(2R,3S)-2-(3',4'-dihydroxyphenyl)-3,5,9,10-tetrahydroxy-2,3-trans-3,4-dihydro-2H-benzofurano[2,3-h]chromene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2R,3S)-2-(3',4'-dihydroxyphenyl)-3,5,9,10-tetrahydroxy-2,3-trans-3,4-dihydro-2H-benzofurano[2,3-h]chromene
• 英文别名: gambircatechol；(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-[1]benzofuro[2,3-h]chromene-3,5,9,10-tetrol
• 化学式: C₂₁H₁₆O₈
• 分子量: 396.353
• InChiKey: HZIPWFRHYVQIAX-OXJNMPFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  144
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2R,3S)-2-(3',4'-dihydroxyphenyl)-3,5,9,10-tetrahydroxy-2,3-trans-3,4-dihydro-2H-benzofurano[2,3-h]chromene 以 甲醇 、 乙醚 为溶剂， 反应 48.0h， 生成 (2R,3S)-2-(3,4-Dimethoxy-phenyl)-5,9,10-trimethoxy-3,4-dihydro-2H-1,7-dioxa-benzo[c]fluoren-3-ol
  参考文献：
  名称：

  Tyrosinase catalysed biphenyl construction from flavan-3-ol substrates

  摘要：

  Mushroom tyrosinase catalysed oxidation of three flavan-3-ols, viz. catechin, fisetinidol and mesquitol, was conducted to construct biphenyl bonds. Exposure of the flavan-3-ols to tyrosinase and subsequent trapping of the o-quinone intermediates resulted in the formation of novel flavan-3-ol derivatives, the structures of which were elucidated by mono- and two-dimensional 1H-NMR experiments. Application of the methodology resulted in the improved synthesis of the natural flavan-3-ol dimer, mesquitol-[5-->8]-catechin, previously isolated from Prosopis glandulosa.

  DOI：

  10.1016/s0031-9422(99)00476-8
• 作为产物：
  描述：

  (-)-非瑟酮醇 、 儿茶提取物 在 phosphate buffer 、 tyrosinase 作用下， 以 水 为溶剂， 生成 (2R,3S)-2-(3',4'-dihydroxyphenyl)-3,5,9,10-tetrahydroxy-2,3-trans-3,4-dihydro-2H-benzofurano[2,3-h]chromene
  参考文献：
  名称：

  Tyrosinase catalysed biphenyl construction from flavan-3-ol substrates

  摘要：

  Mushroom tyrosinase catalysed oxidation of three flavan-3-ols, viz. catechin, fisetinidol and mesquitol, was conducted to construct biphenyl bonds. Exposure of the flavan-3-ols to tyrosinase and subsequent trapping of the o-quinone intermediates resulted in the formation of novel flavan-3-ol derivatives, the structures of which were elucidated by mono- and two-dimensional 1H-NMR experiments. Application of the methodology resulted in the improved synthesis of the natural flavan-3-ol dimer, mesquitol-[5-->8]-catechin, previously isolated from Prosopis glandulosa.

  DOI：

  10.1016/s0031-9422(99)00476-8

文献信息

• Tyrosinase catalysed biphenyl construction from flavan-3-ol substrates
  作者：Werner Janse van Rensburg、Daneel Ferreira、Elfranco Malan、Jacobus A. Steenkamp

  DOI：10.1016/s0031-9422(99)00476-8

  日期：2000.1

  Mushroom tyrosinase catalysed oxidation of three flavan-3-ols, viz. catechin, fisetinidol and mesquitol, was conducted to construct biphenyl bonds. Exposure of the flavan-3-ols to tyrosinase and subsequent trapping of the o-quinone intermediates resulted in the formation of novel flavan-3-ol derivatives, the structures of which were elucidated by mono- and two-dimensional 1H-NMR experiments. Application of the methodology resulted in the improved synthesis of the natural flavan-3-ol dimer, mesquitol-[5-->8]-catechin, previously isolated from Prosopis glandulosa.