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

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
1860-5397
2141-2150
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
5051f89a-b801-4746-8f20-457fdcbed396
Graton, Jérôme
12432694-552e-4a40-9935-9ff7c77fbf07
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Jefferies, Benjamin
09ae24cd-c590-4843-a548-c3b7bfe148bb
Wang, Zhong
fe914552-33f1-4f0a-b8a1-52b82e8cb89e
Troup, Robert Ian
4e5eae00-ac0a-44a4-8c32-1042d6261c46
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.
0fff1208-5c96-4490-8898-b9cc0692c8f3
Chiarparin, Elisabetta
5051f89a-b801-4746-8f20-457fdcbed396
Graton, Jérôme
12432694-552e-4a40-9935-9ff7c77fbf07
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, 2020 (16), 2141-2150. (doi:10.3762/bjoc.16.182).

Record type: Article

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.

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Accepted/In Press date: 20 August 2020
e-pub ahead of print date: 2 September 2020
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
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 14 Sep 2020 16:30
Last modified: 18 Feb 2021 16:55

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