2-(4-羟基苯基)苯并吡喃-7-酮 | 78776-51-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-(4-羟基苯基)苯并吡喃-7-酮
• 英文名称: 2-<4-Hydroxy-phenyl>-chromen-7-on
• 英文别名: 2-(4-Hydroxyphenyl)-7H-1-benzopyran-7-one；2-(4-hydroxyphenyl)chromen-7-one
• CAS: 78776-51-9
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: DQKOJTJVZKIZLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-hydroxy-2-(4'-hydroxyphenyl)benzopyrilium chloride 以 水 为溶剂， 生成 2-(4-羟基苯基)苯并吡喃-7-酮 、 1-苯基-3-(2,4,4-三羟基-1,5-环己二烯-1-基)-2-丙烯-1-酮
  参考文献：
  名称：

  Pina, Fernando; Benedito, Lina; Melo, Maria Joao, Anales de Quimica, 1997, vol. 93, # 2, p. 111 - 118

  摘要：

  DOI：

文献信息

• Photochromism of the Synthetic 4',7-Dihydroxyflavylium Chloride
  作者：Paulo Figueiredo、Joao C. Lima、Helena Santos、Marie Claude Wigand、Raymond Brouillard、Antonio L. Macanita、Fernando Pina

  DOI：10.1021/ja00083a011

  日期：1994.2

  The synthetic compound 4',7-dihydroxyflavylium chloride shows an interesting photochromic effect at moderately acidic pH values. Pale yellow solutions of this compound, equilibrated in the dark at pH 3.4, become bright yellow upon irradiation with 313-nm light. Switching off the light, gives back the initial pale yellow solution. Photochemical methods, H-1 NMR, and molecular orbital calculations were used to elucidate this photochromic behavior. In solutions equilibrated in the dark (pH < 5.7), the existence of two main species in equilibrium is demonstrated: the colored flavylium cation and the colorless trans-chalcone. Freshly prepared solutions of this compound at pH 6.2 reveal the existence of another colored form, the quinonoidal base, which reacts thermally to yield trans-chalcone. An analogous reaction takes place in freshly prepared solutions at pH 3.4: the flavylium cation is partially converted into trans-chalcone. The extent of such conversion is pH dependent and nearly complete at pH 6.2. Irradiation of trans-chalcone at the wavelength of 313 nm partially gives back the initial colored form, with concomitant formation of small amounts of photodegradation products. The turnover of the photochromic reaction is greater at pH 3.4 than at pH 6.2. The photochromism is explained on the basis of a trans-cis photoisomerization. In fact the relative stability of the two chalcone isomers is reversed in the excited state, as predicted from molecular orbital calculations.