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使用基于联萘酚的氨基醇作为手性核磁共振溶剂化剂对羧酸进行高效对映体鉴别。

Efficient Enantiodifferentiation of Carboxylic Acids Using BINOL-Based Amino Alcohol as a Chiral NMR Solvating Agent.

作者信息

Li Gaowei, Ma Minshan, Wang Guifang, Wang Xiaojuan, Lei Xinxiang

机构信息

College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, China.

School of Pharmaceutical Sciences, South Central University for Nationalities, Wuhan, China.

出版信息

Front Chem. 2020 May 4;8:336. doi: 10.3389/fchem.2020.00336. eCollection 2020.

DOI:10.3389/fchem.2020.00336
PMID:32432082
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7213237/
Abstract

A new optically active BINOL-amino alcohol has been designed and synthesized in a good yield and applied as chiral nuclear magnetic resonance (NMR) solvating agent for enantioselective recognition. Analysis by H NMR spectroscopy demonstrated that it has excellent enantiodifferentiation properties toward carboxylic acids and non-steroidal anti-inflammatory drugs (14 examples). The non-equivalent chemical shifts (up to 0.641 ppm) of various mandelic acids were evaluated by the reliable peak of well-resolved H NMR signals. In addition, enantiomeric excesses of the ortho-chloro-mandelic acid with different enantiomeric ratio were calculated based on integration of proton well-separated splitting signals.

摘要

一种新型旋光性联萘酚-氨基醇已被设计合成出来,产率良好,并被用作手性核磁共振(NMR)溶剂化剂用于对映选择性识别。通过¹H NMR光谱分析表明,它对羧酸和非甾体抗炎药(14个实例)具有优异的对映体区分性能。通过分辨良好的¹H NMR信号的可靠峰评估了各种扁桃酸的非等效化学位移(高达0.641 ppm)。此外,基于质子分离良好的分裂信号的积分计算了不同对映体比例的邻氯扁桃酸的对映体过量。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f08/7213237/b47b695ce5ba/fchem-08-00336-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f08/7213237/ad83955c48a3/fchem-08-00336-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f08/7213237/59cbf5259f0f/fchem-08-00336-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f08/7213237/b47b695ce5ba/fchem-08-00336-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f08/7213237/ad83955c48a3/fchem-08-00336-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f08/7213237/59cbf5259f0f/fchem-08-00336-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f08/7213237/b47b695ce5ba/fchem-08-00336-g0002.jpg

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