GB763204A - Improvements in or relating to polyhydrophenanthrene compounds - Google Patents

Improvements in or relating to polyhydrophenanthrene compounds

Info

Publication number
GB763204A
GB763204A GB23128/53A GB2312853A GB763204A GB 763204 A GB763204 A GB 763204A GB 23128/53 A GB23128/53 A GB 23128/53A GB 2312853 A GB2312853 A GB 2312853A GB 763204 A GB763204 A GB 763204A
Authority
GB
United Kingdom
Prior art keywords
ethylenedioxy
dione
dimethyl
keto
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
GB23128/53A
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 GB763204A publication Critical patent/GB763204A/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
    • 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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises hydrophenanthrene derivatives of the formula <FORM:0763204/IV(b)/1> <FORM:0763204/IV(b)/2> (wherein R represents a hydroxyl or keto group, M represents an unsaturated aliphatic hydrocarbon radical, and which contain in position 7 in I either a divalent radical or a pair of univalent radicals which yield a keto group on acid hydrolysis, and in II a single univalent radical convertible to keto on acid hydrolysis), the corresponding 7-keto compounds of the formula <FORM:0763204/IV(b)/3> and a process for their preparation which comprises reacting a 2 : 4b-dimethyl-4-R-7-di-substituted - 1 : 2 : 3 : 4 : 4a : 4b : 5 : 6 : 7 : 8 : 10 : 10a - dodecahydrophenanthrene - 1 - one or the corresponding 7 - monosubstituted - 1 : 2 : 3 : 4 : 4a : 4b : 5 : 6 : 10 : 10a - decahydrophenanthrene derivative with an unsaturated aliphatic hydrocarbon halide (MX) in the presence of an alkali metal or a metal alkoxide to yield I or II respectively, which on acid hydrolysis give the dione III. Specified groups which may occupy the 7-position are ethylenedioxy, ethylenedithioketal, ethylene hemithioketal, dimethyl ketal and ethyl enol ether. In examples: (1) 2 : 4b-dimethyl - 2 - methallyl - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene-1 : 4-dione is prepared by treating a benzene solution of the corresponding 2 : 4b-dimethyl - 7 - ethylenedioxy - dione with methallyl iodide, and then potassium in t.-butyl alcohol. Two isomeric forms are obtained, separable by chromatography. Hydrolysis of the 7-ethylenedioxy group by refluxing with p-toluene sulphonic acid in acetone yields 2 : 4b-dimethyl - 2 - methallyl - 1,2,3,4,4a,4b,5,6,7,9, 10,10a - dodecahydrophenanthrene - 1 : 4 : 7 - trione. The corresponding 2 - methallyl - 7 ethylenedioxy - 4 - ol - 1 - one, 2 - allyl - 7 - ethylenedioxy - 1 : 4 - dione and 4 - ol - 1 - one, and 2 - propargyl - 7 - ethylenedioxy - 1 : 4 - dione and 4-ol-1-one are similarly prepared, and then hydrolysed to the 7-keto derivatives. Specifications 763,203, 763,206 and 763,208 are referred to.
GB23128/53A 1952-08-26 1953-08-21 Improvements in or relating to polyhydrophenanthrene compounds Expired GB763204A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US763204XA 1952-08-26 1952-08-26

Publications (1)

Publication Number Publication Date
GB763204A true GB763204A (en) 1956-12-12

Family

ID=22131247

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23128/53A Expired GB763204A (en) 1952-08-26 1953-08-21 Improvements in or relating to polyhydrophenanthrene compounds

Country Status (1)

Country Link
GB (1) GB763204A (en)

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