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Synthesis and Evaluation of FICA Derivatives as Chiral Derivatizing Agents.
Chemical & Pharmaceutical Bulletin ( IF 1.5 ) Pub Date : 2020-08-01 , DOI: 10.1248/cpb.c20-00307
Tomoyo Kamei 1 , Tamiko Takahashi 1 , Hiroyuki Teramae 2 , Jyunichi Koyanagi 1
Affiliation  

1-Fluoroindan-1-carboxyic acid (FICA) derivatives containing a monosubstituted benzene ring (1be) were synthesized as their methyl esters and their potential as chiral derivatizing agents (CDAs) were assessed by both 19F- and 1H-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 19F-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.

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中文翻译:

作为手性衍生剂的FICA衍生物的合成与评价。

合成了含有一个单取代苯环(1be)的1-氟丹丹-1-羧酸(FICA)衍生物作为它们的甲酯,并通过19 F-和1 H-NMR评估了它们作为手性衍生剂(CDA)的潜力光谱学。在苯环的4位上的取代基的引入导致了一个Δδ1.2-2倍增加˚F当与FICA的比较的值。使用19 F-NMR的相关性模型和(R的上平面sp)和反上平面ap)构象异构体的稳定性顺序研究了这种增加S)和(SS)非对映体的吉布斯自由能在298.15 K。

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更新日期:2020-08-23
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