR870003110A (ko) | 카바펜엠 항생제 | |
| US5194627A (en) | N-tert-butyldialkylsilylmaleimide and its manufacture | |
| EP0801057B1 (en) | Process for producing optically active trans-vinyl sulfide alcohols | |
| KR950005785A (ko) | 신규한 불소화 알킬 유도체 및 그의 제조방법 | |
| JPS5612395A (en) | Oxazolinoazetidinone derivative | |
| KR920008050A (ko) | 세펨 화합물, 이의 제조방법 및 항균제 | |
| KR930021618A (ko) | 2-아미노-5-메틸-피리딘의 제조방법 | |
| JPH0325418B2 (ko) | ||
| GB8915392D0 (en) | Process for penems | |
| KR830004311A (ko) | 페니실린 화합물의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E601 | Decision to refuse application |