Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane

被引：0

作者：

Lu, Yong ^{[1
]}

Chen, Chuo ^{[1
]}

机构：

[1] UT SouthWestern Med Ctr, Dept Biochem, 5323 Harry Hines Blvd, Dallas, TX 75390 USA

来源：

ARKIVOC | 2023年

关键词：

Bicyclo[1.1.1]pentane (BCP); bridgehead amine; steric hindrance; intrinsic nucleophilicity; POTENT; DISRUPTION; INHIBITORS; DISCOVERY;

D O I：

10.24820/ark.5550190.p012.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclo[1.1.1]pentane (BCP) has received substantial interest in the field of synthetic chemistry recently for its potential use as a benzene isostere in medicinal chemistry. Whereas bicyclo[2.2.2]octane (BCO) has also been used as a bioisostere of benzene, the condensation of BCP-amine with nadic anhydride is significantly easier than that of BCO-amine. Analyses of the geometries and the frontier molecular orbitals of these amines suggest that the low steric hindrance and high intrinsic nucleophilicity of BCP-amine together contribute to its exceptional reactivity. [GRAPHICS] .

引用

页数：8

共 32 条

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