182122-29-8Relevant academic research and scientific papers
Facilitated intramolecular conjugate addition of amides of 3-(3′,6′-dioxo-2′,4′-dimethyl-1′,4′- cyclohexadienyl)-3,3-dimethylpropionic acid. 2. Kinetics of degradation
Nicolaou, Michalis G.,Wolfe, Janet L.,Schowen, Richard L.,Borchardt, Ronald T.
, p. 6633 - 6638 (2007/10/03)
The chemical stability studies of amides of 3-(3′,6′-dioxo-2′,4′-dimethyl-1′,4′- cyclohexadienyl)-3,3-dimethylpropionic acid (Qa) [Qop(a-j)] were conducted in order to determine the utility of this redox-sensitive system as a potential prodrug promoiety o
Facilitated Intramolecular Conjugate Addition of N-(p-Methoxyphenyl)-3-(3',6'-dioxo-2',4'-dimethylcyclohexa-1',4'-dienyl)-3,3-dimethylpropionamide. 1. Product Characterization
Wolfe, Janet L.,Velde, David Vander,Borchardt, Ronald T.
, p. 6138 - 6142 (2007/10/02)
N-(p-Methoxyphenyl)-3-(3',6'-dioxo-2',4'-dimethylcyclohexa-1',4'-dienyl)-3,3-dimethylpropionamide (1), a pro-prodrug model, was chosen to study the reaction of quinone propionic amides in mildly acidic aqueous solution.The quinone propionic amide 1 equilibrates rapidly with its hydroxy dienone 6 and undergoes a much slower 1,4 conjugate addition to form its enol spirolactam 4.The enol spirolactam 4 then tautomerizes to give the keto spirolactam 5.Spectroscopic evidence suggests that the keto spirolactam 5 is present as a diastereomeric mixture, wherein the preferred diastereomer has the 2'-methyl and the lactam nitrogen anti to each other.
