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

Fumiyuki Kiuchi, Xing Chen, Yoshisuke Tsuda

研究成果: Article査読

15 被引用数 (Scopus)

抄録

Methylation of dibenzoylmethanes with diazomethane always gave Z-β-methoxychalcones, which are the products of kinetically controlled methylation of chelated enol forms of /1-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 fl-methoxychalcone were determined by X-ray crystal structure analysis. All p-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 /Jmethoxyl group and H-8 proton. The spectral data reported for natural ft-methoxychalcones methylpongamol and praecansone A, are attributable to the E-isomers.

本文言語English
ページ(範囲)1862-1871
ページ数10
ジャーナルChemical and Pharmaceutical Bulletin
38
7
DOI
出版ステータスPublished - 1990
外部発表はい

ASJC Scopus subject areas

  • 化学 (全般)
  • 創薬

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