3-亚甲基异苯并呋喃-1(3H)-酮及其衍生物的合成研究有机化学.pdfVIP

DOI: 10.6023/cjoc201206030 研究简报 有机化学 Chinese Journal of Organic Chemistry NOTE 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 (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) 摘要 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 Synthesis of 3-Methyleneisobenzofuran-1(3H)-one and Their Derivatives Zhang, Jizhen*,a Wu, Jianb Wang, Yazhena Zhao, Dejiana Jia, Hongbina a ( School of Chemistry and Environmental Engineering, Jiangsu Teachers University of Technology, Changzhou 213001) b ( School of Petrochemical Engineering, Changzhou University, Changzhou 213164) Abstract 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 hi