IE38497B1 - Process for preparing a cyclopentenone - Google Patents
Process for preparing a cyclopentenoneInfo
- Publication number
- IE38497B1 IE38497B1 IE2003/73A IE200373A IE38497B1 IE 38497 B1 IE38497 B1 IE 38497B1 IE 2003/73 A IE2003/73 A IE 2003/73A IE 200373 A IE200373 A IE 200373A IE 38497 B1 IE38497 B1 IE 38497B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- hydroxy
- known manner
- dione
- nov
- Prior art date
Links
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- JJWGWDOXXKOHRY-SCSAIBSYSA-N (4R)-4-hydroxycyclopentane-1,3-dione Chemical compound O[C@H]1C(CC(C1)=O)=O JJWGWDOXXKOHRY-SCSAIBSYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001033 ether group Chemical group 0.000 abstract 2
- -1 (substituted)aminoxy Chemical group 0.000 abstract 1
- 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 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1440108 Cyclopentenones WISCONSIN ALUMNI RESEARCH FOUNDATION 9 Nov 1973 [27 Nov 1972] 52220/73 Heading C2C Compounds I in which R is C 1-4 hydrocarbyl or benzyl and Z is a -(CH 2 ) n - group, wherein n is an integer of 1 to 12, the -(CH 2 ) n - group being optionally interrupted in the chain by a double or triple bond, are prepared by (a) reducing in known manner a compound II to give a 4-(R)-hydroxycyclopentane-1,3-dione, (b) reacting the 4-(R)-hydroxy-cyclopentane- 1,3-dione to convert the 1-one into a 1-(substituted)silyloxy, (substituted)aminoxy, ester or ether group in known manner, and (c) reducing the resulting compound in known manner. In step (b) the 3 keto group and/or the 4 hydroxy group may also be converted into ester or ether groups. One of the compounds produced by the process of the invention, namely 1 isopropoxy- 2 - (6<SP>1</SP> - carbomethoxyhexyl) - 4(R)- hydroxy- 1 cyolopenten-3-one has antimicrobial activity.
[GB1440108A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30976672A | 1972-11-27 | 1972-11-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE38497L IE38497L (en) | 1974-05-27 |
| IE38497B1 true IE38497B1 (en) | 1978-03-29 |
Family
ID=23199601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2003/73A IE38497B1 (en) | 1972-11-27 | 1973-11-07 | Process for preparing a cyclopentenone |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5328908B2 (en) |
| AR (1) | AR198543A1 (en) |
| AT (1) | AT330143B (en) |
| AU (1) | AU459800B2 (en) |
| BE (1) | BE807825A (en) |
| BG (1) | BG21204A3 (en) |
| CA (1) | CA1034139A (en) |
| CH (1) | CH599098A5 (en) |
| CS (1) | CS170480B2 (en) |
| DD (1) | DD108516A5 (en) |
| DE (1) | DE2358781C3 (en) |
| ES (1) | ES420855A1 (en) |
| FR (1) | FR2207905B1 (en) |
| GB (1) | GB1440108A (en) |
| HU (1) | HU169638B (en) |
| IE (1) | IE38497B1 (en) |
| IL (1) | IL43597A (en) |
| NL (1) | NL7316147A (en) |
| NO (1) | NO138905C (en) |
| PH (1) | PH10276A (en) |
| PL (1) | PL91162B1 (en) |
| RO (1) | RO63011A (en) |
| SE (1) | SE406462B (en) |
| SU (1) | SU617005A3 (en) |
| ZA (1) | ZA738581B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU529883B2 (en) * | 1978-09-04 | 1983-06-23 | Australian National University, The | Substituted cyclopentenones |
| JPS56159683U (en) * | 1980-04-28 | 1981-11-28 | ||
| JP2696933B2 (en) * | 1987-06-16 | 1998-01-14 | 日産化学工業株式会社 | Substituted cyclic ketones and substituted cyclic enones and methods for their preparation |
| US5227505A (en) * | 1987-06-16 | 1993-07-13 | Nissan Chemical Industries, Ltd. | Substituted cyclic ketones, substituted cyclic enones, and process for producing the same |
| US5254708A (en) * | 1987-06-16 | 1993-10-19 | Nissan Chemical Industries, Ltd. | Substituted cyclic ketones, substituted cyclic enones, and process for producing the same |
| US5231208A (en) * | 1987-06-16 | 1993-07-27 | Nissan Chemical Industries, Ltd. | Substituted cyclic ketones, substituted cyclic enones, and process for producing the same |
-
1973
- 1973-11-07 CA CA185,210A patent/CA1034139A/en not_active Expired
- 1973-11-07 IE IE2003/73A patent/IE38497B1/en unknown
- 1973-11-08 AU AU62283/73A patent/AU459800B2/en not_active Expired
- 1973-11-08 IL IL43597A patent/IL43597A/en unknown
- 1973-11-08 ZA ZA738581A patent/ZA738581B/en unknown
- 1973-11-09 GB GB5222073A patent/GB1440108A/en not_active Expired
- 1973-11-15 PH PH15227A patent/PH10276A/en unknown
- 1973-11-16 AR AR251028A patent/AR198543A1/en active
- 1973-11-20 CH CH1628373A patent/CH599098A5/xx not_active IP Right Cessation
- 1973-11-22 AT AT980073A patent/AT330143B/en not_active IP Right Cessation
- 1973-11-22 JP JP13086973A patent/JPS5328908B2/ja not_active Expired
- 1973-11-26 CS CS8114A patent/CS170480B2/cs unknown
- 1973-11-26 RO RO7300076778A patent/RO63011A/en unknown
- 1973-11-26 NL NL7316147A patent/NL7316147A/xx unknown
- 1973-11-26 SE SE737315982A patent/SE406462B/en unknown
- 1973-11-26 DD DD174893A patent/DD108516A5/en unknown
- 1973-11-26 BE BE138190A patent/BE807825A/en not_active IP Right Cessation
- 1973-11-26 BG BG25076A patent/BG21204A3/xx unknown
- 1973-11-26 SU SU731975423A patent/SU617005A3/en active
- 1973-11-26 FR FR7341997A patent/FR2207905B1/fr not_active Expired
- 1973-11-26 NO NO734495A patent/NO138905C/en unknown
- 1973-11-26 DE DE2358781A patent/DE2358781C3/en not_active Expired
- 1973-11-26 HU HUWI246A patent/HU169638B/hu unknown
- 1973-11-26 PL PL1973166812A patent/PL91162B1/en unknown
- 1973-11-26 ES ES420855A patent/ES420855A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| RO63011A (en) | 1978-05-15 |
| NO138905C (en) | 1978-12-06 |
| DE2358781A1 (en) | 1974-06-12 |
| JPS4982649A (en) | 1974-08-08 |
| DE2358781B2 (en) | 1979-01-25 |
| IL43597A0 (en) | 1974-03-14 |
| JPS5328908B2 (en) | 1978-08-17 |
| FR2207905A1 (en) | 1974-06-21 |
| BG21204A3 (en) | 1976-03-20 |
| DD108516A5 (en) | 1974-09-20 |
| SE406462B (en) | 1979-02-12 |
| CA1034139A (en) | 1978-07-04 |
| ZA738581B (en) | 1974-09-25 |
| FR2207905B1 (en) | 1978-02-24 |
| CH599098A5 (en) | 1978-05-12 |
| PH10276A (en) | 1976-11-03 |
| AR198543A1 (en) | 1974-06-28 |
| GB1440108A (en) | 1976-06-23 |
| DE2358781C3 (en) | 1979-11-08 |
| ATA980073A (en) | 1975-09-15 |
| NO138905B (en) | 1978-08-28 |
| AU6228373A (en) | 1975-04-10 |
| SU617005A3 (en) | 1978-07-25 |
| HU169638B (en) | 1976-12-28 |
| NL7316147A (en) | 1974-05-29 |
| CS170480B2 (en) | 1976-08-27 |
| BE807825A (en) | 1974-03-15 |
| AU459800B2 (en) | 1975-04-10 |
| AT330143B (en) | 1976-06-10 |
| PL91162B1 (en) | 1977-02-28 |
| IE38497L (en) | 1974-05-27 |
| ES420855A1 (en) | 1976-04-01 |
| IL43597A (en) | 1976-09-30 |
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