7-亚硝基-N-特戊酰基二氢吲哚的合成——一个微量有机合成教学实验  

Synthesis of 7-Nitroso-N-pivaloyl indoline:A microsynthesis experiment for the undergraduate organic laboratory

作　　者：夏晓峰 朱洁莲 XIA Xiao-feng;ZHU Jie-lian(College of Chemical and Material Engineering,Jiangnan University,Wuxi 214122,China)

机构地区：[1]江南大学化学与材料工程学院,江苏无锡214122

出　　处：《安徽化工》2024年第6期159-162,共4页Anhui Chemical Industry

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)资助。

摘　　要：描述了一个以区域选择性邻位亚硝化反应为知识重点的微量有机合成实验,实验内容契合有机化学实验教学要求。以N-特戊酰基二氢吲哚为原料,NOBF_(4)为亚硝化试剂,AgNO_(3)为Lewis酸催化剂,在室温条件下,实现N-特戊酰基二氢吲哚氮原子邻位的选择性亚硝化反应,并对产物进行红外、核磁表征。该创新实验所用试剂易得,反应条件温和,速率快,产率良好;学生在学习微量有机合成操作的同时,还能够加深理解芳环上亲电取代反应的区域选择性问题以及Lewis酸配位催化的基本原理。Described herein is an organic synthesis experiment focusing on regioselective ortho-nitrosation reaction.The content of this experiment meets the requirements of organic chemistry experiment teaching.Using N-pivaloyl indoline as starting material,NOBF_(4) as nitrosation reagent,AgNO_(3) as Lewis acid catalyst,a selective nitrosation reaction of N-pivaloyl indoline at the ortho position of nitrogen atom was realized at room temperature,and infrared and nuclear magnetic characterization of the product was performed.The reagents used in this experiment are easily available,the reaction condi⁃tions are mild,the rate of reaction is fast,and the yield is good.While students are learning micro-organic synthesis opera⁃tions,they can also deepen their understanding of the regioselectivity of electrophilic substitution reactions on aromatic rings and the basic principle of Lewis acid coordination catalysis.

关 键 词：LEWIS酸催化 区域选择性 亚硝化 微量合成 

分 类 号：G642[文化科学—高等教育学]