大学化学 >> 2017, Vol. 32 >> Issue (6): 82-85.doi: 10.3866/PKU.DXHX201611017

化学实验 上一篇    下一篇

4'-{2-[5-(4-羧基苯基)呋喃基]}-2, 2':6', 2″-三联吡啶的合成——推荐一个大学有机化学实验

付伟伟*(),易庆,金霞,旷香,汤子晴   

  • 发布日期:2017-06-03
  • 通讯作者: 付伟伟 E-mail:w.w.fu@hynu.edu.cn
  • 基金资助:
    湖南省重点学科基金资助项目;功能金属有机材料湖南省普通高校重点实验室开放基金资助项目(GN14K02);湖南省教育厅科学研究项目(16B037);材料物理与化学湖南省十二五重点建设学科项目和功能金属有机化合物湖南省高校科技创新团队项目

Synthesis of 4'-[5-(4-Carboxylphenylfuran)-2-yl)]-2, 2':6', 2"-Terpyridine: A Proposed Organic Chemistry Experiment

Wei-Wei FU*(),Qing YI,Xia JIN,Xiang KUANG,Zi-Qing TANG   

  • Published:2017-06-03
  • Contact: Wei-Wei FU E-mail:w.w.fu@hynu.edu.cn
  • Supported by:
    湖南省重点学科基金资助项目;功能金属有机材料湖南省普通高校重点实验室开放基金资助项目(GN14K02);湖南省教育厅科学研究项目(16B037);材料物理与化学湖南省十二五重点建设学科项目和功能金属有机化合物湖南省高校科技创新团队项目

摘要:

介绍一个面向大学高年级本科生的综合性有机化学实验——4'-{2-[5-(4-羧基苯基)呋喃基]}-2, 2':6', 2″-三联吡啶的合成与结构表征。以糠醛、对氨基苯甲酸为原料经低温条件下的偶联反应制备5-(4-羧基苯基)呋喃-2-甲醛,并以其和2-乙酰基吡啶为原料,在碱性条件下以氨水为氮源合成目标产物。通过熔点测定、红外光谱和核磁共振氢谱对其结构进行表征。该实验合成路线成熟,包括芳环偶联、α, β-不饱和酮的合成、Michael加成等内容,能达到多方面对学生进行锻炼之目的,是一个值得推荐的有机化学实验。

关键词: 三联吡啶, 红外光谱, 核磁共振氢谱, 偶联反应, Michael加成

Abstract:

The synthesis and characterization of 4'-[5-(4-carboxylphenylfuran)-2-yl)]-2, 2':6', 2″-terpyridine is an exploratory experiment completed by senior undergraduates. 4-(5-formylfuran-2-yl) benzoic acid was obtained with furfural and 4-aminobenzoic acid as raw materials by a coupled reaction at low temperature. The target compound was obtained with 4-(5-formylfuran-2-yl) benzoic acid and 2-acetylpyridine in the presence of ammonium hydroxide and characterized by melting point, IR and 1H NMR measurements. It is proposed as an organic chemistry experiment as it contains coupling reaction of aromatic rings, synthesis of α, β-unsaturated ketone, Michael addition reaction which would be beneficial for training of students.

Key words: Terpyridine, Infrared spectrum, 1H NMR spectroscopy, Coupling reaction, Michael addition

MSC2000: 

  • G64