ISSN:
0749-1581
Keywords:
Ring-methylated reversed esters of pethidine
;
Opioid ligands
;
1H NMR
;
13C NMR
;
Stereochemistry
;
Conformational analysis N-Protonated epimers
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The NMR spectra (chiefly 1H) of isomeric 2,5- and 2,3-dimethyl-4-phenyl-4-piperidinols, related esters and trans- 2,6-dimethyl-4-propionyloxy-4-phenylpiperidine HCl (all N-methylated) have been assigned and analysed in terms of solute conformation. Preferred forms include 4-ax-phenyl and 4-eq-phenyl chairs and, in the case of the γ-2,3-dimethyl-4-piperidinol base, a boat conformation. In several cases the existence of pairs of N-protonated epimers has been demonstrated. The findings are important both to the conformational analysis of saturated six-membered heterocycles and to stereoactivity analyses of opioid ligands of the 4-arylpiperidine class.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260301011
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