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    Alkynyl halide compounds and alkenyl acetate compounds therefrom
    2.
    发明公开
    Alkynyl halide compounds and alkenyl acetate compounds therefrom 失效
    烷基铝化合物和乙醇酸乙酯化合物

    公开(公告)号：EP0040829A3

    公开(公告)日：1982-02-03

    申请号：EP81103926

    申请日：1981-05-21

    申请人： Shin-Etsu Chemical Co., Ltd.

    发明人： Ishihara, Toshinobu ,  Yamamoto, Akira ,  Taguchi, Kenichi

    IPC分类号： C07C21/22 ,  C07C17/26 ,  C07C69/145 ,  C07C67/00 ,  A01N37/02

    CPC分类号： C07C17/2632 ,  C07C67/11 ,  C07C67/283 ,  C07C21/22 ,  C07C69/145

    摘要： The invention provides a novel method for the synthetic preparation of an ω-haloalkyne compound of the general formula R-C-C≡C(̵CH 2 )̵ n -X, in which X is a halogen atom, R is a monovalent hydrocarbon group and n is 4, 5 or 6, by the coupling reaction of a Grignard reagent RMgX' and an ω-halo-1-bromoalkyne compound of the formula X(̵CH 2 )̵ n -C≡C-Br. The ω-haloalkyne compound obtained in the above can be readily converted to the corresponding alkenyl acetate of the formula R-CH=CH(̵ CH 2 + n -OCOCH 3 by first acetylating and then partially hydrogenating in the presence of a Lindlar catalyst. In particular, 7, 11-hexadecadienyl acetate, which is a sexual pheromone compound of a noxious insect, is obtained in the same route of synthesis starting with the Grignard reagent of a 1-halo-3-octene and 1- 8-dibromo-1-octyne.

    Method for the preparation of alkyne-1 compounds
    7.
    发明公开
    Method for the preparation of alkyne-1 compounds 失效
    一种用于1-炔化合物的制备方法。

    公开(公告)号：EP0044558A1

    公开(公告)日：1982-01-27

    申请号：EP81105710.8

    申请日：1981-07-20

    申请人： Shin-Etsu Chemical Co., Ltd.

    发明人： Ishihara, Toshinobu ,  Yamamoto, Akira ,  Taguchi, Kenichi

    IPC分类号： C07C11/22 ,  C07C11/28 ,  C07C1/26 ,  C07C1/32 ,  C07B17/00 ,  B01J27/10

    CPC分类号： C07C1/326 ,  C07C2527/122 ,  C07C11/28

    摘要： The invention provides a novel synthetic method for the preparation of an alkyne-1 compound of the general formula R(CH 2 ) n C≡CH, in which R is a monovalent hydrocarbon group and n is an integer of 4, 5 or 6, which compound is useful as an intermediate of various organic compounds or, in particular, of several sexual pheromone compounds of noxious insects expected to give a promising means for the extermination of the insects. The method comprises reacting an ω-bromo-1-alkyne compound of the formula Br(CH 2 ) n C≡CH, e.g. 8-bromo-l-octyne, with a Grignard reagent of the formula RMgX, e.g. cis-3-octenylmagnesium chloride, in tetrahydrofuran, preferably, in the presence of a catalyst which is dilithium copper tetrachloride or lithium copper dichloride.

    Method for the preparation of cis-nonen-6-yl chloride
    8.
    发明公开
    Method for the preparation of cis-nonen-6-yl chloride 失效
    一种制备顺式-6-壬烯ylchlorid过程。

    公开(公告)号：EP0038053A1

    公开(公告)日：1981-10-21

    申请号：EP81102781.2

    申请日：1981-04-10

    申请人： Shin-Etsu Chemical Co., Ltd.

    发明人： Yamamoto, Akira ,  Ishihara, Toshinobu ,  Taguchi, Kenichi

    IPC分类号： C07C21/04 ,  C07C17/26

    CPC分类号： C07C17/2632 ,  C07C21/04

    摘要： The invention provides a novel and efficient method for the synthetic preparation of cis-nonen-6-yl chloride which is a useful intermediate compound for the syntheses of, for example, cis-nonen-6-yl acetate, cis-nonen--6-ol, cis-nonen-6-yl and the like as flavors as well as cis-dodecen-9-yl acetate and cis-tetradecen-11-yl acetate known as sexual pheromone compounds of several noxious insects. The inventive method comprises reacting 1-bromo-3-chloropropane with the Grignard reagent of cis-hexen-3-yl chloride which is a chlorination product of cis-hexen-3-ol known by a trivial name of leaf alcohol. The reaction is preferably carried out in tetrahydrofuran in the presence of a catalyst which may be lithium copper dichloride or dilithium copper tetrachloride at 0 to 40°C.

    Method for the preparation of cis-alkenyl bromide and acetate
    9.
    发明公开
    Method for the preparation of cis-alkenyl bromide and acetate 失效
    Verfahren zur Herstellung von cis-Alkenylbromid und -azetat。

    公开(公告)号：EP0038052A1

    公开(公告)日：1981-10-21

    申请号：EP81102780.4

    申请日：1981-04-10

    申请人： Shin-Etsu Chemical Co., Ltd.

    发明人： Yamamoto, Akira ,  Ishihara, Toshinobu ,  Taguchi, Kenichi

    IPC分类号： C07C21/14 ,  C07C69/145 ,  C07C17/26 ,  C07C67/11

    CPC分类号： C07C17/2632 ,  C07B2200/09 ,  C07C67/11 ,  C07C21/14 ,  C07C69/145

    摘要： A novel and improved synthetic route for the preparation of several kinds of cis-alkenyl acetates of the formula RCH=CHCH 2 CH 2 [CH 2 ] n OCOCH 3 , in which R is an alkyl group having from 1 to 8 carbon atoms and n is a positive integer from 1 to 10, which compounds are known as sexual pheromone compounds of various noxious insects utilizable as a powerful means for the extermination of the insects, is proposed. The inventive method comprises cross coupling reaction of a Grignard reagent of a cis-alken-3-yl chloride of the formula RCH= CHCH 2 CH 2 Cl with an α, ω -dibromoalkane of the formula Br(CH 2 ) n Br to form a cis-alkenyl bromide of the formula RCH=CHCH 2 (CH 2 ) n Br which is further reacted with an alkali metal acetate.

    摘要翻译： 一种用于制备式RCH = CHCH2CH2（CH2）nOCOCH3的几种顺式 - 链烯基乙酸酯的新颖和改进的合成路线，其中R是具有1至8个碳原子的烷基，n是1的正整数 提出了哪种化合物被称为可用作灭虫昆虫的有力手段的各种有害昆虫的性信息素化合物。 本发明的方法包括式RCH = CHCH2CH2Cl的顺式 - 烯-3-基氯与式Br（CH2）nBr的α，ω-二溴烷烃的格利雅试剂的交叉偶联反应，以形成式 式RCH = CHCH2（CH2）nBr，其进一步与碱金属乙酸盐反应。