大学化学 >> 2022, Vol. 37 >> Issue (12): 2111036.doi: 10.3866/PKU.DXHX202111036

化学实验 上一篇    下一篇

(2R,3R)-1,4-二甲氧基-1,1,4,4-四苯基-2,3-丁二醇的合成——推荐一个大学有机化学综合实验

胡晓允(), 马玲, 尹欣然, 陈丹, 周忠强, 张道洪   

  • 收稿日期:2021-11-10 录用日期:2022-02-10 发布日期:2022-03-17
  • 通讯作者: 胡晓允 E-mail:xyhu@mail.scuec.edu.cn
  • 作者简介:胡晓允, Email: xyhu@mail.scuec.edu.cn
  • 基金资助:
    湖北省一流本科课程建设项目《有机化学》(YLKCS20012);湖北省优秀基层教学组织(JCZZS2002);中南民族大学重点教研项目(JYZD22014)

Synthesis and Characterization of (2R,3R)-1,4-Dimethoxyl-1,1,4,4-tetraphenyl-2,3-butanediol : A Recommended Comprehensive Chemistry Experiment

Xiaoyun Hu(), Ling Ma, Xinran Yin, Dan Chen, Zhongqiang Zhou, Daohong Zhang   

  • Received:2021-11-10 Accepted:2022-02-10 Published:2022-03-17
  • Contact: Xiaoyun Hu E-mail:xyhu@mail.scuec.edu.cn

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摘要：

“(2R,3R)-1,4-二甲氧基-1,1,4,4-四苯基-2,3-丁二醇的合成与表征”是“化学综合实验”课程的一个创新实验。(2R,3R)-1,4-二甲氧基-1, 1,4,4-四苯基-2,3-丁二醇是一种应用广泛的手性二醇，但其合成方案制备成本较高、合成操作繁琐且具有一定的危险性，不适合作为本科教学实验开设。该综合实验以天然酒石酸酯为手性源，与苯基格氏试剂反应制得(2R,3R)-1,1,4,4-四苯基丁四醇；基于其高度区域选择性2,3-环亚硫酸酯化反应，利用甲醇与卤代烃的亲核取代反应引入甲氧基，避开MeI/NaH的羟基醚化方案，制得(2R,3R)-1,4-二甲氧基-1,1,4,4-四苯基-2,3-丁二醇，降低了制备成本，简化了实验操作步骤。该实验涵盖了格氏反应、亲核取代、水解反应等经典反应类型，涉及无水操作、萃取、重结晶及薄层色谱检测等合成操作和熔点、比旋光度测定、核磁共振等表征手段。该综合实验和基础有机化学实验紧密衔接，培养和提高了学生的综合实验能力，加深了学生对有机化学理论知识的理解，让学生深刻认识到高度区域选择性反应的设计在有机合成中的重要性，激发了学生的科研兴趣和创新意识，适合作为大学综合化学实验开设。

关键词: 综合实验, 区域选择性反应, (2R,3R)-1,4-二甲氧基-1,1,4,4-四苯基-2,3-丁二醇, 绿色化学

Abstract:

Synthesis and characterization of (2R,3R)-1,4-dimethoxyl-1,1,4,4-tetraphenyl-2,3-butanediol is an innovative experiment from the "comprehensive chemistry experiment" course. While (2R,3R)-1,1,4,4-tetraphenylbutanetetraol has found diverse applications in asymmetric organic synthesis, its preparation cost is high, and the synthesis operation is cumbersome and dangerous. (2R,3R)-1,4-dimethoxyl-1,1,4,4-tetraphenyl-2,3-butanediol was synthesized via a highly regioselective reaction of (2R,3R)-1,1,4,4-tetraphenyl-butanetetraol. We propose a comprehensive chemistry experiment that includes classical reaction types, synthetic operations, and characterization analysis. This experiment will strengthen students' understanding of the theoretical knowledge of organic chemistry and cultivate and improve students' comprehensive experimental ability. In addition, this experiment also can establish the green chemistry concept among students and stimulate students' scientific research interest and their awareness of scientific research innovations. Therefore, this experiment is suitable for use as a college chemistry experiment.

Key words: Comprehensive experiment, Region-selective reaction, (2R,3R)-1,4-Dimethoxyl-1,1,4,4-tetraphenyl-2,3-butanediol, Green chemistry