Aryl (β, β', β''-trifluoro)-tert-butyl : a candidate motif for the discovery of bioactives
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The (β,β′,β″-trifluoro)-tert-butyl (TFTB) group has received very little attention in the literature. This work presents a direct synthesis of this group and explores its properties. The TFTB group arises when the methyl groups of a tert-butyl moiety are exchanged for fluoromethyl groups. Sequential fluoromethylations result in a decrease of Log P (increasing hydrophilicity), ultimately by 1.7 Log P units in the TFTB group relative to that of tert-butyl benzene itself. A focus is placed on synthetic transformations, conformational analysis, and metabolism of the TFTB group in the context of presenting a favorable profile as a motif for the discovery of bioactives.
O'Hagan , D , Cordes , D B , Dobson , L , Oke , O O , Zhang , Q , Cormanich , R , Isanbor , C , McKay , B , Khan , M F , Piscelli , B & Murphy , C 2023 , ' Aryl (β, β', β''-trifluoro)- tert -butyl : a candidate motif for the discovery of bioactives ' , Organic Letters , vol. 25 , no. 37 . https://doi.org/10.1021/acs.orglett.3c02236
Copyright © 2022 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0.
DescriptionFunding: UK Engineering and Physical Sciences Research Council - EP/S030506/1; Commonwealth Scholarship Commission.
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