广西师范大学学报（自然科学版） ›› 2022, Vol. 40 ›› Issue (4): 154-161.doi: 10.16088/j.issn.1001-6600.2021061103

• 研究论文 • 上一篇    下一篇

1,3-二溴丙烷与醇羧酸和胺一锅法生成烯丙基化合物

阴玉栋1,2, 柯善喆1,2, 黄家艳1,2, 邓梦湘1,2, 刘观艳1,2, 程克光1,2*   

  1. 1. 省部共建药用资源化学与药物分子工程国家重点实验室(广西师范大学),广西桂林 541004;
    2. 广西师范大学化学与药学学院,广西桂林 541004
  • 发布日期:2022-08-05
  • 通讯作者: 程克光 (1983—),女,湖北荆州人,广西师范大学教授,博士。E-mail:kgcheng2008@gmail.com
  • 基金资助:
    国家自然科学基金(21562006);广西自然科学基金(2013GXNSFBA019184);2012年度广西教育厅科研项目(201202ZD008);药用资源化学与药物分子工程教育部重点实验室资助课题(CMEMR2012-B03,CMEMR2013-A01);广西师范大学校级重点项目(2010ZD008)

One-pot Generation of Allylated Products from Alcohols, Carboxylic Acids and Amines with 1,3-Dibromopropane by Sodium Hydride

YIN Yudong1,2, KE Shanzhe1,2, HUANG Jiayan1,2, DENG Mengxiang1,2, LIU Guanyan1,2, CHENG Keguang1,2*   

  1. 1. State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University),Guilin Guangxi 541004, China;
    2. School of Chemistry and Pharmacy, Guangxi Normal University, Guilin Guangxi 541004, China
  • Published:2022-08-05

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摘要： 将1,3-二溴丙烷与醇、羧酸和胺反应得到烯丙基化合物。本文运用“一锅法”策略,首先以雌二醇为原料在碱作用下与1,3-二溴丙烷反应,并考察此烯丙基化反应的最佳条件,之后在最佳条件下将其他醇、羧酸和胺替代雌二醇进行反应。实验结果显示,雌二醇与1,3-二溴丙烷在NaH作用下反应得到3,17β-二烯丙氧基雌二醇-1,3,5(10)-三烯而非3-溴丙基衍生物。因此,1,3-二溴丙烷与其他醇、羧酸和胺的“一锅法”反应可在温和条件下以较高产率得到烯丙醚、烯丙酯和烯丙胺。

关键词: 烯丙基醚, 烯丙基化, 1,3-二溴丙烷, 氢化钠, 一锅法

Abstract: 1,3-Dibromopropane was reacted with alcohol, carboxylic acid and amine respectively to obtain a series of allyl compounds. The one-pot approach was used in this study. Firstly, estradiol as a raw material reacted with 1,3-dibromopropane under the action of alkali then the best conditions for this allylation reaction were determined. Under the best conditions, estradiol was replaced with other alcohols, carboxylic acids and amines for the reaction. The experimental results showed that the reaction of estradiol and 1,3-dibromopropane under the action of NaH alkali produced 3,17β-diallyloxyestradiol-1,3,5(10)-triene instead of 3-bromopropyl. The reaction of 1,3-dibromopropane with other alcohols, carboxylic acids and amines got higher yield of allyl ethers, allyl esters and allylamines under relatively mild conditions.

Key words: allyl ether, allylation, 1,3-dibromopropane, sodium hydride, one-pot

中图分类号: 

  • O621.3
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