Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups.
aliphatic fluorination
cyclopropane
isopropyl
isostere
lipophilicity
oxetane
Journal
Beilstein journal of organic chemistry
ISSN: 1860-5397
Titre abrégé: Beilstein J Org Chem
Pays: Germany
ID NLM: 101250746
Informations de publication
Date de publication:
2020
2020
Historique:
received:
19
07
2020
accepted:
20
08
2020
entrez:
21
9
2020
pubmed:
22
9
2020
medline:
22
9
2020
Statut:
epublish
Résumé
A systematic comparison of lipophilicity modulations upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl substituents, at a single carbon atom, is provided using directly comparable, and easily accessible model compounds. In addition, comparison with relevant linear chain derivatives is provided, as well as lipophilicity changes occurring upon chain extension of acyclic precursors to give cyclopropyl containing compounds. For the compounds investigated, fluorination of the isopropyl substituent led to larger lipophilicity modulation compared to fluorination of the cyclopropyl substituent.
Identifiants
pubmed: 32952731
doi: 10.3762/bjoc.16.182
pmc: PMC7476584
doi:
Types de publication
Journal Article
Langues
eng
Pagination
2141-2150Informations de copyright
Copyright © 2020, Jeffries et al.; licensee Beilstein-Institut.
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