(2R,3S)-2,3-trans-6'-(2'',4'',6''-trihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol

• 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-trans-6'-(2'',4'',6''-trihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol
• 化学式: C₂₁H₁₈O₉
• 分子量: 414.369
• InChiKey: DQZSKAILCSCIEH-GHTZIAJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  171.07
• 氢给体数：
  8.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2R,3S)-2,3-trans-6'-(2'',4'',6''-trihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-3-ol 以 甲醇 、 乙醚 为溶剂， 反应 48.0h， 生成 (2R,3S)-5,7-Dimethoxy-2-(4,5,2',4',6'-pentamethoxy-biphenyl-2-yl)-chroman-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：

  间苯三酚 、 儿茶提取物 在 phosphate buffer 、 tyrosinase 作用下， 以 水 为溶剂， 反应 24.0h， 以46%的产率得到(2R,3S)-2,3-trans-6'-(2'',4'',6''-trihydroxyphenyl)-3',4',5,7-tetrahydroxyflavan-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

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.