CN110386855B - 1-卤代二烯及制备它和(9e,11z)-9,11-十六碳二烯基乙酸酯的方法 - Google Patents

1-卤代二烯及制备它和(9e,11z)-9,11-十六碳二烯基乙酸酯的方法 Download PDF

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CN110386855B
CN110386855B CN201910310523.9A CN201910310523A CN110386855B CN 110386855 B CN110386855 B CN 110386855B CN 201910310523 A CN201910310523 A CN 201910310523A CN 110386855 B CN110386855 B CN 110386855B
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halo
chloro
bromo
reaction
tetradecadiene
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CN110386855A (zh
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渡部友博
三宅裕树
金生刚
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Shin Etsu Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • 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
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
    • C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
    • 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
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/02—Magnesium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/04—Chloro-alkenes
    • 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
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CN201910310523.9A 2018-04-18 2019-04-17 1-卤代二烯及制备它和(9e,11z)-9,11-十六碳二烯基乙酸酯的方法 Active CN110386855B (zh)

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JP2018079776A JP7019500B2 (ja) 2018-04-18 2018-04-18 （９ｅ，１１ｚ）－９，１１－ヘキサデカジエニル＝アセテートの製造方法
JP2018-079776 2018-04-18

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CN110386855B true CN110386855B (zh) 2023-03-28

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US (1) US10737999B2 (https=)
EP (1) EP3556742B1 (https=)
JP (1) JP7019500B2 (https=)
CN (1) CN110386855B (https=)
ES (1) ES2890957T3 (https=)
MX (1) MX2019004282A (https=)

Families Citing this family (6)

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Publication number Priority date Publication date Assignee Title
JP7291105B2 (ja) * 2020-06-24 2023-06-14 信越化学工業株式会社 （９ｚ，１１ｅ）－９，１１－ヘキサデカジエナールの製造方法
JP7672362B2 (ja) * 2022-06-03 2025-05-07 信越化学工業株式会社 （４ｚ，６ｅ）－４，６－ウンデカジエニル＝トリメチルアセテート、及びそれからの（５ｚ，７ｅ）－５，７－ドデカジエン化合物の製造方法
CN115466232B (zh) * 2022-10-18 2023-06-20 山西农业大学 (6z,9z)-3,4-环氧十九碳二烯的制备方法
JP2024063756A (ja) * 2022-10-26 2024-05-13 信越化学工業株式会社 共役二重結合を有する有機ハロゲン化合物、そのアセテート化合物及びアルコール化合物の製造方法、並びに該有機ハロゲン化合物を合成する為に使用される化合物
JP2023078114A (ja) * 2023-01-13 2023-06-06 信越化学工業株式会社 分子内シグマトロピー転位反応を利用した共役ジエン化合物の製造方法
JP7825591B2 (ja) * 2023-05-01 2026-03-06 信越化学工業株式会社 １－ハロ－２，６，１４－トリメチルオクタデカン化合物、並びにそれを用いた５，１３，１７－トリメチルアルカン化合物の製造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0241335A1 (en) * 1986-03-19 1987-10-14 Shin-Etsu Chemical Co., Ltd. 1-substituted conjugated alka-(E,Z)-diene compounds and a method for the preparation thereof
JPH03240752A (ja) * 1990-02-16 1991-10-28 Shin Etsu Chem Co Ltd １‐ハロ‐４，６，１０‐ヘキサデカトリエン化合物およびその製造方法
JP2007070276A (ja) * 2005-09-06 2007-03-22 Shin Etsu Chem Co Ltd １−ハロ−ｅ，ｚ−４，６−ヘキサデカジエン及びその製造方法並びにこれを用いた性フェロモン化合物の製造方法
CN103102266A (zh) * 2013-01-27 2013-05-15 昆明博鸿生物科技有限公司 一种9z, 11e-十四碳二烯醇乙酸酯的合成方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0241335A1 (en) * 1986-03-19 1987-10-14 Shin-Etsu Chemical Co., Ltd. 1-substituted conjugated alka-(E,Z)-diene compounds and a method for the preparation thereof
JPH03240752A (ja) * 1990-02-16 1991-10-28 Shin Etsu Chem Co Ltd １‐ハロ‐４，６，１０‐ヘキサデカトリエン化合物およびその製造方法
JP2007070276A (ja) * 2005-09-06 2007-03-22 Shin Etsu Chem Co Ltd １−ハロ−ｅ，ｚ−４，６−ヘキサデカジエン及びその製造方法並びにこれを用いた性フェロモン化合物の製造方法
CN103102266A (zh) * 2013-01-27 2013-05-15 昆明博鸿生物科技有限公司 一种9z, 11e-十四碳二烯醇乙酸酯的合成方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
An efficient and stereoselective synthesis of insect pheromones by way of nickel-catalyzed Grignard reactions. Syntheses of gossyplure and pheromones of Eudia pavonia and Droxophila melanogaster;Jean-Philippe Ducoux, et al.;《Tetrahedron》;19921231;第48卷(第31期);第6403-6412页 *
Effects of additional double bonds on some olefinic moth sex attractants;M. D. Chisholm, et al.;《Journal of Chemical Ecology》;19801231;第6卷(第1期);第203-212页 *

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JP2019189529A (ja) 2019-10-31
JP7019500B2 (ja) 2022-02-15
US10737999B2 (en) 2020-08-11
ES2890957T3 (es) 2022-01-25
EP3556742B1 (en) 2021-07-14
MX2019004282A (es) 2019-10-21
CN110386855A (zh) 2019-10-29
EP3556742A1 (en) 2019-10-23
US20190322614A1 (en) 2019-10-24

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