1,3-偶极环加成反应产物构型的推定

The Configuration Affirmance of 1,3-Dipolar Cycloaddition Product

1,3-偶极环加成反应有多种选择性,因此产物往往也是由多个异构体组成.天然产物青藤碱进行1,3-偶极环加成反应杂环化时,产物理论上有四个异构体,实验中只发现两个异构体.本文分析了青藤碱1,3-偶极环加成反应中的选择性,再根据产物的1 H NMR、13C NMR、NOESY相关谱、电子效应、空间效应的分析,结合理论计算和软件模拟,最终确定了所得两种产物异构体-1和异构体-2的构型.本文的推定方法,在判定具有类似电子效应和空间效应的1,3-偶极环加成反应产物结构时,能起到一定的借鉴作用.

1,3-dipolar cycloaddition displays several selectivities,which will have many isomers in the product.In the progress of heterocyclic modification of sinomenine via 1,3-dipolar cycloaddition,only two isomers were founded out of four theoretical isomers.In this paper,firstly,we illustrated the selectivities of 1,3-dipolar cycloaddition in details,and then confirmed the configuration of the two isomers according to the 1 H NMR,13C NMR,NOESY,electronic and spatial effects,theoretical calculations,simulation of the products.This method,which estimated the configuration of product of 1,3-dipolar cycloaddition reaction,will provide a valuable reference to other work with similar electronic and spatial effects.