IE35436L - Cyclopentenes. - Google Patents

Cyclopentenes.

Info

Publication number
IE35436L
IE35436L IE710858A IE85871A IE35436L IE 35436 L IE35436 L IE 35436L IE 710858 A IE710858 A IE 710858A IE 85871 A IE85871 A IE 85871A IE 35436 L IE35436 L IE 35436L
Authority
IE
Ireland
Prior art keywords
group
enyl
reacting
formula
dimethylcyclopent
Prior art date
Application number
IE710858A
Other versions
IE35436B1 (en
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of IE35436L publication Critical patent/IE35436L/en
Publication of IE35436B1 publication Critical patent/IE35436B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5428—Acyclic unsaturated phosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • 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
    • C07C403/20—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 carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/573—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/577—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/305—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with sulfur or sulfur-containing compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • 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
    • C07D317/10—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 not condensed with other rings
    • C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

1336324 Cyclopentene derivatives F HOFFMANN-LA ROCHE & CO AG 8 July 1971 [10 July 1970] 32112/71 Heading C2C Novel cyclopentene derivatives of the formula wherein X is CH 3 CO, 1-hydroxyethyl, CH 3 CH 2 or CH 3 , and R<SP>1</SP> is CH 2 OH, alkoxymethylene, aralkoxymethylene, alkanoyloxymethylene, aroyloxymethylene, COOH, alkoxycarbonyl, aralkoxycarbonyl, carbamoyl, mono- or di- (C 1-6 alkyl)-carbamoyl, or a N-heterocyclylcarbonyl group attached to the polyene chain through the carbonyl group, are prepared by cyclizing - cum - dehydrating a 3,7,11,11 - tetramethyl - 10,15 - dioxo -'2,4,6,8 - hexadecatetraenoic acid or alkyl or aralkyl esters thereof, or by reacting phosphonium salts of the formula in which X<SP>11</SP> is CH 2 CO (the carbonyl group of which may be ketalized) or, CH 3 or CH 3 CH 2 , Y is aryl or di-(C 1-6 alkyl)amino and Z is a halogen or hydrosulphate ion with aldehydes of the formula or by reacting aldehydes of the formula with phosphonium salts of the formula and, in any desired sequence, subjecting if desired acids so obtained to esterification or to amidation or after ketalization of any keto group which may be present, to reduction and deketalization, or subjecting if desired esters so obtained to hydrolysis of amidation, or, after ketalization of any keto group which may be present to reduction and deketalization, and, if desired, etherifying alcohols thus obtained from acids or esters, and, if desired, reducing an acetyl group X to the 1-hydroxyethyl group or to the ethyl group. 9 - [2 - (1,1 - Ethylendioxyethyl)- 5,5 - dimethylcyclopent - 1 - enyl] - 3,7 - dimethyl - 2,4,6,8,- nonatetraenoic acid ethyl ester and butyl ester are obtained by reacting (3 - ethoxycarbonyl - 2- methylprop - 2 - enyl) - triphenylphosphonium chloride with 5 - [2 - (1,1 - ethylenedioxyethyl)- 5,5 - dimethylcyclopent - 1 - enyl] - 3 - methyl- 2,4-pentadien-1-al and by reacting {5-[2-(1,1- ethylenedioxy ethyl) - 5,5 - dimethylcyclopent- 1 - enyl] - 3 - methyl - 2,4 - pentadienyl} - triphenylphosphonium bromide with 3-formylcrotonic butyl ester respectively. The above ethyl ester may also be prepared by reacting 5 - [2 - (1,1 - ethylenedioxyethyl) - 5,5 - dimethylcyclopent - 1 - enyl] - 3 - methyl - 2,4 - pentadien - 1 - al, 4 - chloro - 3 - methylcrotonic acid ethyl ester and triphenyl phosphine. Pharmaceutical compositions, suitable for enteral, parenteral or topical administration, contain the above novel cyclopentene derivatives and compatible pharmaceutical carriers. The compounds are used in the treatment of precanceroses, carcinomas, acne and psoriasis. [GB1336324A]
IE858/71A 1970-07-10 1971-07-06 Cyclopentene derivatives and a process for the manufacture thereof IE35436B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1048070A CH544057A (en) 1970-07-10 1970-07-10 Process for the preparation of polyene compounds

Publications (2)

Publication Number Publication Date
IE35436L true IE35436L (en) 1972-01-10
IE35436B1 IE35436B1 (en) 1976-02-18

Family

ID=4363681

Family Applications (1)

Application Number Title Priority Date Filing Date
IE858/71A IE35436B1 (en) 1970-07-10 1971-07-06 Cyclopentene derivatives and a process for the manufacture thereof

Country Status (14)

Country Link
AT (2) AT311935B (en)
BE (1) BE769754A (en)
CA (1) CA978186A (en)
CH (1) CH544057A (en)
DE (1) DE2132032A1 (en)
ES (1) ES393090A1 (en)
FR (1) FR2100887A1 (en)
GB (3) GB1336326A (en)
HU (1) HU162584B (en)
IE (1) IE35436B1 (en)
IL (1) IL37253A (en)
NL (1) NL7109525A (en)
SE (1) SE377560B (en)
ZA (1) ZA714124B (en)

Also Published As

Publication number Publication date
IL37253A (en) 1974-12-31
HU162584B (en) 1973-03-28
CH544057A (en) 1973-11-15
ZA714124B (en) 1972-03-29
ES393090A1 (en) 1973-08-16
SE377560B (en) 1975-07-14
AT311935B (en) 1973-12-10
IE35436B1 (en) 1976-02-18
CA978186A (en) 1975-11-18
GB1336325A (en) 1973-11-07
NL7109525A (en) 1972-01-12
IL37253A0 (en) 1971-10-20
AT316507B (en) 1974-07-10
DE2132032A1 (en) 1972-01-13
BE769754A (en) 1972-01-10
GB1336326A (en) 1973-11-07
GB1336324A (en) 1973-11-07
FR2100887A1 (en) 1972-03-24

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