自然科学版
陕西师范大学学报(自然科学版)
化学与材料科学
硅胶负载磷钼酸催化的Meyer-Schuster重排反应
PDF下载 ()
张琳璟, 张琦*, 次仁旺久,柴永海
(陕西师范大学 化学化工学院,陕西 西安 710119)
张琳璟,女,硕士研究生,研究方向为有机合成。E-mail: 1070981118@qq.com
摘要:
为高效环保地制备重要化工中间体——α,β-不饱和羰基化合物,设计了由硅胶负载磷钼酸催化的Meyer-Schuster重排反应合成此类化合物的新方法。结果表明,以DCE为溶剂,在25或50 ℃的条件下,1 mol% PMA/SiO2能够催化多种二级或三级丙炔醇以良好的产率和较高的立体选择性重排成相应的α,β-不饱和醛、酮或羧酸酯。此方法具有条件温和,操作简便,催化剂便宜易制、对环境友好且可循环使用等特点,可应用于此类化合物的合成中。
关键词:
关键词: 合成方法; 磷钼酸; 负载; Meyer-Schuster重排
收稿日期:
2015-04-22
中图分类号:
O622.5
文献标识码:
A
文章编号:
1672-4291(2016)02-0054-06doi:10.15983/j.cnki.jsnu.2016.02.321
基金项目:
国家自然科学基金青年项目(21302119)
Doi:
Study on Meyer-Schuster rearrangement catalyzed by silicon gel supported phosphomolybdic acid
ZHANG Linjing, ZHANG Qi*, Cirenwangjiu, CHAI Yonghai
(School of Chemistry and Chemical Engineering, Shaanxi Normal University,Xi′an 710119, Shaanxi, China)
Abstract:
α,β-unsaturated compounds are crucial structural units for the synthesis of natural products, pharmaceuticals, and other useful materials. Herein, a green approach to prepare this kind of compounds has been developed through Meyer-Schuster rearrangement using an inexpensive, easy-preparation, environmentally benign and readily recycled silicon gel (SiO2) supported phosphomolybdic acid (PMA) as the catalyst.Under the condition of 1 mol% PMA/SiO2,and solvent as a DCE 25 or 50 ℃, a variety of second and tertiary propargylic alcohols are efficiently transformed into the corresponding α,β-unsaturated aldehydes, ketones or carboxylic esters in a good yield and a high stereo selectivity. The notable features of the method are mild reaction conditions, simple operation, and suitable for large-scale preparations.
KeyWords:
synthetic method; phosphomolybdic acid; load; Meyer-Schuster rearrangement