3-亚烷基(亚芳基)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/cjoc201312011 研究简报 有机化学 Chinese Journal of Organic Chemistry NOTE 3-亚烷基(亚芳基)异苯并呋喃-1(3H)-酮及其衍生物的合成研究 郑纯智a 朱星星b 赵德建a 贾洪斌a 张继振*,a (a 江苏理工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 报道了 3-亚烷基(亚芳基)异苯并呋喃-1(3H)-酮及其衍生物的简易而且高效的合成方法. 其特点是原料易得、价 格低廉、反应条件温和、收率高. 该方法以异苯并呋喃-1(3H)-酮(苯酞)及其衍生物为原料, 经过自由基溴代合成了 3- 溴异苯并呋喃-1(3H)-酮及其衍生物, 随后与三苯基膦发生亲核取代反应, 接着在三乙胺的作用下发生消除反应生成 Wittig 试剂, 最后与脂肪族醛或者芳香族醛发生 Wittig 反应得到目标化合物. 目标产物及其中间体有13 个是新化合物. 关键词 3-亚烷基(亚芳基)异苯并呋喃-1(3H)-酮; 衍生物; 季鏻盐; Wittig 反应; 合成 Synthesis of 3-Alkylidene(arylidene)isobenfuran-1(3H)-one and Their Derivatives Zheng, Chunzhia Zhu, Xingxingb Zhao, Dejiana Jia, Hongbina Zhang, Jizhen*,a a ( School of Chemistry and Environmental Engineering, Jiangsu Technology of University, Changzhou 213001) b ( School of Petrochemical Engineering, Changzhou University, Changzhou 213164) Abstract This paper reports a novel and highly efficient synthesis of 3-alkylidene(arylidene)isobenzofuran-1(3H)-one and the corresponding derivatives. The new method is characterized with raw material easy to get, low manufacturing cost, mild reaction conditions and high yields. Isobenzofuran-1(3H)-one (phthalide) and their derivatives were used as starting material. After reacted through free-radical bromination with N-bromobutanimide (NBS), the starting materials were converted to the