GB777685A - Polyhydrophenanthrene compounds and their preparation - Google Patents

Polyhydrophenanthrene compounds and their preparation

Info

Publication number
GB777685A
GB777685A GB7710/56A GB771056A GB777685A GB 777685 A GB777685 A GB 777685A GB 7710/56 A GB7710/56 A GB 7710/56A GB 771056 A GB771056 A GB 771056A GB 777685 A GB777685 A GB 777685A
Authority
GB
United Kingdom
Prior art keywords
compound
keto
compounds
dodecahydrophenanthrene
methallyl
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
GB7710/56A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB777685A publication Critical patent/GB777685A/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
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/80—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings
    • C07C59/82—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings the keto group being part of a ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises compounds having the skeleton formul : <FORM:0777685/IV(b)/1> <FORM:0777685/IV(b)/2> <FORM:0777685/IV(b)/3> wherein X represents a keto group (with a double bond in the 8(8a)-position), a ketal or cyclic ketal grouping (with a double bond in the 8a(9)-position) or an enol ether group (with double bonds in the 7(8)- and 8a(9)-positions), and R0 represents an alkyl radical and their preparation. Compounds having the formula 5 are obtained by reducing a compound having the formula: <FORM:0777685/IV(b)/4> with the borohydride of an alkali metal or alkaline earth metal, e.g. with sodium borohydride. Compound 5 is in turn reduced with alkali metal, e.g. lithium, in liquid ammonia to produce compound 4. Alternatively compound 3 may be reduced directly to compound 4 with alkali metal, e.g. sodium or potassium in ethanol or butanol. Compound 4 may be esterified to form compound 6, e.g. with diazomethane or with methyl iodide and potassium carbonate. The compounds are blocked in 7-position in all these reactions, and the resulting products may be subsequently converted to 7-keto compounds by hydrolysis with acid, or by treatment with p-toluene-sulphonic acid in acetone. Examples describe the production of 1-carboxymethylene - 2 - methallyl - 2,4b - dimethyl - 4 - hydroxy - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene and the corresponding 7-keto compound, 1 - carboxymethyl - 2 - methallyl - 2,4b - dimethyl - 4 - hydroxy - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene and the corresponding 7-keto compound and 2-carbomethoxymethyl - 2 - methallyl - 2,4b - dimethyl - 4 - hydroxy - 7 - ethylenedioxy - dodecahydrophenanthrene and the corresponding 7-keto compound. Various stereoisomers of the products in the examples are specified. Specifications 763,208 also is referred to.
GB7710/56A 1952-09-17 1953-09-17 Polyhydrophenanthrene compounds and their preparation Expired GB777685A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US777685XA 1952-09-17 1952-09-17

Publications (1)

Publication Number Publication Date
GB777685A true GB777685A (en) 1957-06-26

Family

ID=22139940

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7710/56A Expired GB777685A (en) 1952-09-17 1953-09-17 Polyhydrophenanthrene compounds and their preparation

Country Status (1)

Country Link
GB (1) GB777685A (en)

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