ES420855A1 - A METHOD TO PREPARE 4- (R) -HYDROXY-2-CYCLOPENTEN-1-ONA- REPLACED IN POSITION 2. - Google Patents
A METHOD TO PREPARE 4- (R) -HYDROXY-2-CYCLOPENTEN-1-ONA- REPLACED IN POSITION 2.Info
- Publication number
- ES420855A1 ES420855A1 ES420855A ES420855A ES420855A1 ES 420855 A1 ES420855 A1 ES 420855A1 ES 420855 A ES420855 A ES 420855A ES 420855 A ES420855 A ES 420855A ES 420855 A1 ES420855 A1 ES 420855A1
- Authority
- ES
- Spain
- Prior art keywords
- substituted
- enol
- ester
- ether
- hydroxy
- 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
- 238000000034 method Methods 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000006179 O-acylation Effects 0.000 abstract 1
- 238000010934 O-alkylation reaction Methods 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005228 aryl sulfonate group Chemical group 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 150000002084 enol ethers Chemical class 0.000 abstract 1
- 238000005837 enolization reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
-
- 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
-
- 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
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
A method of preparing 2-position-substituted 4 (R) -hydroxy-2-cyclopenten-1-one characterized by: (a) asymmetrically reducing a compound of the formula ** (See formula) ** where R is a hydrocarbon radical containing approximately 1 to 4 carbon atoms, or benzyl, and n is an integer from 1 to 12, to obtain a corresponding 4 (R) -hydroxy-cyclopentane-1,3-dione substituted in position 2; (b) subjecting the dione to enolization, whereby the dione adopts an enol-ether or enol-ester configuration, by means, respectively, of selective O-acylation with compounds of the formulas R'-CO-X or R'-SO2-X where X is I, Cl, Br, O-COR'or -OSO2R' and R'is a group selected from the groups phenyl, benzyl, biphenyl or naphthyl, unsubstituted or substituted by halogen, alcohol or alkoxy, or pivaloyl, isobutyl, alkanyl or alkenyl having from about 1 to 6 carbon atoms, or of selective O-alkylation, under mild alkaline conditions, with compounds of the formula R''X where R'' is a group selected from the saturated or unsaturated alcohol groups having from about 1 to 6 carbon, benzyl, diphenylmethyl or ester of the formula CH2-COOR'''or R''' - CH-COOR''' where R'''is a hydrocarbon radical containing from about 1 to 6 carbon atoms, and X is chlorine, bromine, iodine, or the alcohol-substituted or unsubstituted aryl sulfonate, sulfate or isocyanate radical, whereby acylation or alcoholization of the oxygen atom in position C-1 is preferably favored; (c) separating the desired C-1 substituted enol-ester or ether from the substituted enol-ester or ether at C-3; (d) reducing the separate enol-ester or C-1 substituted ether; and (e) recovering the desired 2-position substituted 4 (R) -hydroxy-2-cyclopenten-1-one from the reduction reaction mixture. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30976672A | 1972-11-27 | 1972-11-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES420855A1 true ES420855A1 (en) | 1976-04-01 |
Family
ID=23199601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES420855A Expired ES420855A1 (en) | 1972-11-27 | 1973-11-26 | A METHOD TO PREPARE 4- (R) -HYDROXY-2-CYCLOPENTEN-1-ONA- REPLACED IN POSITION 2. |
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 | ||
| US5231208A (en) * | 1987-06-16 | 1993-07-27 | Nissan Chemical Industries, Ltd. | Substituted cyclic ketones, substituted cyclic enones, and process for producing the same |
| 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 |
-
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 IL IL43597A patent/IL43597A/en unknown
- 1973-11-08 ZA ZA738581A patent/ZA738581B/en unknown
- 1973-11-08 AU AU62283/73A patent/AU459800B2/en not_active Expired
- 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 BE BE138190A patent/BE807825A/en not_active IP Right Cessation
- 1973-11-26 FR FR7341997A patent/FR2207905B1/fr not_active Expired
- 1973-11-26 ES ES420855A patent/ES420855A1/en not_active Expired
- 1973-11-26 BG BG025076A patent/BG21204A3/en unknown
- 1973-11-26 PL PL1973166812A patent/PL91162B1/en unknown
- 1973-11-26 HU HUWI246A patent/HU169638B/hu unknown
- 1973-11-26 DE DE2358781A patent/DE2358781C3/en not_active Expired
- 1973-11-26 SE SE737315982A patent/SE406462B/en unknown
- 1973-11-26 RO RO7300076778A patent/RO63011A/en unknown
- 1973-11-26 NL NL7316147A patent/NL7316147A/xx unknown
- 1973-11-26 DD DD174893A patent/DD108516A5/en unknown
- 1973-11-26 SU SU731975423A patent/SU617005A3/en active
- 1973-11-26 NO NO734495A patent/NO138905C/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO63011A (en) | 1978-05-15 |
| ATA980073A (en) | 1975-09-15 |
| SE406462B (en) | 1979-02-12 |
| NO138905C (en) | 1978-12-06 |
| GB1440108A (en) | 1976-06-23 |
| ZA738581B (en) | 1974-09-25 |
| FR2207905A1 (en) | 1974-06-21 |
| IL43597A (en) | 1976-09-30 |
| FR2207905B1 (en) | 1978-02-24 |
| DD108516A5 (en) | 1974-09-20 |
| DE2358781B2 (en) | 1979-01-25 |
| NO138905B (en) | 1978-08-28 |
| AU6228373A (en) | 1975-04-10 |
| NL7316147A (en) | 1974-05-29 |
| SU617005A3 (en) | 1978-07-25 |
| AU459800B2 (en) | 1975-04-10 |
| HU169638B (en) | 1976-12-28 |
| IE38497B1 (en) | 1978-03-29 |
| AT330143B (en) | 1976-06-10 |
| JPS4982649A (en) | 1974-08-08 |
| DE2358781C3 (en) | 1979-11-08 |
| PL91162B1 (en) | 1977-02-28 |
| AR198543A1 (en) | 1974-06-28 |
| IL43597A0 (en) | 1974-03-14 |
| PH10276A (en) | 1976-11-03 |
| JPS5328908B2 (en) | 1978-08-17 |
| IE38497L (en) | 1974-05-27 |
| BE807825A (en) | 1974-03-15 |
| CA1034139A (en) | 1978-07-04 |
| BG21204A3 (en) | 1976-03-20 |
| DE2358781A1 (en) | 1974-06-12 |
| CH599098A5 (en) | 1978-05-12 |
| CS170480B2 (en) | 1976-08-27 |
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