有机化学 ›› 2004, Vol. 24 ›› Issue (4): 450-453. 上一篇    

研究简报

苯基磺酸官能化分子筛催化合成香豆素类化合物

杨建明, 吕剑*   

  1. 西安近代化学研究所 西安 710065
  • 收稿日期:2003-06-02 修回日期:2003-09-10 接受日期:2003-10-20 发布日期:2022-09-19

Synthesis of Substituted Coumarin Compounds on Phenylsulfonic Acid Functionalized Molecular Sieve

YANG, Jian-Ming, LÜ, Jian*   

  1. Xi'an Institute of Modern Chemistry, Xi'an 710065
  • Received:2003-06-02 Revised:2003-09-10 Accepted:2003-10-20 Published:2022-09-19
  • Contact: *E-mail: lvjian204@263.net; Tel: (029)8291213; Fax: (029)8291213.

在苯基磺酸官能化介孔分子筛催化剂作用下,取代苯酚和乙酰乙酸乙酯经Pechmann缩合反应合成系列取代香豆素类化合物.该催化合成反应具有条件温和、产物容易分离、收率高等优点.考察了不同位置取代羟基对该缩合反应的影响.结果表明,间位羟基有利于香豆素衍生物的生成,提高反应收率,对位羟基次之.证实了该固体酸催化活性位为磺酸Brønsted型质子酸.

关键词: 固体酸, 介孔分子筛, 香豆素, Pechmann缩合

A series of substituted coumarin derivatives were synthesized by Pechmann condensation reactions of substituted phenols with acetacetic ester in the presence of phenylsulfonic acid functionalizedMSU material as a solid acid catalyst. The reaction condition of substituted phenols with acetacetic ester on the catalyst was mild and the products were easilyobtained with high yields. The effects of hydroxyl groups in the different positions of the aromatic ring on the reaction were investigated. The results showedthat the hydroxyl group in the meto-position is favorable to the condensationreaction, and the one in the para-position is less favorable to the reaction. It also demonstrated that the catalytic active site of the solid acid is Brønsted protonic acid.

Key words: solid acid, meso-porous molecular sieve, coumarin, Pechmann condensation