背景(考古学)
双环分子
高分子科学
戒指(化学)
生物结合
共价键
纳米技术
化学
组合化学
材料科学
立体化学
生物
有机化学
古生物学
作者
Carmel Kelly,John A. Milligan,Leon J. Tilley,Taylor Sodano
出处
期刊:Chemical Science
[The Royal Society of Chemistry]
日期:2022-01-01
卷期号:13 (40): 11721-11737
被引量:43
摘要
The unique chemistry of small, strained carbocyclic systems has long captivated organic chemists from a theoretical and fundamental standpoint. A resurgence of interest in strained carbocyclic species has been prompted by their potential as bioisosteres, high fraction of sp3 carbons, and limited appearance in the patent literature. Among strained ring systems, bicyclo[1.1.0]butane (BCB) stands apart as the smallest bicyclic carbocycle and is amongst the most strained carbocycles known. Despite the fact that BCBs have been synthesized and studied for well over 50 years, they have long been regarded as laboratory curiosities. However, new approaches for preparing, functionalizing, and using BCBs in "strain-release" transformations have positioned BCBs to be powerful synthetic workhorses. Further, the olefinic character of the bridgehead bond enables BCBs to be elaborated into various other ring systems and function as covalent warheads for bioconjugation. This review will discuss the recent developments in the synthesis and functionalization of BCBs as well as the applications of these strained rings in synthesis and drug discovery. An overview of the properties and the historical context of this interesting structure will be provided.
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