有机化学 ›› 2012, Vol. 32 ›› Issue (12): 2344-2349.DOI: 10.6023/cjoc201206030 上一篇    下一篇

研究简报

3-亚甲基异苯并呋喃-1(3H)-酮及其衍生物的合成研究

张继振a, 吴健b, 王雅珍a, 赵德建a, 贾洪斌a   

  1. a 江苏技术师范学院 化学与环境工程学院 常州 213001;
    b 常州大学石油化工学院 常州 213164
  • 收稿日期:2012-06-30 修回日期:2012-08-30 发布日期:2012-08-31
  • 通讯作者: 张继振 E-mail:zhangjizhen999999@yahoo.com.cn

Synthesis of 3-Methyleneisobenzofuran-1(3H)-one and Their Derivatives

Zhang Jizhena, Wu Jianb, Wang Yazhena, Zhao Dejiana, Jia Hongbina   

  1. a School of Chemistry and Environmental Engineering, Jiangsu Teachers University of Technology, Changzhou 213001;
    b School of Petrochemical Engineering, Changzhou University, Changzhou 213164
  • Received:2012-06-30 Revised:2012-08-30 Published:2012-08-31

以2-乙烯基苯甲酸甲酯及其衍生物为原料, 经过酯水解反应, 随后发生环氧化、环合反应制备了3-羟甲基异苯并呋喃-1(3H)-酮及其衍生物; 再和三溴化磷或者对甲苯磺酰氯发生亲核取代, 最后通过消除反应合成了3-亚甲基异苯并呋喃-1(3H)-酮及其衍生物. 在亲核取代和消除反应中, 对甲苯磺酰氯法比三溴化磷法产率高. 目标产物及其中间体有10个是新化合物. 化合物结构用1H NMR, 13C NMR, MS和IR表征. 目标产物在空气中长期放置没有发生二聚.

关键词: 3-亚甲基异苯并呋喃-1(3H)-酮, 原白头翁素, 衍生物, 合成

Starting from 2-vinylbenzoic acid methyl ester and derivatives, 3-hydroxymethylisobenzofuran-1(3H)-one and derivatives were prepared through hydrolysis of esters, followed by epoxidation with m-chloroperoxybenzoic acid, cyclization reaction catalyzed by p-toluenesulfonic acid; then nucleophilic substitution with phosphorus tribromide or tosyl chloride and elimination reaction, 3-methyleneisobenzofuran-1(3H)-one and their derivatives were synthesized. The yield of tosyl chloride method was higher than phosphorus tribromide method in the nucleophilic substitution and elimination reaction. Ten target products and intermediates are new compounds. Their structures were characterized by 1H NMR, 13C NMR, MS and IR techniques. The target products did not dimerize in air over a few weeks.

Key words: 3-methylereisobenzofuran-1(3H)-one, protoanemonin, derivatives, synthesis