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    • 72. 发明授权
    • Alkynyl halide compounds and alkenyl acetate compounds therefrom
    • 炔基卤化合物及其烯基乙酸酯化合物
    • US4391984A
    • 1983-07-05
    • US266614
    • 1981-05-22
    • Toshinobu IshiharaAkira YamamotoKenichi Taguchi
    • Toshinobu IshiharaAkira YamamotoKenichi Taguchi
    • C07C17/26C07C67/10
    • C07C17/2632C07C67/11C07C67/283
    • The invention provides a novel method for the synthetic preparation of an .omega.-haloalkyne compound of the general formula R--C.tbd.C--CH.sub.2).sub.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 .omega.-halo-1-bromoalkyne compound of the formula X--CH.sub.2).sub.n C.tbd.C-Br. The .omega.-haloalkyne compound obtained in the above can be readily converted to the corresponding alkenyl acetate of the formula R--CH.dbd.CH--CH.sub.2).sub.n OCOCH.sub.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.
    • 本发明提供了一种合成制备通式为RC 3BOND C-CH 2)n X的ω-卤代炔化合物的新方法,其中X为卤素原子,R为单价烃基,n为4,5或6 通过格利雅试剂RMgX'与式X-CH 2)nC 3 B C C Br的ω-卤代-1-溴代炔化合物的偶联反应。 上述得到的ω-卤代炔化合物可以容易地转化成式R-CH = CH-CH 2)n OCOCH 3的相应的烯基乙酸酯,首先在Lindlar催化剂的存在下进行乙酰化,然后部分氢化。 特别地,作为有害昆虫的性信息素化合物的7,11-十六碳二烯酸乙酯是从与1-卤代-3-辛烯和1,8-二溴 - 辛烯的格氏试剂开始的相同的合成路线中获得的, 1-辛炔。
    • 74. 发明授权
    • Method for the preparation of cis-nonen-6-yl chloride
    • 顺式六烯丙基氯的制备方法
    • US4355193A
    • 1982-10-19
    • US253061
    • 1981-04-10
    • Akira YamamotoToshinobu IshiharaKenichi Taguchi
    • Akira YamamotoToshinobu IshiharaKenichi Taguchi
    • C07C17/263B01J27/00B01J27/122C07B61/00C07C17/00C07C17/26C07C21/04C07C67/00
    • C07C17/2632
    • 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-al 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.degree. to 40.degree. C.
    • 本发明提供了一种用于合成制备顺式 - 壬烯-6-基氯的新型和有效的方法,其是用于合成例如顺式 - 壬烯-6-基乙酸酯,顺式 - 壬烯-6-基氯化物的有用的中间体化合物, 醇,顺式 - 壬烯-6-al等作为香料,以及称为几种害虫的性信息素化合物的顺式十二碳烯-9-乙酸酯和顺式十四碳烯-11-基乙酸酯。 本发明的方法包括使1-溴-3-氯丙烷与顺式 - 己烯-3-基氯的格氏试剂反应,该顺式己烯-3-基氯是通过平凡的叶醇知道的顺式己烯-3-醇的氯化产物。 该反应优选在四氢呋喃中,在催化剂存在下,其可以是二氯化铜或四氯化铜锂,在0-40℃下进行。