大学化学 >> 2019, Vol. 34 >> Issue (4): 55-60.doi: 10.3866/PKU.DXHX201808002

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手性有机小分子催化剂6, 7-二氢-5H-吡咯并[1, 2-a]咪唑的合成——介绍一个大学有机化学综合实验

谢芳,张振锋,章烨,张万斌*()   

  • 收稿日期:2018-08-02 录用日期:2018-10-16 发布日期:2019-04-28
  • 通讯作者: 张万斌 E-mail:wanbin@sjtu.edu.cn

Synthesis of Chiral Organocatalysts Possessing a Skeleton of 6, 7-Dihydro-5H-pyrrolo[1, 2-a]imidazole: A Comprehensive College Chemistry Experiment

Fang XIE,Zhenfeng ZHANG,Ye ZHANG,Wanbin ZHANG*()   

  • Received:2018-08-02 Accepted:2018-10-16 Published:2019-04-28
  • Contact: Wanbin ZHANG E-mail:wanbin@sjtu.edu.cn

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摘要：

介绍一个由科研成果转化形成的综合有机化学实验——一类手性双环咪唑类亲核有机小分子催化剂的合成及结构表征。该合成实验以咪唑和丙烯醛为原料，在催化量的乙酸存在下，合成手性双环咪唑醇外消旋体。然后利用固定化酶Nov435对该外消旋体进行乙酰化动力学拆分获得光学纯双环咪唑醇酯及醇类化合物。最后通过测定熔点、旋光度、红外（IR）光谱、核磁共振（1H NMR、13C NMR）和高分辨质谱仪（HRMS）对产物结构进行表征，并利用高效液相色谱仪（HPLC）对光学纯双环咪唑醇酯及醇类化合物的光学纯度进行了测定。本实验涵盖了合成、结构表征和光学纯度测定等实验技能训练及动力学拆分及不对称催化酶促反应等专业知识的学习，不仅有益于提高学生的综合实验能力，也可以开拓学生的视野。

关键词: 双环咪唑, 动力学拆分, 有机小分子催化剂

Abstract:

A new and comprehensive chemistry experiment was introduced, which was developed based on our research work. Chiral bicyclic imidazole nucleophilic catalysts were synthesized from the readily available starting materials, imidazole and acrolein, and were separated easily by kinetic resolution using Nov435. The structures were identified by IR, 1H NMR, 13C NMR, HRMS, melting point measurements and optical rotations. This experiment covers training in experimental skills such as synthesis, structural characterization and optical purity measurements. This is not only beneficial to improve the comprehensive experimental ability of the students but also broadens their vision.

Key words: Bicyclic imidazole, Kinetic resolution, Organocatalyst