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dc.contributor.authorO'Hagan, David
dc.contributor.authorCordes, David Bradford
dc.contributor.authorDobson, Luca
dc.contributor.authorOke, Oluwayinka Omobolanle
dc.contributor.authorZhang, Qingzhi
dc.contributor.authorCormanich, Rodrigo
dc.contributor.authorIsanbor, Chukwuemeka
dc.contributor.authorMcKay, Benjamin
dc.contributor.authorKhan, Mohd Faheem
dc.contributor.authorPiscelli, Bruno
dc.contributor.authorMurphy, Cormac
dc.date.accessioned2023-09-13T16:30:06Z
dc.date.available2023-09-13T16:30:06Z
dc.date.issued2023-09-22
dc.identifier.citationO'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.3c02236en
dc.identifier.issn1523-7060
dc.identifier.otherPURE: 293709430
dc.identifier.otherPURE UUID: 58809b37-37ca-4b01-b5e3-bfff7f4a0910
dc.identifier.otherORCID: /0000-0002-0510-5552/work/142499022
dc.identifier.otherORCID: /0000-0002-5366-9168/work/142499309
dc.identifier.otherScopus: 85172034347
dc.identifier.urihttps://hdl.handle.net/10023/28367
dc.descriptionFunding: UK Engineering and Physical Sciences Research Council - EP/S030506/1; Commonwealth Scholarship Commission.en
dc.description.abstractThe (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.
dc.format.extent6802
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.rightsCopyright © 2022 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0.en
dc.subjectDASen
dc.titleAryl (β, β', β''-trifluoro)-tert-butyl : a candidate motif for the discovery of bioactivesen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. Institute of Behavioural and Neural Sciencesen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doihttps://doi.org/10.1021/acs.orglett.3c02236
dc.description.statusPeer revieweden
dc.identifier.grantnumberEP/S030506/1en


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