Sm-CuI促进芝麻素前体的简易合成

Facile synthesis of sesamin precursor promoted by Sm-CuI

在碘化亚铜和分子筛存在下,以胡椒醛和马来酸酯为起始原料,直接使用金属钐促进一步反应制备了芝麻素双内酯型前体。反应以双加成形式完成,反应过程高效简便,合成方法简单新颖,原料易得。反应体系在无水、室温空气中进行。对反应影响因素进行了探讨,最终在优化条件下,胡椒醛与马来酸二甲酯反应所得芝麻素前体产率可达78%。在此基础上,进一步对其他马来酸酯如马来酸二乙酯、马来酸二丁酯和富马酸二甲酯的反应效果进行了研究对比,取得了预期的实验结果,并对反应机理进行了探讨。

In the presence of cuprous iodide and molecular sieves, piperonal and maleates were transformed to dilactone precursor of sesamin with the direct use of samarium metal. The reaction was completed by double addition forming, and the reaction process was efficient and simple. The synthetic method was simple and novel, and the raw materials were easy to obtain. The reaction was carried out in an anhydrous system under dry air at room temperature. The influencing factors on the reaction were investigated. The sesamin precursor was thus afforded with 78% yield under the reaction conditions of optimization. On this basis, the reaction effects of other maleates such as diethyl maleate, dibutyl maleate and dimethyl fumarate were further studied and compared, the expected experimental results were obtained, and the reaction mechanism was discussed.