高等学校化学学报 ›› 2013, Vol. 34 ›› Issue (12): 2738-2744.doi: 10.7503/cjcu20130303

• 有机化学 • 上一篇    下一篇

磺化笼型介孔碳催化的1,1-二乙酸酯的选择性合成

郑彦军, 李江, 卢俊金, 贾玉才, 李宝林   

  1. 教育部药用资源与天然药物化学重点实验室, 陕西师范大学化学化工学院, 西安 710062
  • 收稿日期:2013-04-02 出版日期:2013-12-10 发布日期:2013-07-02
  • 作者简介:李宝林,男,博士,教授,博士生导师,主要从事有机药物的催化合成研究. E-mail:baolinli@snnu.edu.cn
  • 基金资助:

    国家自然科学基金(批准号:21272144)资助.

Chemoselective Synthesis of 1,1-Diacetate from Aldehydes Catalyzed by Sulfonated Carbon Nanocage

ZHENG Yan-Jun, LI Jiang, LU Jun-Jin, JIA Yu-Cai, LI Bao-Lin   

  1. Key Laboratory for Medicinal Resources and Natural Pharmaceutical Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China
  • Received:2013-04-02 Online:2013-12-10 Published:2013-07-02

摘要:

以磺化的笼型介孔碳为催化剂温和、高效、高选择性地合成了缩羰基二乙酸酯. 在室温和无溶剂条件下,用磺化的笼型介孔碳作催化剂使醛类化合物与乙酸酐之间在5~12 min内反应生成1,1-二乙酸酯,产率高达89%~98%. 在相同条件下酮类化合物不会发生此反应. 反应后催化剂经过简单的处理即可回收利用,回收利用7次活性无明显降低.

关键词: 1,1-二乙酸酯, 醛基保护, 非均相催化剂, 磺化笼型介孔碳

Abstract:

Acetals are one of the most useful carbonyl protecting groups because of their stability under both neutral and basic media. In addition, acetals can be converted to a variety of other functional groups. Thus, to find a green synthesis method of acetals, the sulfonated carbon nanocage(S-CKT) as a reusable solid acid catalyst was applied to the reaction of aldehydes with acetic anhydride. As a result, a mild and efficient method was developed for the chemoselective preparation of 1,1-diacetates(acylals) from the mixture of aldehydes(2 mmol) and acetic anhydride(5 mmol) catalyzed by S-CKT(30 mg) under room temperature and solvent-free conditions. The reaction takes a shorter time(5—12 min) and gives good to excellent yield(89%—98%). While it is found that ketone doesn't react with acetic anhydride to yield corresponding product under the same conditions. The catalyst was recycled seven times without a distinct loss of activity by simple filtration and washing.

Key words: 1,1-Diacetate, Aldehyde protection, Heterogeneous catalyst, Sulfonated carbon nanocage

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