有机化学 ›› 2019, Vol. 39 ›› Issue (5): 1383-1395.DOI: 10.6023/cjoc201812038 上一篇    下一篇

研究论文

碳酸钠促进的羧酸对α,β-不饱和酮的Oxa-Michael加成合成酯

王兴予a, 朱雪庆b, 姜炜a, 高亚茹b   

  1. a 西北工业大学附属中学 西安 710072;
    b 西北大学化学与材料科学学院 西安 710069
  • 收稿日期:2018-12-20 修回日期:2019-01-25 出版日期:2019-05-25 发布日期:2019-02-19
  • 通讯作者: 高亚茹 E-mail:gyaru@nwu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21702162)、陕西省教育厅科学基金(No.17JK0788)资助项目.

Synthesis of Esters via Sodium Carbonate Promoted Oxa-Michael Addition of Acids to α,β-Unsaturated Ketones

Wang Xingyua, Zhu Xueqingb, Jiang Weia, Gao Yarub   

  1. a Middle School Attached to Northwestern Polytechnical University, Xi'an 710072;
    b Department of Chemistry & Materials Science, Northwest University, Xi'an 710069
  • Received:2018-12-20 Revised:2019-01-25 Online:2019-05-25 Published:2019-02-19
  • Contact: 10.6023/cjoc201812038 E-mail:gyaru@nwu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21702162), and the Scientific Research Program Funded by Shaanxi Provincial Education Department (No. 17JK0788).

酯键普遍存在于各类精细化学品、医药、农药和功能材料中,酯键的形成在复杂产物合成中往往是最具挑战性的步骤.oxa-Michael加成反应是一类重要的形成碳-氧键的反应,醇作为亲核试剂对αβ-不饱和酮的oxa-Michael加成已被广泛而深入地研究,但使用有机酸为亲核试剂对αβ-不饱和酮的oxa-Michael加成反应由于其内在的挑战性而研究得很少.迄今为止,还没有一例普遍适用的有机酸对αβ-不饱和酮的oxa-Michael加成反应报道.这里,报道了一个碳酸钠水溶液促进的有机酸对αβ-不饱和酮的oxa-Michael加成反应.本反应的底物范围非常广泛,具有很好普适性,反应条件温和,成本低廉,绿色环保,可以用于制备很多类型酯化物,是一类较普遍适用的酯类化合物的合成方法.

关键词: 酯, oxa-Michael加成, 有机酸, α,β-不饱和酮, 碳酸钠水溶液

Ester bonds are found widely in various fine chemicals, medicines, pesticides and functional materials. Despite the apparent simplicity, the construction of ester bonds often constitutes the most challenge in the synthesis of complex molecular containing ester functionality. Oxa-Michael addition represents an important class of organic reactions in carbon-heteroatom bond formation. The use of alcohol donors in oxa-Michael additions is well known. However, the use of carboxylic acid as the donor in the reaction is difficult due to the low activity of acid and a more pronounced reversibility of the reaction. To date, there is no general oxa-Michael addition of acids to α,β-unsaturated ketones reported. Herein, an efficient sodium carbonate promoted oxa-Michael addition of acids to α,β-unsaturated ketones to synthesize esters is reported. With a broad substrate scope, a well-common catalyst and simple operation, the approach provides a facile, practicable, economical, and environmentally benign method for the synthesis of esters.

Key words: esters, oxa-Michael addition, acids, α,β-unsaturated ketones, sodium carbonate aqueous solution