Base-catalyzed C-2 exchange and epimerization of cocaine analogs: methyl 3.beta.-substituted 8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylates

Autor:	J. F. Casale, F. I. Carroll, Anita H. Lewin, J. P. Bowen
Rok vydání:	1992
Předmět:	chemistry.chemical_compound Deprotonation Reaction rate constant Molecular model Deuterium Bicyclic molecule Chemistry Organic Chemistry Epimer Medicinal chemistry Catalysis Octane
Zdroj:	The Journal of Organic Chemistry. 57:4906-4912
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00044a028
Popis:	The kinetic and thermodgnamic parameters associated with epimeric 2-carbomethoxy-3β-substituted tropanes have been investigated by means of base-catalyzed deuterium incorporation, epimerization, and by molecular modeling. The equilibration results, as well as the molecular mechanics calculations, showed the 2α-epimers to be more stable than the 2β-epimers. However, it was found that the energies of the transitions states for deprotonation at C-2 from the β-face were higher than those for deprotonation from the α-face
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::5b640dbdfcd0a414cf42753e04ed6e35 https://doi.org/10.1021/jo00044a028 Zobrazit plný text záznamu