文章基本信息

标题：Synthesis and Evaluation of FICA Derivatives as Chiral Derivatizing Agents
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作者：Tomoyo Kamei ; Tamiko Takahashi ; Hiroyuki Teramae 等
期刊名称：Chemical and Pharmaceutical Bulletin
印刷版ISSN：0009-2363
电子版ISSN：1347-5223
出版年度：2020
卷号：68
期号：8
页码：818-821
DOI：10.1248/cpb.c20-00307
出版社：The Pharmaceutical Society of Japan
摘要：1-Fluoroindan-1-carboxyic acid (FICA) derivatives containing a monosubstituted benzene ring ( 1b – e ) were synthesized as their methyl esters and their potential as chiral derivatizing agents (CDAs) were assessed by both 19 F- and 1 H-NMR spectroscopy. Introduction of a substituent at the 4-position in the benzene ring caused a 1.2–2 fold increase in ΔδF values when compared with that of FICA. This increase was investigated using a correlation model for 19 F-NMR and by the order of the stability of the synperiplanar ( sp ) and antiperiplanar ( ap ) conformers of the ( R , S ) and ( S , S ) diastereomers from the Gibbs’ free energy at 298.15 K.
关键词：chiral derivatizing agent;4-bromo-1-fluoroindan-1-carboxylic acid;19F-NMR;correlation model;Gibbs’ free energy