大学化学 >> 2023, Vol. 38 >> Issue (10): 250-257.doi: 10.3866/PKU.DXHX202212063

化学实验 上一篇    下一篇

钯催化串联环化反应合成2-苄基-3, 4-二羰基-6-苯基-9-乙烯基-2-氮杂螺[4.4]壬烷-7, 7-二羧酸乙酯——介绍一个有机化学综合实验

罗一诚1, 高延峰1, 林维晟2, 苗志伟1,*()   

  1. 1 南开大学化学学院, 元素有机化学国家重点实验室, 天津 300071
    2 武夷学院生态与资源工程学院, 福建 武夷山 354300
  • 收稿日期:2022-12-23 录用日期:2023-03-07 发布日期:2023-03-22
  • 通讯作者: 苗志伟 E-mail:miaozhiwei@nankai.edu.cn
  • 基金资助:
    国家自然科学基金项目(22071113);国家大学生创新创业训练计划(20222010452);福建省南平市科技计划项目(N2020Z008)

Synthesis of Diethyl 2-Benzyl-3, 4-dioxo-6-phenyl-9-vinyl-2-azaspiro [4.4]nonane-7, 7-dicarboxylate through Palladium Catalyzed Tandem Cyclization: Introducing a Comprehensive Experiment of Organic Chemistry

Yicheng Luo1, Yanfeng Gao1, Weisheng Lin2, Zhiwei Miao1,*()   

  1. 1 State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
    2 Department of Ecological and Resources Engineering, Wuyi University, Wuyishan 354300, Fujian Province, China
  • Received:2022-12-23 Accepted:2023-03-07 Published:2023-03-22
  • Contact: Zhiwei Miao E-mail:miaozhiwei@nankai.edu.cn

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摘要：

开展有机化学综合实验有利于锻炼学生的实验技能，培养学生的创新能力，激发学生的独立思考能力和研究意识。本文介绍了一个有机化学综合实验，以2-乙烯基环丙烷-1, 1-二甲酸二乙酯和1-苄基-4-亚苄基-2, 3-吡咯烷酮为反应物，利用钯催化串联环化反应合成2-苄基-3, 4-二羰基-6-苯基-9-乙烯基-2-氮杂螺[4.4]壬烷-7, 7-二羧酸乙酯，并利用核磁共振氢谱(1H NMR)、碳谱(13C NMR)和高分辨质谱(HRMS)对产物结构进行表征。

关键词: 有机化学综合实验, 钯催化, 串联环化反应, 2-苄基-3, 4-二羰基-6-苯基-9-乙烯基-2-氮杂螺[4.4]壬烷-7, 7-二羧酸乙酯, 合成与结构表征

Abstract:

The comprehensive experiment of organic chemistry is conducive to training students' experimental skills, cultivating their innovative ability, and stimulating their independent thinking ability and research consciousness. This article presents a comprehensive organic chemistry experiment in which 2-vinylcyclopropane-1, 1-diethyl diformate and 1-benzyl-4-benzylidene-2, 3-pyrrolidone were used as reactants to synthesize 2-benzyl-3, 4-dicarbonyl-6-phenyl-9-vinyl-2-azanone-7, 7-dicarboxylate ethyl ester by palladium-catalyzed tandem cyclization reaction. 1H NMR, 13C NMR and HRMS characterized the structure of the product.

Key words: Organic chemistry comprehensive experiment, Palladium catalysis, Tandem cyclization reaction, Diethyl 2-benzyl-3, 4-dioxo-6-phenyl-9-vinyl-2-azaspiro[4.4]nonane-7, 7-dicarboxylate, Synthesis and structural characterization