GB1241208A - Unsaturated branched-chain hydrocarbon derivatives - Google Patents

Unsaturated branched-chain hydrocarbon derivatives

Info

Publication number
GB1241208A
GB1241208A GB40860/68A GB4086068A GB1241208A GB 1241208 A GB1241208 A GB 1241208A GB 40860/68 A GB40860/68 A GB 40860/68A GB 4086068 A GB4086068 A GB 4086068A GB 1241208 A GB1241208 A GB 1241208A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
alkyl
groups
hydroxy
ethyl
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
GB40860/68A
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.)
Zoecon Corp
Original Assignee
Zoecon Corp
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 Zoecon Corp filed Critical Zoecon Corp
Publication of GB1241208A publication Critical patent/GB1241208A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • 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
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/44—Halogenated unsaturated alcohols containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/20—Oxygen atoms
    • 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

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,241,208. Unsaturated C 12 _ 17 branched-chain hydrocarbon derivatives. ZOECON CORP. 27 Aug., 1968 [8 Sept., 1967], No. 40860/68. Heading C2C. [Also in Division A5] Novel unsaturated C 12 _ 17 branched-chain compounds of the formulµ in which [A] is one of the groups [B] is one of the groups [C] is one of the groups of the formulµ A<SP>1</SP>, A<SP>2</SP> above, [D] is one of the groups of the formulµ B<SP>1</SP> , B<SP>2</SP> above, each of R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP> and R<SP>4</SP> is hydrogen or C 1 _ 5 alkyl, R<SP>10</SP> is one of the groups -COOR<SP>11</SP>, -CH 2 R<SP>12</SP>, -CONR<SP>13</SP>R<SP>14</SP>, -CH 2 NR<SP>13</SP>R<SP>14</SP> or -CH 2 PO(OR<SP>15</SP>) 2 , R<SP>11</SP> is hydrogen, C 1 _ 5 alkyl or an alkali metal cation, R<SP>12</SP> is hydroxy or an ether or carboxylic ester thereof; each of R<SP>13</SP> and R<SP>14</SP> is hydrogen, C 1 _ 5 alkyl, hydroxy-C 1 _ 6 alkyl, C 1 _ 8 alkoxyl- C 1 _ 8 alkyl or phenyl or R<SP>13</SP> and R<SP>14</SP> together complete a pyrrolidino, piperidino, piperazino, morpholino or 4<SP>1</SP>-C 1 _ 5 alkyl-piperazino ring, each of R<SP>15</SP> is C 1 _ 5 alkyl, each of Z<SP>2</SP> and Z<SP>3</SP> is hydrogen or together Z<SP>2</SP> and Z<SP>3</SP> represent a double bond or a group each of W<SP>6</SP> and W<SP>10</SP> is hydrogen or hydroxy provided that W<SP>6</SP> is hydrogen when W<SP>7</SP> is hydrogen and W<SP>10</SP> is hydrogen when W<SP>11</SP> is hydrogen, each of W<SP>61</SP>, W<SP>7</SP>, W<SP>101</SP> and W<SP>11</SP> is hydrogen, hydroxy or an ether of carboxylic ester thereof, each of Z<SP>7</SP> and Z<SP>11</SP> is hydroxy or a ether or carboxylic ester thereof or W<SP>6</SP> and W<SP>7</SP> together represent a double bond or a group >0, >CH 2 , >CCl 2 or >CF 2 or W<SP>10</SP> and W<SP>11</SP> together represent a double bond or a group >O, >CH 2 , >CCl 2 or >CF 2 ; and the acid addition salts of the amines, are prepared by dehydrohalogenation of corresponding halogenated compounds as represented by the following partial structures where C, C<SP>1</SP>, C<SP>2</SP>, C<SP>3</SP> and C<SP>4</SP> represent the C-7<SP>1</SP>, C-5, C-6, C-7 and C-8 carbon atoms, or the C-11<SP>1</SP>, C-9, C-10, C-11, C-12 carbon atoms respectively, R represents R<SP>2</SP> or R<SP>3</SP>, Z represents hydrogen or Z<SP>7</SP> or Z<SP>11,</SP> W represents W<SP>6</SP> or W<SP>61</SP> or W<SP>10</SP> or W<SP>101 </SP>and X represents halogen. When Z or W are other than hydrogen, the partial structures (2) or (7) respectively, cannot be obtained. Also, any hydroxy groups in an α-position to X must be protected by etherification or esterification before dehydrohalogenation to avoid forming the oxirane ring. The protecting groups may be removed after formation of the double bond. The reaction is effected by treatment of the halo compound with at least a molar equivalent of a basic reagent per mol. halogen present, e.g. a tertiary amine, an alkali metal alkoxide, hydroxide, carbonate or halide. The reaction product usually contains a mixture of compounds corresponding to the two or more different modes of hydrogen halide elimination. The compounds can be separated by conventional methods. Specific compounds may be identified by chemical methods, e.g. ozonolysis. Thus, ozonolysis of ethyl 3,11-dimethyl-7- ethyl - 10,11 - oxido - trideca - 6 - enoate and 3,11 - dimethyl - 7 - ethyl - 10,11 - oxidotridec- 7-enoate followed by Zn dust reduction yields a mixture of 6,7-oxido-7-methylnonan-3-one and ethyl 3-methyl-5-formylpentanoate and a mixture of 3,4-oxido-4-methyl-hexanol and ethyl 3-methyl-7-oxononanoate respectively. Examples relate to the preparation of a number of unsaturated acids, esters, amides and amines. The products possess arthropod maturation inhibiting properties (see Division A5).
GB40860/68A 1967-09-08 1968-08-27 Unsaturated branched-chain hydrocarbon derivatives Expired GB1241208A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US66648467A 1967-09-08 1967-09-08

Publications (1)

Publication Number Publication Date
GB1241208A true GB1241208A (en) 1971-08-04

Family

ID=24674281

Family Applications (1)

Application Number Title Priority Date Filing Date
GB40860/68A Expired GB1241208A (en) 1967-09-08 1968-08-27 Unsaturated branched-chain hydrocarbon derivatives

Country Status (2)

Country Link
DE (1) DE1793326A1 (en)
GB (1) GB1241208A (en)

Also Published As

Publication number Publication date
DE1793326A1 (en) 1971-12-16

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