17556-19-3Relevant articles and documents
A concise method for the synthesis of 2-tetralone by titanium tetrachloride-promoted cyclization of 4-aryl-2-hydroxybutanal diethyl acetal
Hon, Yung-Son,Devulapally, Rammohan
scheme or table, p. 5713 - 5715 (2009/12/09)
4-Aryl-2-hydroxybutanal diethyl acetal, prepared from the reaction of benzyl Grignard reagent and glycidaldehyde diethyl acetal, was treated with titanium tetrachloride to give 2-tetralone in good yield. This highly efficient transformation involves tande
Heteroaryl β-tetralin ureas as novel antagonists of human TRPV1
Jetter, Michele C.,Youngman, Mark A.,McNally, James J.,McDonnell, Mark E.,Zhang, Sui-Po,Dubin, Adrienne E.,Nasser, Nadia,Codd, Ellen E.,Flores, Christopher M.,Dax, Scott L.
, p. 6160 - 6163 (2008/03/18)
We report on a series of α-substituted-β-tetralin-derived and related phenethyl-based isoquinolinyl and hydroxynaphthyl ureas as potent antagonists of the human TRPV1 receptor. The synthesis and Structure-activity relationships (SAR) of the series are described.
Electronic effects on enol acidity and keto-enol equilibrium constants for ring-substituted 2-tetralones
Yao,Pollack
, p. 634 - 638 (2007/10/03)
Equilibrium constants for the ionization of a variety of phenyl-substituted 2-tetralones (pK(a)(K)), for the ionization of their enols (pK(a)(E)), and for keto-enol tautomerization (PK(E)) were determined. Hammett plots of pK(a)(K) and pK(a)(E) vs. σ are linear with slopes (-ρ) of -1.66 ± 0.06 and -0.90 ± 0.03, respectively, except for deviations of the points corresponding to 6-nitro-2-tetralone (1b) and its enol. We have previously attributed the negative deviation of 1b from the correlation for the acidities of the ketones obtained with the more limited set of data to the lack of a free electron pair on C-1 of the free tetralone (Nevy et al.). The negative deviation of the point for 1b from the correlation for the acidities of the enols suggests that charge transfer from the hydroxyl group of the enol to the nitro group is less important than it is for phenols. This study represents the first systematic study of electronic effects on equilibria among ketone, enol, and enolate in aqueous solution.