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

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 a...

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Detalles Bibliográficos
Autores principales: Lu, Yong, Chen, Chuo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10544781/
https://www.ncbi.nlm.nih.gov/pubmed/37786812
http://dx.doi.org/10.24820/ark.5550190.p012.003
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author Lu, Yong
Chen, Chuo
author_facet Lu, Yong
Chen, Chuo
author_sort Lu, Yong
collection PubMed
description 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.
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spelling pubmed-105447812023-10-02 Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane Lu, Yong Chen, Chuo ARKIVOC Article 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. 2023 2023-08-23 /pmc/articles/PMC10544781/ /pubmed/37786812 http://dx.doi.org/10.24820/ark.5550190.p012.003 Text en https://creativecommons.org/licenses/by/4.0/This paper is an open access article distributed under the terms of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) )
spellingShingle Article
Lu, Yong
Chen, Chuo
Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane
title Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane
title_full Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane
title_fullStr Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane
title_full_unstemmed Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane
title_short Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane
title_sort exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10544781/
https://www.ncbi.nlm.nih.gov/pubmed/37786812
http://dx.doi.org/10.24820/ark.5550190.p012.003
work_keys_str_mv AT luyong exceptionalreactivityofthebridgeheadamineonbicyclo111pentane
AT chenchuo exceptionalreactivityofthebridgeheadamineonbicyclo111pentane

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