GB1196561A - 4-Oxocyclohexyl-3-Oxocyclopentyl-Alkanes and a process for preparing them - Google Patents

4-Oxocyclohexyl-3-Oxocyclopentyl-Alkanes and a process for preparing them

Info

Publication number
GB1196561A
GB1196561A GB319568A GB319568A GB1196561A GB 1196561 A GB1196561 A GB 1196561A GB 319568 A GB319568 A GB 319568A GB 319568 A GB319568 A GB 319568A GB 1196561 A GB1196561 A GB 1196561A
Authority
GB
United Kingdom
Prior art keywords
methyl
oxocyclohexyl
resulting
cyclohexyl
bis
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
Application number
GB319568A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB1196561A publication Critical patent/GB1196561A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • 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
    • C07C45/59—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 five-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
    • C07C45/64—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 introduction of functional groups containing oxygen only in singly bound form
    • 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
    • C07C45/67—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 isomerisation; by change of size of the carbon skeleton
    • C07C45/673—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 isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,196,561. 4-Oxocyclohexyl-3-oxocyclopentylalkanes. FARBWERKE HOECHST A.G. 22 Jan., 1968 [20 Jan., 1967], No. 3195/68. Heading C2C. Novel 4 - oxocyclohexyl - 3 - oxocyclopentylalkanes of the general formula wherein either R and R 1 are both methyl or R is hydrogen and R 1 is ethyl, are prepared by carboxylic acylation of a 4-hydroxycyclohexyl- 4-oxocyclohexyl)-alkane of the general formula wherein R 2 is hydrogen; oxidation of the resulting 4 - aclyoxycyclohexyl - 4 - oxocyclohexyl - alkane of the second general formula above wherein R 2 is carboxylic acyl, with a compound of hexavalent chromium, followed by hydrolysis, carboxylic acylation and thermal decarboxylation of the resulting 4-hydroxycyclohexyl-alkane dicarboxylic acid of the general formula saponification of the resulting 4-acyloxycyclohexyl-3-oxocyclopentyl-alkane of the general formula wherein Ac is carboxylic acyl; and oxidation of the resulting corresponding 4-hydroxycyclohexyl- 3-oxacyclopentyl-alkane with a metallic oxide. 2 - (1<SP>1</SP> - Methyl - 41 - hydroxycyclohexyl) - 3 - (1<SP>1</SP> - methyl - 4<SP>1</SP>- oxocyclohexyl) - butane is prepared by catalytic hydrogenation of 2,3-bis- (1<SP>1</SP> - methyl - 4<SP>1</SP>,4<SP>1</SP> - ethylenedioxy - cyclohexyl) - buta - 1,3 - diene, reduction of the resulting 2,3 - bis - (1<SP>1</SP> - methyl - 41,41 - ethylenedioxy-cyclohexyl)-but-1-ene with sodium borohydride, esterification of the produced 2,3-bis- (1<SP>1</SP> - methyl - 4<SP>1</SP>,4<SP>1</SP> - ethylenedioxy - cyclohexyl) - butan-1-ol with methanesulphonyl chloride, reduction of the obtained 2,3-bis-(1<SP>1</SP>-methyl- 4<SP>1</SP>,4<SP>1</SP> - ethylenedioxy - cyclohexyl) - butan - 1 - ol methanesulphonic acid ester with lithium aluminium hydride, acid hydrolysis of the resulting 2,3 - bis - (1<SP>1</SP> - methyl - 4<SP>1</SP>.4<SP>1</SP> - ethylenedioxy - cyclohexyl)-butane and partial reduction of the resulting 2,3-bis - (1<SP>1</SP> - methyl - 4<SP>1 </SP>- oxo - cyclohexyl)-butane. Pharmaceutical compositions having androgenic, gestagenic, antiphlogistic and anabolic activity comprise as active ingredient a 4-oxocyclohexyl-3-oxo-cyclopentyl-alkane of the first general formula above in admixture or conjunction with a pharmaceutically suitable carrier.
GB319568A 1967-01-20 1968-01-22 4-Oxocyclohexyl-3-Oxocyclopentyl-Alkanes and a process for preparing them Expired GB1196561A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0051303 1967-01-20

Publications (1)

Publication Number Publication Date
GB1196561A true GB1196561A (en) 1970-07-01

Family

ID=7104507

Family Applications (1)

Application Number Title Priority Date Filing Date
GB319568A Expired GB1196561A (en) 1967-01-20 1968-01-22 4-Oxocyclohexyl-3-Oxocyclopentyl-Alkanes and a process for preparing them

Country Status (6)

Country Link
BE (1) BE709678A (en)
CH (1) CH495934A (en)
DE (1) DE1618352A1 (en)
FR (1) FR1568053A (en)
GB (1) GB1196561A (en)
NL (1) NL6800863A (en)

Also Published As

Publication number Publication date
NL6800863A (en) 1968-07-22
CH495934A (en) 1970-09-15
FR1568053A (en) 1969-05-23
BE709678A (en) 1968-07-22
DE1618352A1 (en) 1970-12-17

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