GB1419182A - Process for preparing 2-substituted-2-cyclopenten-1-ones - Google Patents
Process for preparing 2-substituted-2-cyclopenten-1-onesInfo
- Publication number
- GB1419182A GB1419182A GB4753874A GB4753874A GB1419182A GB 1419182 A GB1419182 A GB 1419182A GB 4753874 A GB4753874 A GB 4753874A GB 4753874 A GB4753874 A GB 4753874A GB 1419182 A GB1419182 A GB 1419182A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trans
- cyclopenten
- cyclopentene
- oxo
- octenylmagnesium
- 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
- -1 2-substituted-2-cyclopenten-1-ones Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- KDHIOWQSFJTRQG-UHFFFAOYSA-N methyl 7-(5-oxocyclopenten-1-yl)heptanoate Chemical compound COC(=O)CCCCCCC1=CCCC1=O KDHIOWQSFJTRQG-UHFFFAOYSA-N 0.000 abstract 2
- PPWWVHMECVPNBC-UHFFFAOYSA-N 2-[6-(oxiran-2-yl)hexyl]cyclopent-2-en-1-one Chemical compound O=C1CCC=C1CCCCCCC1OC1 PPWWVHMECVPNBC-UHFFFAOYSA-N 0.000 abstract 1
- ZZPUYKVNYPHISS-UHFFFAOYSA-N 2-methoxycyclopent-2-en-1-one Chemical compound COC1=CCCC1=O ZZPUYKVNYPHISS-UHFFFAOYSA-N 0.000 abstract 1
- IJAISRYWNXYCTM-UHFFFAOYSA-N 7-(5-oxocyclopenten-1-yl)heptanal Chemical compound O=CCCCCCCC1=CCCC1=O IJAISRYWNXYCTM-UHFFFAOYSA-N 0.000 abstract 1
- LBOKTHVXIPFAJO-UHFFFAOYSA-N 7-(5-oxocyclopenten-1-yl)heptanoic acid Chemical compound OC(=O)CCCCCCC1=CCCC1=O LBOKTHVXIPFAJO-UHFFFAOYSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- BZKFMUIJRXWWQK-UHFFFAOYSA-N cyclopenten-2-one Natural products O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000026045 iodination Effects 0.000 abstract 1
- 238000006192 iodination reaction Methods 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 150000002901 organomagnesium compounds Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- 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
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Toxicology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Materials Engineering (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/221,058 US4031129A (en) | 1972-01-26 | 1972-01-26 | 15-Deoxy-PGE1 and method for preparing same |
| US25572872A | 1972-05-22 | 1972-05-22 | |
| US29344272A | 1972-09-29 | 1972-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1419182A true GB1419182A (en) | 1975-12-24 |
Family
ID=27396893
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB366073A Expired GB1419181A (en) | 1972-01-26 | 1973-01-24 | Prostaglandins and method for preparing same |
| GB4753974A Expired GB1419183A (en) | 1972-01-26 | 1973-01-24 | Iodo-alkenes |
| GB4753874A Expired GB1419182A (en) | 1972-01-26 | 1973-01-24 | Process for preparing 2-substituted-2-cyclopenten-1-ones |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB366073A Expired GB1419181A (en) | 1972-01-26 | 1973-01-24 | Prostaglandins and method for preparing same |
| GB4753974A Expired GB1419183A (en) | 1972-01-26 | 1973-01-24 | Iodo-alkenes |
Country Status (17)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1018970A (en) * | 1972-10-27 | 1977-10-11 | American Home Products Corporation | 15-substituted prostanoic acids |
| JPS5720305B2 (US20100223739A1-20100909-C00005.png) * | 1973-02-28 | 1982-04-27 | ||
| US4029693A (en) * | 1975-01-20 | 1977-06-14 | The Upjohn Company | 2A,2B-Dihomo-11-deoxy-17(substituted phenyl)-18,19,20-trinor-PGE2 compounds and their corresponding esters |
| US4032561A (en) * | 1975-05-27 | 1977-06-28 | The Upjohn Company | 17-Phenyl-18,19,20-trinor-cis-4,5-didehydro-PGF1.sub.α compounds |
| US4365075A (en) * | 1975-09-17 | 1982-12-21 | The Upjohn Company | ω-Aryl-PGD compounds |
| US4016184A (en) * | 1975-09-17 | 1977-04-05 | The Upjohn Company | 9-Deoxy-9,10-didehydro-PGD1 compounds |
| US4029814A (en) * | 1975-12-29 | 1977-06-14 | The Upjohn Company | Phenyl-substituted prostaglandin-e type analogs |
| US4219662A (en) * | 1977-02-28 | 1980-08-26 | The Upjohn Company | 11-Deoxy-17-phenyl-PGE1 analogs |
| AU529883B2 (en) * | 1978-09-04 | 1983-06-23 | Australian National University, The | Substituted cyclopentenones |
-
0
- BE BE794516D patent/BE794516A/xx unknown
-
1973
- 1973-01-15 IE IE599/76A patent/IE37108B1/xx unknown
- 1973-01-15 IE IE57/73A patent/IE37106B1/xx unknown
- 1973-01-15 CA CA161,270A patent/CA1014092A/en not_active Expired
- 1973-01-15 AU AU51081/73A patent/AU452896B2/en not_active Expired
- 1973-01-17 IL IL49286A patent/IL49286A/en unknown
- 1973-01-17 IL IL41305A patent/IL41305A/en unknown
- 1973-01-17 IL IL49285A patent/IL49285A/en unknown
- 1973-01-24 GB GB366073A patent/GB1419181A/en not_active Expired
- 1973-01-24 GB GB4753974A patent/GB1419183A/en not_active Expired
- 1973-01-24 GB GB4753874A patent/GB1419182A/en not_active Expired
- 1973-01-25 CH CH105573A patent/CH590834A5/xx not_active IP Right Cessation
- 1973-01-25 ES ES410962A patent/ES410962A1/es not_active Expired
- 1973-01-25 FR FR7302607A patent/FR2181693B1/fr not_active Expired
- 1973-01-25 AR AR246283A patent/AR199893A1/es active
- 1973-01-25 DE DE2365513A patent/DE2365513C3/de not_active Expired
- 1973-01-25 CH CH270276A patent/CH578502A5/xx not_active IP Right Cessation
- 1973-01-25 BG BG022528A patent/BG25206A3/xx unknown
- 1973-01-25 RO RO197391055A patent/RO71588A/ro unknown
- 1973-01-25 JP JP999673A patent/JPS5333583B2/ja not_active Expired
- 1973-01-25 BG BG032229A patent/BG25207A3/xx unknown
- 1973-01-25 DD DD179629*A patent/DD113214A5/xx unknown
- 1973-01-25 DE DE2365927*A patent/DE2365927A1/de active Pending
- 1973-01-25 CH CH270376A patent/CH580046A5/xx not_active IP Right Cessation
- 1973-01-25 DD DD168453A patent/DD108069A5/xx unknown
- 1973-01-25 BG BG7300032232A patent/BG25208A3/xx unknown
- 1973-01-25 DD DD179628*A patent/DD112750A5/xx unknown
- 1973-01-25 NL NL737301094A patent/NL153514B/xx unknown
-
1974
- 1974-09-18 AR AR255637A patent/AR200537A1/es active
-
1975
- 1975-01-17 FR FR7501566A patent/FR2272642B1/fr not_active Expired
- 1975-01-17 FR FR7501567A patent/FR2257567B1/fr not_active Expired
- 1975-06-16 ES ES438594A patent/ES438594A1/es not_active Expired
- 1975-06-16 ES ES438595A patent/ES438595A1/es not_active Expired
-
1976
- 1976-01-26 SE SE7600888A patent/SE7600888L/xx unknown
- 1976-01-28 SE SE7600890A patent/SE7600890L/xx unknown
- 1976-01-28 SE SE7600889A patent/SE7600889L/xx unknown
- 1976-03-25 IL IL49286A patent/IL49286A0/xx unknown
- 1976-03-25 IL IL49285A patent/IL49285A0/xx unknown
- 1976-10-08 JP JP51120458A patent/JPS5253840A/ja active Pending
- 1976-10-08 JP JP51120459A patent/JPS5253801A/ja active Pending
-
1977
- 1977-07-20 NL NL7708070A patent/NL7708070A/xx not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |