Synthesis and characterization of stereospecific 1-propargyl-2-(dimethoxymethyl)-1-cyclohexanols

Citation
J. Liu et al., Synthesis and characterization of stereospecific 1-propargyl-2-(dimethoxymethyl)-1-cyclohexanols, ARCH PH RES, 23(2), 2000, pp. 104-111
Citations number
12
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Pharmacology & Toxicology
Journal title
ARCHIVES OF PHARMACAL RESEARCH
ISSN journal
0253-6269 → ACNP
Volume
23
Issue
2
Year of publication
2000
Pages
104 - 111
Database
ISI
SICI code
0253-6269(200004)23:2<104:SACOS1>2.0.ZU;2-H
Abstract
Stereochemical isomers with hydroxy groups were synthesized by reacting 2-( dimethoxymethyl)cyclohexanone with propargylmagnesium bromide. The stereo c hemical structures were identified by NMR spectral interpretation and the g eometry optimization. To assist the NMR interpretation, geometry optimizati on based on semi-empirical AM1 and PM3 methods was applied. Throughout this study, the structures of the two isomers were all determined and H-1 and C -13 NMR spectra were fully assigned. It was proven that the less polar isom er is an axial alcohol and the more polar one is an equatorial alcohol.