METHOD FOR PRODUCING ASYMMETRIC CONJUGATED DIYNE COMPOUND AND METHOD FOR PRODUCING Z,Z-CONJUGATED DIENE COMPOUND USING THE SAME
申请人:Shin-Etsu Chemical Co., Ltd.
公开号:EP3053906A1
公开(公告)日:2016-08-10
Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C-Z1-Y1 to a coupling reaction with an alkynyl halide (2): Y2-Z2-C≡C-X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y2-Z2-C≡C-C≡C-Z1-Y1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.
本发明提供了一种利用盐酸羟胺的廉价安全替代化合物高效生产不对称共轭二炔的方法,以及一种利用由此获得的不对称共轭二炔化合物生产 Z,Z-共轭二烯化合物的方法。更具体地说,本发明提供了一种生产不对称共轭二炔化合物的方法,该方法包括以下步骤:将端炔化合物 (1)HC≡C-Z1-Y1 与炔基卤化物(2)发生偶联反应:在铜催化剂和碱存在下,在水和有机溶剂中使用硼氢化钠与 Y2-Z2-C≡C-X 进行偶联反应,得到不对称共轭二炔化合物 (3):Y2-Z2-C≡C-C≡C-Z1-Y1。此外,还提供了一种通过还原得到的不对称共轭二炔化合物或类似物来生产 Z,Z-共轭二烯化合物的方法。