Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups
Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups
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.
aliphatic fluorination, cyclopropane, isopropyl, isostere, lipophilicity, oxetane
2141-2150
Jefferies, Benjamin
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Wang, Zhong
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Troup, Robert Ian
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Goupille, Anaïs
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Le Questel, Jean-Yves
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Fallan, Charlene
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Scott, James S.
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Chiarparin, Elisabetta
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Graton, Jérôme
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Linclau, Bruno
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2 September 2020
Jefferies, Benjamin
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Wang, Zhong
fe914552-33f1-4f0a-b8a1-52b82e8cb89e
Troup, Robert Ian
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Goupille, Anaïs
b2817234-3328-44c4-8dc7-88c43174c332
Le Questel, Jean-Yves
38aea4ae-64a3-43b7-8049-ea2f351459f2
Fallan, Charlene
2753821a-35b7-4cbf-851d-9a3a8929af2b
Scott, James S.
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Chiarparin, Elisabetta
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Graton, Jérôme
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Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Jefferies, Benjamin, Wang, Zhong, Troup, Robert Ian, Goupille, Anaïs, Le Questel, Jean-Yves, Fallan, Charlene, Scott, James S., Chiarparin, Elisabetta, Graton, Jérôme and Linclau, Bruno
(2020)
Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups.
Beilstein Journal of Organic Chemistry, 16 (16), .
(doi:10.3762/bjoc.16.182).
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.
Text
1860-5397-16-182
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More information
Accepted/In Press date: 20 August 2020
e-pub ahead of print date: 2 September 2020
Published date: 2 September 2020
Additional Information:
Copyright © 2020, Jeffries et al.; licensee Beilstein-Institut.
Keywords:
aliphatic fluorination, cyclopropane, isopropyl, isostere, lipophilicity, oxetane
Identifiers
Local EPrints ID: 443805
URI: http://eprints.soton.ac.uk/id/eprint/443805
ISSN: 1860-5397
PURE UUID: 016dc6ed-c4ec-4ec4-a523-ccfdd4f011b9
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Date deposited: 14 Sep 2020 16:30
Last modified: 17 Mar 2024 02:51
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Contributors
Author:
Benjamin Jefferies
Author:
Robert Ian Troup
Author:
Anaïs Goupille
Author:
Jean-Yves Le Questel
Author:
Charlene Fallan
Author:
James S. Scott
Author:
Elisabetta Chiarparin
Author:
Jérôme Graton
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