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Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups.

ABSTRACT: 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.

SUBMITTER: Jeffries B

PROVIDER: S-EPMC7476584 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups.

Jeffries Benjamin B Wang Zhong Z Troup Robert I RI Goupille Anaïs A Le Questel Jean-Yves JY Fallan Charlene C Scott James S JS Chiarparin Elisabetta E Graton Jérôme J Linclau Bruno B

Beilstein journal of organic chemistry 20200902

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 subst ...[more]

PMID: 32952731

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