可见光催化合成异喹啉酮生物碱的创新实验及课程转化实践思考

引用本文: 唐雨榕, 时允仁, 徐溢, 秦波, 徐彦芹, 蔡云飞. 可见光催化合成异喹啉酮生物碱的创新实验及课程转化实践思考[J]. 大学化学, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087 shu

Citation: Yurong Tang, Yunren Shi, Yi Xu, Bo Qin, Yanqin Xu, Yunfei Cai. Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone[J]. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087 shu

可见光催化合成异喹啉酮生物碱的创新实验及课程转化实践思考

重庆大学化学化工学院, 重庆 400044
基金项目:
重庆市教学改革重点项目(232010)；重庆大学本科实验教学改革项目(2021S37)

摘要: 为有效拓展现阶段本科有机化学教学实验开设的范围，让学生了解学科前沿研究热点与新合成技术，本实验以异喹啉酮生物碱的光化学合成为导向，将有机光化学和连续流动化学融合运用于本科实验教学。本实验选择氮化碳半导体材料作为非均相光催化剂，氧气作为绿色、经济的氧化剂，在可见光介导下实现异喹啉酮生物碱的合成。实验主要由间歇光反应和连续流光反应合成异喹啉酮生物碱以及合成高附加值天然产物corydaldine三部分组成，涉及搭建简易连续流光化学反应装置、反应监测、分离纯化、产物表征等多个重要环节，指导学生认识光化学反应知识，也让学生熟悉微量有机反应中薄层分析法、柱层析及相关仪器的操作，并将所学的红外、核磁共振波谱法等理论知识运用到产物的结构分析中，提升学生的主观能动性、综合实践能力和环保意识。本创新实验竞赛项目符合实验绿色化、微型化的新理念，适合于在化学化工专业本科生的有机化学实验和综合化学实验中开展，将其转化本科实验教学项目，可充分体现“以赛促建”“以赛促教”“以赛促学”的重要意义。

关键词:

English

Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone

School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China
Received Date: 29 November 2023
Revised Date: 04 February 2024

Abstract: This experiment introduces undergraduate students to the forefront of organic chemistry and new synthetic methodologies through the synthesis of isoquinolinone guided by photochemistry. By integrating organic photochemistry and continuous flow chemistry, the experiment aims to broaden the scope of undergraduate organic chemistry laboratory teaching. Carbon nitride (g-C₃N₄) is employed as a heterogeneous photocatalyst, while oxygen serves as a safe and atom-economic oxidant, enabling the synthesis of isoquinolinone under visible-light irradiation in a continuous flow setup. The experiment encompasses both batch and continuous flow photochemical synthesis of isoquinolinone, as well as the preparation of the natural product corydaldine. Students are involved in various aspects of the experiment, including the installation of a simple flow photochemical reactor, reaction monitoring, product purification, and characterization. Through this project, students not only gain insights into photochemical reactions but also cultivate their creativity and research skills in the realm of green and sustainable chemistry. They acquire hands-on experience in thin-layer chromatography, column chromatography, and spectroscopic analysis techniques like IR and NMR, enhancing their practical skills and environmental awareness. This innovative experiment aligns with the principles of green chemistry and miniaturization and is suitable for incorporation into undergraduate laboratory courses such as Organic Chemistry Laboratory and Comprehensive Chemistry Laboratory. Its introduction into laboratory teaching can enrich teaching practices, promote active learning, and elevate the quality of practical education.

Key words:

1. [1]
  Schultz, D. M.; Yoon, T. P. Science 2014, 343, 985.Schultz, D. M.; Yoon, T. P. Science 2014, 343, 985.
2. [2]
  王燕, 张绮彤, 张彬, 王宇. 大学化学, 2022, 37 (9), 2203098.
3. [3]
  Zheng, Y.; Lin, L.; Wang, B.; Wang, X. Angew. Chem. Int. Ed. 2015, 54(44), 12868.Zheng, Y.; Lin, L.; Wang, B.; Wang, X. Angew. Chem. Int. Ed. 2015, 54(44), 12868.
4. [4]
  马科星, 杨俊杰, 陈柏丞, 沈永雯, 胡秀琴, 许鹏飞. 大学化学, 2023, 38 (4), 106.
5. [5]
  Cai, Y.; Tang, Y.; Fan, L. L.; Lefebvre, Q.; Hou, H.; Rueping, M. ACS Catal. 2018, 8(10), 9471.Cai, Y.; Tang, Y.; Fan, L. L.; Lefebvre, Q.; Hou, H.; Rueping, M. ACS Catal. 2018, 8(10), 9471.
6. [6]
  Geng, P. X.; Tang, Y. R.; Pan, G. L.; Wang, W. T.; Hu, J. C.; Cai, Y. F. Green Chem. 2019, 21, 6116.Geng, P. X.; Tang, Y. R.; Pan, G. L.; Wang, W. T.; Hu, J. C.; Cai, Y. F. Green Chem. 2019, 21, 6116.
7. [7]
  Kaila, N.; Follows, B.; Leung, L,; Thomason, J.; Huang, A.; Moretto, A.; Janz, K.; Lowe, M.; Mansour, T.; Hubeau, C.; et al. J. Med. Chem. 2014, 57(4), 1299.Kaila, N.; Follows, B.; Leung, L,; Thomason, J.; Huang, A.; Moretto, A.; Janz, K.; Lowe, M.; Mansour, T.; Hubeau, C.; et al. J. Med. Chem. 2014, 57(4), 1299.
8. [8]
  Sterckx, H.; Morel, B.; Maes, B. U. W. Angew. Chem. Int. Ed. 2019, 58(24), 7946.Sterckx, H.; Morel, B.; Maes, B. U. W. Angew. Chem. Int. Ed. 2019, 58(24), 7946.
9. [9]
  郭举, 高艺, 胡诗敏, 樊可, 龙思会. 大学化学, 2022, 37 (6), 2201038.

扫一扫看文章

计量

PDF下载量: 4
文章访问数: 252
HTML全文浏览量: 22

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

可见光催化合成异喹啉酮生物碱的创新实验及课程转化实践思考

English

Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

可见光催化合成异喹啉酮生物碱的创新实验及课程转化实践思考

English

Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs