大学化学 >> 2022, Vol. 37 >> Issue (5): 2111018.doi: 10.3866/PKU.DXHX202111018

所属专题: 第2届全国大学生化学实验创新设计竞赛

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一锅三步由硝基芳烃合成邻氨基酚衍生物

孙承博, 张珠宝, 陈艺中, 匡禹豪, 廖小建(), 冯鹏举()   

  • 收稿日期:2021-11-08 录用日期:2021-11-10 发布日期:2022-03-30
  • 通讯作者: 廖小建,冯鹏举 E-mail:tliaoxj@jnu.edu.cn;pfeng@jnu.edu.cn
  • 作者简介:Email: tliaoxj@jnu.edu.cn (廖小建)
    Email: pfeng@jnu.edu.cn (冯鹏举)
    第一联系人:

    共同第一作者,对本文工作同等贡献

  • 基金资助:
    广东省珠江人才计划青年拔尖人才(2017GC010302);基于学生综合素质和创新能力提升的实验实践教学体系改革(H20200510);中国高等教育学会2020年度“实验室管理研究”专项课题

One-Pot, Three-Step Synthesis of o-Aminophenol Derivatives from Nitro Arenes

Chengbo Sun, Zhubao Zhang, Yizhong Chen, Yuhao Kuang, Xiaojian Liao(), Pengju Feng()   

  • Received:2021-11-08 Accepted:2021-11-10 Published:2022-03-30
  • Contact: Xiaojian Liao,Pengju Feng E-mail:tliaoxj@jnu.edu.cn;pfeng@jnu.edu.cn

摘要:

硝基的选择性还原,羟胺的选择性保护,以及[3, 3]-σ重排都是有机化学的基础内容。本实验将此三个基本反应融入于3.5 h的紧凑一锅法化学反应中,反应现象丰富且便于观察,利用薄层色谱能方便监测反应的进程。反应可以从简单的硝基芳烃一锅获取高官能化邻氨基酚衍生物,同时三步反应可以分解为三个单独的反应,且均能高收率得到相应化合物。产物可由硅胶柱层析纯化,化合物结构通过质谱、核磁共振波谱的解析进一步确定。该反应立足有机化学硝基官能团基础知识,适用于本科生学习官能团转化知识,观测多种实验现象,同时反应操作多样,用时紧凑,产率高,在邻氨基酚类衍生物制备中具有广泛的应用潜力。

关键词: 一锅法, 选择性还原, 羟胺选择性保护, [3, 3]-σ重排, 邻氨基酚

Abstract:

The selective reduction of nitro groups, selective protection of hydroxylamine, and the [3, 3]-σ rearrangement are fundamental reactions in organic chemistry. This experiment systematically incorporates three basic reactions into a compact, one-pot chemical transformation in 3.5 h. The reaction occurs abundantly, and can be easily monitored by thin-layer chromatography. High value-added functionalized o-aminophenol derivatives could be obtained from simple nitro arenes in one pot. In addition, the three-step reaction can be run separately with high yields. The final product can be purified using silica gel column chromatography, and the structure can be determined via high-resolution mass spectrometry and nuclear magnetic resonance spectroscopy. This reaction is based on fundamental organic chemistry concepts. It is important for undergraduates to learn functional group transformations and develop the ability to observe various experimental phenomena. Moreover, the reaction has high efficiency in a short time and may have a wide range of applications in the preparation of functional o-aminophenol derivatives.

Key words: One-pot procedure, Selective reduction, Protection of hydroxylamine, [3, 3]-σ Rearrangement, o-Aminophenol

MSC2000: 

  • G64