Z-E Isomerization of β-Methoxychalcones : Preferred Existence of E-Isomers in Naturally Occurring β-Methoxychalcones

概要

論文の詳細を見る
Methylation of dibenzoylmethanes with diazomethane always gave Z-β-methoxychalcones, which are the products of kinetically controlled methylation of chelated enol forms of β-hydroxychalcones. Z-β-Methoxychalcones were thermodynamically unstable and readily isomerized into more stable E-isomers on contact with silica gel, on keeping in polar solvents, or on exposure to light. The structures of both isomers of the simplest β-methoxychalcone were determined by X-ray crystal structure analysis. All β-methoxychalcones prepared were fully characterized by spectroscopic methods, revealing that the E- and Z-isomers are distinguishable in terms of ultraviolet and ^<13>C-nuclear magnetic resonance spectra, and nuclear Overhauser effect between the β-methoxyl group and H-8 proton. The spectral data reported for natural β-methoxychalcones, methylpongamol and praecansone A, are attributable to the E-isomers.
公益社団法人日本薬学会の論文
1990-07-25