立方烷-1，4-二甲酸二甲酯的合成与表征

摘要

以环戊烯酮为原料，与 N-溴代丁二酰亚胺（ NBS）经取代反应得到4-溴环戊-2-烯酮，再经加成、消除、Diels-Alder反应获得中间体2-溴环戊-2，4-二烯酮的二聚体；所得二聚体在酸性条件下经分子内环化加成反应、Favorskii 重排反应、酯化反应生成目标化合物立方烷-1，4-二甲酸二甲酯，产物纯度为99％，合成总收率约0．7％。酯化反应所用催化剂为强酸性阳离子交换树脂，可重复使用3次。采用红外光谱、核磁共振氢谱及碳谱、元素分析、质谱等对中间体和立方烷-1，4-二甲酸二甲酯进行了结构表征。%By using cyclopent-2-enone as starting material,dimethyl cubane-1,4-dicarboxylate was synthesized with total yield of 0. 7% and purity of 99% via substitution,addition,elimination,Diels-Alder reaction,cycloaddition,Favorskii rearrangement and esterification. The catalyst of esterification was strong acidic cation exchange resin. With the catalyst loading of 2%,it could be used repeatedly three times. The structure of dimethyl cubane-1 ,4-dicarboxylate and dicyclopentadienone were characterized by IR,1 H NMR,13 C NMR,MS,and elemental analysis.