摘要
针对本科实验教学中缺乏安全有效的亲电氟代反应的相关内容,设计了含氟精细化学品中间体的合成与表征综合性化学实验。实验利用N-羟基邻苯二甲酰亚胺(NHPI)作为催化剂,1-氯甲基-4-氟-1,4-二氮杂双环[2.2.2]辛烷二(四氟硼酸)盐(Selectfluor)为亲电氟化试剂,在温和条件下实现了四氢喹啉芳环上的高选择性亲电氟代反应,并对合成产物进行了红外、核磁和高分辨质谱表征。实验从有机合成、分离纯化、结构表征等多方面对学生进行理论和实验技能的综合训练,具备综合性、设计性和应用性,贴合精细化工专业学科发展。通过实验教学使学生掌握了含氟精细化学品的制备方法,拓展了学生的专业视野,培养了科研创新理念以及独立思考、分析解决问题的能力。
To address the gap in undergraduate experimental teaching regarding safe and effective electrophilic fluorination,we have developed a comprehensive chemical experiment focused on the synthesis and characterization of fluorine-containing fine chemical intermediates.The experiment utilizes N-hydroxyphthalimide(NHPI)as a catalyst and 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate)salt(Selectfluor)as an electrophilic fluorination reagent.This approach enables highly selective electrophilic fluorination of the tetrahydroquinoline aromatic ring under mild conditions,with the product characterized by infrared spectroscopy(IR),nuclear magnetic resonance(NMR),and high-resolution mass spectrometry(HRMS).The experiment provides a comprehensive training platform for students,enhancing their theoretical understanding and experimental skills in organic synthesis,separation and purification,and structural characterization.It embodies the elements of comprehensiveness,innovation,and practical application,aligning with the development goals of the fine chemical engineering curriculum.Through this experimental module,students gain hands-on experience in the preparation of fluorine-containing fine chemicals,broaden their professional perspectives,and develop critical thinking,problem-solving skills,and a mindset oriented towards scientific research and innovation.
作者
夏晓峰
朱洁莲
Xiaofeng Xia;Jielian Zhu(College of Chemical and Material Engineering,Jiangnan University,Wuxi 214122,Jiangsu Province,China)
出处
《大学化学》
CAS
2024年第10期344-352,共9页
University Chemistry
基金
江南大学研究生教育教学改革研究与实践课题(YJSJGYB22_005)
江南大学2022年度实验室管理专项课题(JDSYS202206)。
关键词
综合实验
亲电氟代反应
含氟精细化学品中间体
半微量合成
Comprehensive experiment
Electrophilic fluorination reaction
Fluorine-containing fine chemical intermediate
Semi-micro synthesis
