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Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups.
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-09-02 , DOI: 10.3762/bjoc.16.182
Benjamin Jeffries 1 , Zhong Wang 1 , Robert I Troup 1 , Anaïs Goupille 2 , Jean-Yves Le Questel 2 , Charlene Fallan 3 , James S Scott 3 , Elisabetta Chiarparin 3 , Jérôme Graton 2 , Bruno Linclau 1
Affiliation  

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.

中文翻译:

异丙基,环丙基和3-氧杂环丁烷基氟化时的亲脂性趋势。

使用直接可比较且易于获得的模型化合物,可以对单个碳原子上的异丙基,环丙基和3-氧杂环丁烷基取代基进行氟化时的亲脂性调节度的系统比较。另外,提供了与相关线性链衍生物的比较,以及在无环前体扩链以产生含环丙基化合物时发生的亲脂性变化。对于所研究的化合物,与环丙基取代基的氟化相比,异丙基取代基的氟化导致更大的亲脂性调节。
更新日期:2020-09-02
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