253663-98-8Relevant academic research and scientific papers
A simple synthesis of (±)-α-cuparenone
Chavan, Subhash P.,Patil, Sachindra S.,Ravindranathan
, p. 13417 - 13422 (1999)
A short and simple synthesis of (±)-α-cuparenone from 4-methyl- acetophenone via acid catalyzed decomposition of a β,γ-unsaturated-α- diazoketone is described.
Tandem Blaise/retro-Blaise reaction for the nitrile-mediated regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky Reagents) to 1-alkynes and 1,3-enynes
Kim, Ju Hyun,Chun, Yu Sung,Lee, Sang-Gi
, p. 11483 - 11493 (2013/12/04)
We report the novel use of a nitrile as a mediator to achieve the regioselective intermolecular addition of unstabilized zinc ester enolates (Reformatsky reagents) to 1-alkynes and 1,3-enynes. This reaction is made possible by a reversible addition of enolates to a nitrile (Blaise reaction), generating a zinc aza-enolate that, unlike zinc ester enolates, can add intermolecularly to 1-alkynes and 1,3-enynes. Subsequent removal of the nitrile through a retro-Blaise reaction generates the targeted addition product. This method is combined with a Diels-Alder reaction and subsequent oxidative aromatization, providing a tandem one-pot de novo construction of α-arylated alkanoates from Reformatsky reagents.
SYNTHESIS, MOLECULAR PROPERTIES AND PHARMACOLOGICAL ACTIVITY OF SOME p-SUBSTITUTED (E)- AND (Z)-α,β-DIMETHYLCINNAMIC ACIDS
Balsamo, Aldo,Crotti, Paolo,Macchia, Bruno,Macchia, Franco,Martinelli, Adriano,et al.
, p. 327 - 332 (2007/10/02)
A series of p-substituted (E)- and (Z)-α,β-dimethylcinnamic acids has been prepared and pharmacologically tested.The configurations of the acids prepared were determined from their NMR spectra.The UV spectra and the acid dissociation constants are reported.The collected data show that an extensive conjugation between the aryl and carboxy groups via the double bond does not exist, due to the steric hindrance of the α,β-dimethyl substitution on the cinnamic system.
