GB975594A - Substituted octalinones and tetrahydro-indanones of use as intermediates in steroid synthesis - Google Patents

Substituted octalinones and tetrahydro-indanones of use as intermediates in steroid synthesis

Info

Publication number
GB975594A
GB975594A GB40557/60A GB4055760A GB975594A GB 975594 A GB975594 A GB 975594A GB 40557/60 A GB40557/60 A GB 40557/60A GB 4055760 A GB4055760 A GB 4055760A GB 975594 A GB975594 A GB 975594A
Authority
GB
United Kingdom
Prior art keywords
carbonyl
hydroxymethylene
compounds
substituted
methylene
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
GB40557/60A
Inventor
Gordon Alan Hughes
Herchel Smith
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.)
Individual
Original Assignee
Individual
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
Priority claimed from GB32620/59A external-priority patent/GB975593A/en
Priority to GB32620/59A priority Critical patent/GB975593A/en
Priority to GB24847/64A priority patent/GB975592A/en
Priority to DE19601793617 priority patent/DE1793617A1/en
Priority to DE19601443083 priority patent/DE1443083A1/en
Priority to DE19601618942 priority patent/DE1618942B2/en
Priority to DE19601443082D priority patent/DE1443082B1/en
Priority to DE19601793651 priority patent/DE1793651C3/en
Priority to SE9089/60A priority patent/SE305866B/xx
Priority to SE16896/68A priority patent/SE358146B/xx
Priority to SE9087/60A priority patent/SE309981B/xx
Priority to CH1078660A priority patent/CH421947A/en
Priority to CH1078560A priority patent/CH421929A/en
Priority to DK376260AA priority patent/DK127592B/en
Priority to IT16634/60A priority patent/IT1061736B/en
Application filed by Individual filed Critical Individual
Priority to GB40557/60A priority patent/GB975594A/en
Publication of GB975594A publication Critical patent/GB975594A/en
Priority to DK273271AA priority patent/DK128534B/en
Priority to DK273371A priority patent/DK130343B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • 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
    • 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
    • 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
    • C07C45/68—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 increase in the number of carbon atoms
    • 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
    • C07C45/68—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 increase in the number of carbon atoms
    • C07C45/69—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 increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • 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
    • C07C45/68—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 increase in the number of carbon atoms
    • C07C45/72—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 increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • 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
    • C07C45/68—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 increase in the number of carbon atoms
    • C07C45/72—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 increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/73—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 increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
    • 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
    • C07C49/395—Saturated compounds containing a keto group being part of a ring of a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • 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
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

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

Abstract

975,594. Substituted octalinones and tetrahydroindanones. H. SMITH. Dec. 20, 1960 [Sept. 25, 1959(2); Feb. 19, 1960], Nos. 40557/60, 40558/60 and 40559/60. Divided out of 975,593. Heading C2C. The invention comprises compounds of formula wherein Ar is phenyl which may be substituted in the m-position with hydroxy, alkoxy, acyloxy, nitro, amino, acylamino or alkylamino as sole substituent, each R is H or alkyl, R <SP>1</SP> is alkyl, Q is methylene or ethylene, and Y is carbonyl, ketalised carbonyl, hydroxymethylene or acyloxymethylene. The compounds and those in which Ar is more generally phenyl having an unsubstituted ortho-position may be prepared by one of the following methods: (a) (Y=carbonyl) cyclodehydration of a compound of formula (b) (Y=carbonyl) condensation of a compound ArCR 2 CR 2 X (X=Cl, Br or organic sulphonyloxy) with a metal enolate of a ketone of structure. (c) (Y=hydroxymethylene) selective reduction of the corresponding compound wherein Y is carbonyl and (d) (Y=ketalised carbonyl or acyloxymethylene) respectively ketalising or esterifying the corresponding compound wherein Y is carbonyl or hydroxymethylene. In examples, the preparation is described of compounds wherein (1)-(12) Ar is phenyl or m-methoxyphenyl, R<SP>1</SP> is methyl, Y is carbonyl, hydroxymethylene or ethylenedioxymethylene and Q is methylene or ethylene; (13), (14), (16), (17) Ar is m-nitro- or m-aminophenyl, R <SP>1</SP> is methyl, Y is carbonyl or hydroxymethylene and Q is methylene, the amino compounds being obtained by reduction of corresponding nitro compounds; (15), (18) Ar is m-acetaminophenyl, R<SP>1</SP> is methyl, Y is carbonyl or acetoxymethylene by acetylation of the appropriate amino precursors. Specifications 975,591, 975,592, 975,595 and 975,596 also are referred to.
GB40557/60A 1959-09-25 1960-11-25 Substituted octalinones and tetrahydro-indanones of use as intermediates in steroid synthesis Expired GB975594A (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
GB32620/59A GB975593A (en) 1959-09-25 1959-09-25 Substituted phenylhexanones of use as intermediates in steroid synthesis
GB24847/64A GB975592A (en) 1959-09-25 1959-09-25 Diketones
DE19601793617 DE1793617A1 (en) 1959-09-25 1960-09-20 Substituted octalinones and tetrahydroindanones
DE19601443083 DE1443083A1 (en) 1959-09-25 1960-09-20 13-alkyl-1,3,5 (10), 8 (9) - (or 9,11) -gonatetraene and process for their preparation
DE19601618942 DE1618942B2 (en) 1959-09-25 1960-09-20 NEW DIKETONE AND A METHOD FOR THEIR PRODUCTION
DE19601443082D DE1443082B1 (en) 1959-09-25 1960-09-20 Tetracyclic diene ketones
DE19601793651 DE1793651C3 (en) 1959-09-25 1960-09-20 Dicyclic triketones and a process for their preparation
DK376260AA DK127592B (en) 1959-09-25 1960-09-23 Substituted phenylhexanones for use as intermediates in the preparation of gonan derivatives.
SE16896/68A SE358146B (en) 1959-09-25 1960-09-23
SE9089/60A SE305866B (en) 1959-09-25 1960-09-23
SE9087/60A SE309981B (en) 1959-09-25 1960-09-23
CH1078660A CH421947A (en) 1959-09-25 1960-09-23 Process for the production of ketones
CH1078560A CH421929A (en) 1959-09-25 1960-09-23 Process for the preparation of an arylalkanone
IT16634/60A IT1061736B (en) 1959-09-25 1960-09-24 PROCESSES FOR THE PREPARATION OF REPLACED ARIL-ALCHYL KETONES
GB40557/60A GB975594A (en) 1959-09-25 1960-11-25 Substituted octalinones and tetrahydro-indanones of use as intermediates in steroid synthesis
DK273271AA DK128534B (en) 1959-09-25 1971-06-04 13-Alkyl-Δ <1,3,5 (10), 8,14> -17-oxogonapentaenes for use as intermediates in the synthesis of corresponding steroids containing a saturated D-ring or saturated C- and D-rings.
DK273371A DK130343B (en) 1959-09-25 1971-06-04 2-Alkylcyclopentane-1,3-diones for use as intermediates in the preparation of 18-homologated steroids.

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB32620/59A GB975593A (en) 1959-09-25 1959-09-25 Substituted phenylhexanones of use as intermediates in steroid synthesis
GB589760 1960-02-19
GB4055960 1960-11-25
GB4055860 1960-11-25
GB40557/60A GB975594A (en) 1959-09-25 1960-11-25 Substituted octalinones and tetrahydro-indanones of use as intermediates in steroid synthesis

Publications (1)

Publication Number Publication Date
GB975594A true GB975594A (en) 1964-11-18

Family

ID=27515788

Family Applications (1)

Application Number Title Priority Date Filing Date
GB40557/60A Expired GB975594A (en) 1959-09-25 1960-11-25 Substituted octalinones and tetrahydro-indanones of use as intermediates in steroid synthesis

Country Status (4)

Country Link
CH (1) CH421929A (en)
GB (1) GB975594A (en)
IT (1) IT1061736B (en)
SE (1) SE309981B (en)

Also Published As

Publication number Publication date
SE309981B (en) 1969-04-14
IT1061736B (en) 1983-04-30
CH421929A (en) 1966-10-15

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