19F NMR spectroscopy as a tool to detect rotations in fluorine substituted phenyl compounds

被引：8

作者：

Sun, Mingming ^{[1
,2
,3
]}

Chen, Wuhong ^{[3
]}

Zhang, Tao ^{[3
]}

Liu, Zhenjun ^{[3
]}

Wei, Junchao ^{[1
,4
]}

Xi, Ning ^{[2
,3
]}

机构：

[1] Nanchang Univ, Coll Chem, 999 Xuefu Ave, Nanchang 330031, Jiangxi, Peoples R China

[2] Ningbo Univ, Sch Med, 818 Fenghua Rd, Ningbo 315211, Zhejiang, Peoples R China

[3] Sunshine Lake Pharmaceut Co Ltd, Dongyangguang Hitech Pk, Dongguan 523871, Guangdong, Peoples R China

[4] Nanchang Univ, Sch Stomatol, 49 Fuzhou Rd, Nanchang 330006, Jiangxi, Peoples R China

来源：

TETRAHEDRON | 2020年 / 76卷 / 48期

基金：

中国国家自然科学基金;

关键词：

Atropisomerism; Rotamer; F-19; NMR; N-Phenyl gamma-lactam; Pyrazolone; DISCOVERY; INHIBITOR; CHIRALITY;

D O I：

10.1016/j.tet.2020.131679

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Atropisomerism becomes a popular structural feature in modern drug discovery. Using N-phenyl gamma-lactam and phenyl-pyrazolone scaffolds, we showed that distinct F-19 NMR peaks were present in atropisomers and dual signals emerged for covalently identical fluorine nuclei in hindered rotamers. Factors affecting F-19 NMR chemical shifts in these molecules were discussed. We demonstrated that F-19 NMR spectroscopy can be used to differentiate and detect atropisomers and rotamers in conformationally restricted molecules. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：13

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