GB777684A - Polyhydrophenanthrene compounds - Google Patents

Polyhydrophenanthrene compounds

Info

Publication number
GB777684A
GB777684A GB5228/56A GB522856A GB777684A GB 777684 A GB777684 A GB 777684A GB 5228/56 A GB5228/56 A GB 5228/56A GB 522856 A GB522856 A GB 522856A GB 777684 A GB777684 A GB 777684A
Authority
GB
United Kingdom
Prior art keywords
compounds
group
univalent
ethylenedioxy
acid
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
GB5228/56A
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 GB777684A publication Critical patent/GB777684A/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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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:0777684/IV(b)/1> <FORM:0777684/IV(b)/2> <FORM:0777684/IV(b)/3> wherein R is <FORM:0777684/IV(b)/4> or = O, R1 is an unsaturated aliphatic hydrocarbon radical (particularly allyl, methallyl and propargyl), X and Y are hydrogen atoms or univalent aliphatic hydrocarbon groups which may be the same or different and together contain not more than four carbon atoms, Z is a univalent hydrocarbon group, and the 7-position is occupied in I either by a divalent group or a pair of univalent groups and in II by a univalent group, said group(s) being convertible on acid hydrolysis to a single keto group in the 7-position. Specified protecting groups are cyclic ketals (e.g. ethylenedioxy, ethylene hemithioketal, ethylene dithioketal), enol ethers (e.g. ethyl enol ether), and non-cyclic ketals (e.g. dimethyl ketal). The invention also comprises the preparation of compounds I and II and other compounds containing in ring C the structure: <FORM:0777684/IV(b)/5> by reacting the corresponding 1 - ketophenanthrene derivative with an a -brominated lower aliphatic acid ester BrCXYCO2Z in the presence of zinc, followed by hydrolysis under alkaline, neutral or mildly acid conditions, and the preparation of compounds III by acid hydrolysis of compounds I or II. In an example: 2,4b-dimethallyl - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene in dry ether is treated with activated zinc and methyl bromoacetate, and the product decomposed with glacial acetic acid to yield 1-carbomethoxymethyl - 2,4b - dimethyl - 1 - hydroxy - 2-methally - 4 - keto - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene which on acid hydrolysis yields the corresponding 7-keto compound. Specifications 763,204 and 763,208 are referred to.
GB5228/56A 1952-09-05 1953-08-21 Polyhydrophenanthrene compounds Expired GB777684A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US777684XA 1952-09-05 1952-09-05

Publications (1)

Publication Number Publication Date
GB777684A true GB777684A (en) 1957-06-26

Family

ID=22139938

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5228/56A Expired GB777684A (en) 1952-09-05 1953-08-21 Polyhydrophenanthrene compounds

Country Status (1)

Country Link
GB (1) GB777684A (en)

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