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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 provi...
| Autores principales: | , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2020
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7476584/ https://www.ncbi.nlm.nih.gov/pubmed/32952731 http://dx.doi.org/10.3762/bjoc.16.182 |
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| author | Jeffries, Benjamin Wang, Zhong Troup, Robert I Goupille, Anaïs Le Questel, Jean-Yves Fallan, Charlene Scott, James S Chiarparin, Elisabetta Graton, Jérôme Linclau, Bruno |
| author_facet | Jeffries, Benjamin Wang, Zhong Troup, Robert I Goupille, Anaïs Le Questel, Jean-Yves Fallan, Charlene Scott, James S Chiarparin, Elisabetta Graton, Jérôme Linclau, Bruno |
| author_sort | Jeffries, Benjamin |
| collection | PubMed |
| description | 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. |
| format | Online Article Text |
| id | pubmed-7476584 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2020 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-74765842020-09-18 Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups Jeffries, Benjamin Wang, Zhong Troup, Robert I Goupille, Anaïs Le Questel, Jean-Yves Fallan, Charlene Scott, James S Chiarparin, Elisabetta Graton, Jérôme Linclau, Bruno Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2020-09-02 /pmc/articles/PMC7476584/ /pubmed/32952731 http://dx.doi.org/10.3762/bjoc.16.182 Text en Copyright © 2020, Jeffries et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
| spellingShingle | Full Research Paper Jeffries, Benjamin Wang, Zhong Troup, Robert I Goupille, Anaïs Le Questel, Jean-Yves Fallan, Charlene Scott, James S Chiarparin, Elisabetta Graton, Jérôme Linclau, Bruno Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups |
| title | Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups |
| title_full | Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups |
| title_fullStr | Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups |
| title_full_unstemmed | Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups |
| title_short | Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups |
| title_sort | lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7476584/ https://www.ncbi.nlm.nih.gov/pubmed/32952731 http://dx.doi.org/10.3762/bjoc.16.182 |
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