二苄基氨基-1-甲基环己醇和二苄基氨基-1-三氟甲基环己醇异构体的合成。

Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers.

作者信息

Jones D Heulyn, Bresciani Stefano, Tellam James P, Wojno Justyna, Cooper Anthony W J, Kennedy Alan R, Tomkinson Nicholas C O

机构信息

WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.

Molecular Discovery Research, GlaxoSmithKline, Medicines Research Centre, Hertfordshire, SG1 2NY, UK.

出版信息

Org Biomol Chem. 2016 Jan 7;14(1):172-82. doi: 10.1039/c5ob01924a.

DOI:10.1039/c5ob01924a

PMID:26468867

Abstract

The isomers of dibenzylamino-1-methylcyclohexan-1-ol and dibenzylamino-1-trifluoromethylcyclohexan-1-ol have been prepared. The stereochemistry of these compounds was unequivocally assigned through a combination of NMR spectroscopy and single crystal X-ray analysis. The cis-isomer of 3-N,N-dibenzylamino-1-trifluoromethylcyclohexanol and its derivatives display an unusual conformational behaviour in both solution-phase and the solid-state, where the amino group usually adopts an axial conformation.

摘要

已制备出二苄基氨基-1-甲基环己烷-1-醇和二苄基氨基-1-三氟甲基环己烷-1-醇的异构体。通过核磁共振光谱和单晶X射线分析相结合的方法明确确定了这些化合物的立体化学结构。3-N,N-二苄基氨基-1-三氟甲基环己醇的顺式异构体及其衍生物在溶液相和固态中均表现出异常的构象行为，其中氨基通常采取轴向构象。