GB777682A - Polyhydrophenanthrene compounds - Google Patents

Polyhydrophenanthrene compounds

Info

Publication number
GB777682A
GB777682A GB25760/53A GB2576053A GB777682A GB 777682 A GB777682 A GB 777682A GB 25760/53 A GB25760/53 A GB 25760/53A GB 2576053 A GB2576053 A GB 2576053A GB 777682 A GB777682 A GB 777682A
Authority
GB
United Kingdom
Prior art keywords
methallyl
dimethyl
dodecahydrophenanthrene
ethylenedioxy
keto
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
GB25760/53A
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
Priority to GB25760/53A priority Critical patent/GB777682A/en
Publication of GB777682A publication Critical patent/GB777682A/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
    • 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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds having the formula: <FORM:0777682/IV(b)/1> in which the 7-position is occupied either by a bivalent group convertible to keto by acid hydrolysis or by a pair of univalent groups together convertible to a single keto group by acid hydrolysis; and compounds having the formula: <FORM:0777682/IV(b)/2> in which the 7-position is occupied by a univalent group which is convertible to keto by acid hydrolysis, and in each formula R0 represents a (1) carboalkoxymethylene, (2) carboalkoxymethyl, (3) carboxymethylene or (4) carboxymethyl group, and their preparation as follows: 1 - alkoxyethinyl - 1 - hydroxy - 2 - methallyl - 2,4b - dimethyl - 4 - keto - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene is reacted with dilute mineral acid to produce 1-carboalkoxymethylene - 2 - methallyl - 2,4b - dimethyl - 4 - keto- 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene (compound 2); compound 2 is saponified to produce 1-carboxymethylene - 2 - methallyl - 2,4b - dimethyl - 4-keto - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene (compound 3) which is reduced e.g. with alkali metal in a lower alkanol or in liquid ammonia to produce 1 - carboxymethyl - 2 - methallyl - 2,4b - dimethyl - 4 - hydroxy - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10a-dodecahydrophenanthrene (compound 4); compound 4 is converted to a 1-carboalkoxymethyl - 2 - methallyl - 2,4b - dimethyl - 4 - hydroxy - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene (compound 6) which may be oxidized to 1 - carboalkoxymethyl - 2 - methallyl - 2,4b-dimethyl - 4 - ket - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene (compound 7). Alternatively compound 4 can be reacted with an oxidizing agent to produce 1-carboxymethyl - 2 - methallyl- 2,4b - dimethyl- 4 - keto - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene (compound 8) which is then esterified to form compound 7. Examples disclose the production of 1-carboethoxymethylene - 2 - methallyl - 2,4b - dimethyl - 4 - keto - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene, 1-carboethoxymethylene - 2 - methallyl - 2,4b-dimethyl - 4,7 - diketo - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene, 1 - carboxymethylene - 2 - methallyl - 2,4b - dimethyl - 4,7-diketo - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene, 1 - carboxymethyl - 2-methallyl - 2,4b - dimethyl - 4 - keto - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenenthrene, 1 - carboxymethyl - 2-methallyl - 2,4b - dimethyl - 4 - keto - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenenthrene, 1 - carboxymethyl - 2-methallyl - 2,4b - dimethyl - 4,7 - diketo - 1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene, 1 - carbomethoxymethyl - 2 - methallyl-2,4b - dimethyl - 4 - keto - 7 - ethylenedioxy - 1, - 1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene, 1 - carbomethoxymethyl - 2 - methallyl - 2,4b - 4,7 - diketo - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene and their stereoisomers. Specifications 763,208, 777,681, 777,684 and 777,685 are referred to.
GB25760/53A 1953-09-17 1953-09-17 Polyhydrophenanthrene compounds Expired GB777682A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB25760/53A GB777682A (en) 1953-09-17 1953-09-17 Polyhydrophenanthrene compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB25760/53A GB777682A (en) 1953-09-17 1953-09-17 Polyhydrophenanthrene compounds

Publications (1)

Publication Number Publication Date
GB777682A true GB777682A (en) 1957-06-26

Family

ID=22139936

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25760/53A Expired GB777682A (en) 1953-09-17 1953-09-17 Polyhydrophenanthrene compounds

Country Status (1)

Country Link
GB (1) GB777682A (en)

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