GB777681A - Polyhydrophenanthrene compounds - Google Patents

Polyhydrophenanthrene compounds

Info

Publication number
GB777681A
GB777681A GB23130/53A GB2313053A GB777681A GB 777681 A GB777681 A GB 777681A GB 23130/53 A GB23130/53 A GB 23130/53A GB 2313053 A GB2313053 A GB 2313053A GB 777681 A GB777681 A GB 777681A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
dodecahydrophenanthrene
methallyl
compounds
ethylenedioxy
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
GB23130/53A
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 GB777681A publication Critical patent/GB777681A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the formul : <FORM:0777681/IV(b)/1> <FORM:0777681/IV(b)/2> wherein R is hydroxyl or keto, R1 is an unsaturated aliphatic hydrocarbon radical, and R11 is a substituted or unsubstituted unsaturated aliphatic hydrocarbon radical, and which contain in position 7 in I either a divalent group or a pair of univalent groups which yield a keto group on acid hydrolysis, and in II a single univalent group convertible to keto on acid hydrolysis. The invention also comprises the corresponding 7-keto compounds (III), their preparation by acid hydrolysis of compounds I or II, and a process for the preparation of compounds having in ring C the structure: <FORM:0777681/IV(b)/3> by reacting the corresponding 1-keto compounds with an unsaturated aliphatic metallo-organic compound, and hydrolysing the reaction product. Rings A and B can be substituted by hydroxy, acyloxy, alkyl, ether and ketal groups. Specified groups in the 7-position of compounds I and II are ethylene dioxy, ethylene dithioketal, ethylene hemi-thioketal, dimethyl ketal or 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 (IV) is added to ethoxyacetylene magnesium bromide in benzene and the product decomposed with ice-water, yielding 1-ethoxyethinyl - 2,4b - dimethyl - 2-methallyl - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene - 1 - ol-4-one. Similarly, using a stereoisomer of IV, two stereochemical modifications of the 1-ethoxyethinyl derivative are obtained. (2) 2,4b-dimethyl - 2 - methallyl - 7 - ethylenedioxy-1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene - 1 - one - 4 - ol (V) is treated as in (1) to give the corresponding 1-ethoxyethinyl-1,4-diol. (3) Treatment of V with ethereal allyl magnesium bromide gives the corresponding 1-allyl-1,4-diol, which after acid hydrolysis yields 1 - allyl - 2,4b - dimethyl - 2 - methallyl - 1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene 1,4-diol-7-one. (4) Treatment of IV with lithium or potassium acetylide in liquid ammonia, or with acetylene and potassium in t-butanolbenzene gives 1 - ethinyl - 2,4b - dimethyl - 2-methallyl - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene - 1 - ol- 4 - one. (5) Oxidation of the 1 - allyl - 7-ethylenedioxy - 1,4 - diol obtained in (3), using chromium trioxide-pyridine, produces the corresponding 1-ol-4-one, which is then hydrolysed with acid to 1-allyl-2,4b-dimethyl-2-methallyl-1,2,3,4,4a,4b,5,6,7,9,10,10a - dodecahydrophenanthrene - 1 - ol - 4,7 - dione. Specifications 763,204 and 763,208 are referred to.
GB23130/53A 1952-09-05 1953-08-21 Polyhydrophenanthrene compounds Expired GB777681A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US777681XA 1952-09-05 1952-09-05

Publications (1)

Publication Number Publication Date
GB777681A true GB777681A (en) 1957-06-26

Family

ID=22139935

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23130/53A Expired GB777681A (en) 1952-09-05 1953-08-21 Polyhydrophenanthrene compounds

Country Status (1)

Country Link
GB (1) GB777681A (en)

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