有机化学 ›› 2016, Vol. 36 ›› Issue (8): 1915-1920.DOI: 10.6023/cjoc201601040 上一篇    下一篇

研究简报

5(R)-(l-?氧基)-2(5H)-呋喃酮与溴代丙二酸二乙酯的反应

康海霞a, 白静b, 郗振涛a, 张曼曼a, 傅玉琴a, 邹大鹏b   

  1. a 洛阳师范学院化学化工学院 洛阳 471022;
    b 郑州大学化学与分子工程学院 郑州 450001
  • 收稿日期:2016-01-29 修回日期:2016-03-22 出版日期:2016-08-25 发布日期:2016-05-03
  • 通讯作者: 傅玉琴 E-mail:lyfuyuqin@126.com
  • 基金资助:

    河南省科技发展计划(No. 122300410265)及洛阳师范学院2013年培育基金(No. 2013-PYJJ-006)资助项目.

Reaction of 5(R)-(l-Menthoxy)-2(5H)-furanone with Diethyl Bromomalonate

Kang Haixiaa, Bai Jingb, Xi Zhentaoa, Zhang Manmana, Fu Yuqina, Zou Dapengb   

  1. a College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022;
    b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001
  • Received:2016-01-29 Revised:2016-03-22 Online:2016-08-25 Published:2016-05-03
  • Supported by:

    Project supported by the Foundation of Science and Technology of Henan Province (No.122300410265) and the Fostering Foundation of Luoyang Normal University in 2013 (No. 2013-PYJJ-006).

研究了5(R)-(l-?氧基)-2(5H)-呋喃酮与溴代丙二酸二乙酯在无水K2CO3和相转移催化剂四丁基溴化铵(TBAB)存在下,以乙腈为溶剂,在80 ℃下的反应及产物结构特征. 在上述条件下得到了预期的具有两个乙酯基的手性环丙烷/丁内酯衍生物3,同时还得到了含有一个乙酯基的手性环丙烷/丁内酯化合物5以及少量的含溴产物6. 通过对产物结构分析,提出了产物形成的可能机理.

关键词: 2(5H)-呋喃酮, 环丙烷/丁内酯衍生物, 手性, 合成, 晶体结构

The reaction of 5(R)-(l-menthoxy)-2(5H)-furanone and diethyl bromomalonate was investigated in the presence of anhydrous K2CO3 and phase transfer catalyst tetrabutylammonium bromide (TBAB) using CH3CN as solvent at 80 ℃. In the above condition, the expected novel chiral cyclopropane/butyrolactone derivative 3 with two ethyl ester groups was obtained, and at the same time, another chiral cycloproane/butyrolactone 5 bearing only one ethyl ester group, and trace amount of bromo-substitued compound 6 were also obtained. The possible mechanism was proposed based on the analysis of the products.

Key words: 2(5H)-furanone, cyclopropane/butyrolactone derivative, chiral, synthesis, crystal structure