等效剂在合成中的应用研究：Ⅵ.合成二氢茉莉酮的新途径

茉莉酮和二氢茉莉酮是一类名贵的香料,此类化合物的合成一直是人们所关注的问题。已有许多报道,其中包括庚醛、1-硝基庚烷与甲基乙烯基酮进行Michael加成和以硝代甘缩酮与庚醛进行硝-醛缩合制得1,4-二酮,再进行分子内缩合为二氢茉莉酮。这些合成方法,有的对反应条件要求较苛刻,不易操作,有的则反应步骤较多,收率低。最近,白俊才等以甲基乙烯基酮和1-己烯为原料,合成了二氢茉莉酮,此法虽然新颖,但氧硼杂环己烷中间体

STUDIES ON THE APPLICATION OF EQUIVALENTS TO SYNTHESIS—Ⅵ.A NOVEL ROUTE TO THE SYNTHESIS OF DIHYDROJASMONE

A novel route for dihydrojasmone synthesis is reported. The main strategy inolves the nucleophilic substitution using ethyl a-cyanoheptyl carbonate (2) as acyl-anion(RC=O) equivalents to bromide (3) ,following by hydrolysis to give the undecane-2,5-dione (5) which by base cyclization afforded dihydrojasmone (6). The method is simple and carried out in mild reaction conditions.