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GB845819A - Novel polyene compounds and the manufacture and conversion thereof - Google Patents

Novel polyene compounds and the manufacture and conversion thereof

Info

Publication number
GB845819A
GB845819A GB27589/58A GB2758958A GB845819A GB 845819 A GB845819 A GB 845819A GB 27589/58 A GB27589/58 A GB 27589/58A GB 2758958 A GB2758958 A GB 2758958A GB 845819 A GB845819 A GB 845819A
Authority
GB
United Kingdom
Prior art keywords
trimethyl
cyclohexen
yne
manufacture
tridecatetraene
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
GB27589/58A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB845819A publication Critical patent/GB845819A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 1-acylated and 1-alkylated 13-[21,61,61-trimethyl-cyclohexen-11-yl] -2,7,11-trimethyl-1,3,6-trihydroxy-tridecatetraene-1,7,9, 11-yne-41s, 13-[21,61,61-trimethyl-cyclohexen -11-yl]-2,7,11-trimethyl-tridecapentaen-2,6,8,10,12 -yn-4-a1-1 and a process for the manufacture of said 1-acylated or 1-alkylated compounds which comprises condensing acetylene in a metal organic reaction either with 8-[216161-trimethyl-cyclohexen-11-yl]-2, 6-dimethyl-octatrien-2,4,6-a1-1 and condensing the resulting 10-[21, 61, 61-cyclohexen -11-y1]-4,8-dimethyl-decatrien-4,6,8-yne-1-o1-3 with a 3-acyloxy or 3-alkoxy-2-methyl-proper-2-a1-1 or with a 3-acyloxy or 3-alkoxy-2-methyl-propen-2-a1-1 and condensing the resulting 1-acyloxy or 1-alkoxy-2-methyl-3-hydroxy-penten-1-yne-4 with the C19 aldehyde. The 1-acylated and 1-alkylated compounds are transformed to the corresponding 1-aldehyde by means of an acid. Illustrative products of the invention are 13-[21; 61,61-trimethyl-cyclohexen-11-yl]-2,7,11 trimethyl -1-benzoyloxy-3,6-dihydroxy-tridecatetraene-1,7, 9,11-yne-4 and 13-[216161-trimethyl-cyclohexen-11-yl]-2, 7, 11-trimethyl-1-isopropxy-3, 6-dihydroxy-tridecatetraene-1,7,9,11-yne-4.
GB27589/58A 1957-10-18 1958-08-28 Novel polyene compounds and the manufacture and conversion thereof Expired GB845819A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH845819X 1957-10-18

Publications (1)

Publication Number Publication Date
GB845819A true GB845819A (en) 1960-08-24

Family

ID=4541810

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27589/58A Expired GB845819A (en) 1957-10-18 1958-08-28 Novel polyene compounds and the manufacture and conversion thereof

Country Status (1)

Country Link
GB (1) GB845819A (en)

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