Faculty of Pharmaceutical Sciences, Josai International University.
Faculty of Science, Josai University.
Chem Pharm Bull (Tokyo). 2020;68(8):818-821. doi: 10.1248/cpb.c20-00307.
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 F- and H-NMR spectroscopy. Introduction of a substituent at the 4-position in the benzene ring caused a 1.2-2 fold increase in Δδ values when compared with that of FICA. This increase was investigated using a correlation model for 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.
1-氟茚-1-羧酸（FICA）衍生物含有一个单取代的苯环（1b-e），被合成作为它们的甲酯，并通过 F-NMR 和 H-NMR 光谱评估它们作为手性衍生化试剂（CDAs）的潜力。与 FICA 相比，苯环的 4-位引入取代基会导致 Δδ 值增加 1.2-2 倍。使用 F-NMR 的相关模型和（R，S）和（S，S）非对映异构体的 sp 和 ap 构象的稳定性顺序，从 298.15 K 的吉布斯自由能来研究这种增加。
