大学化学 >> 2026, Vol. 41 >> Issue (10): 309-315.doi: 10.12461/PKU.DXHX202510028

所属专题： 第5届全国大学生化学实验创新设计大赛

化学实验 上一篇    

骨架编辑策略：异喹啉到2-氨基-1-萘甲醛的转化

曾媛媛, 常孝悌, 李静茹, 王琪琳   

  1. 河南大学化学与分子科学学院, 河南 开封 475004
  • 收稿日期:2025-10-10 录用日期:2025-12-26 发布日期:2026-10-13
  • 通讯作者: 王琪琳 E-mail:wangqilin@henu.edu.cn Qilin Wang
  • 基金资助:
    国家自然科学基金(22471059)；河南省研究生教育改革与质量提升工程项目(YJS2026SZKC23)；河南大学2022年度课程思政样板课程

A skeletal editing strategy: Conversion of isoquinoline to 2-amino-1-naphthaldehyde

Yuanyuan Zeng, Xiaoti Chang, Jingru Li, Qilin Wang   

  1. College of Chemistry and Molecular Sciences, Henan University, Kaifeng 475004, Henan Province, China
  • Received:2025-10-10 Accepted:2025-12-26 Published:2026-10-13
  • Contact: Qilin Wang E-mail:wangqilin@henu.edu.cn

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摘要： 与传统官能团转化化学相比，骨架编辑策略可以实现一个复杂分子到另一个复杂分子的快速转化，从而实现结构多样性合成。但是，在本科教学中，无论是理论教学还是实验教学，都还未涉及到骨架编辑相关知识的传授。本实验将骨架编辑策略这一科研前沿领域引入到本科实验教学，通过形式上的“删氮加碳”过程，建立了一种异喹啉到萘甲醛转化的新方法。本实验融合了有机化学实验教学中的多个实验操作，具有反应时间短(1.5 h)、原料廉价易得、操作简单的优点。产物结构经核磁共振波谱、X-射线单晶衍射、高分辨质谱以及熔点进行表征确认。通过本实验，学生不仅了解了骨架编辑的定义、应用价值和合成挑战，还进一步加深了对Diels-Alder反应的理解，巩固了实验室常用的分离操作和分析手段。本实验有利于培养学生分析问题、解决问题的综合能力，有助于激发学生的科研兴趣，培养其创新能力。

关键词: 骨架编辑, Diels-Alder环加成反应, 重排, 实验教学

Abstract: In contrast to conventional functional group transformation chemistry, skeletal editing strategies enable the rapid conversion of one complex molecule into another, thereby facilitating structural diversity in synthesis. However, undergraduate education—whether theoretical or experimental—has yet to incorporate this knowledge. This experiment introduces skeletal editing, a cutting-edge research field, into undergraduate laboratory teaching. Through a formal "nitrogen deletion and carbon insertion" process, a novel method for converting isoquinoline to naphthaldehyde was developed. The experiment integrates multiple operations from organic chemistry laboratory teaching, offering advantages such as short reaction time (1.5 h), cost-effective and readily available starting materials, and straightforward procedures. The product structure was confirmed through NMR spectroscopy, X-ray single-crystal diffraction, high-resolution mass spectrometry, and melting point analysis. This experiment not only enhances students’ understanding of skeletal editing—its definition, applications, and synthetic challenges—but also deepens their comprehension of the Diels-Alder reaction and reinforces fundamental laboratory techniques for separation and analysis. It fosters students’ ability to analyze and solve problems while stimulating their research interest and nurturing innovative thinking.

Key words: Skeletal editing, Diels-Alder cycloaddition, Rearrangement, Experimental teaching