5,5',5'',5''',6,6',6'',6'''-octahydroxy-2,4':2',3'':2'',4'''-tetraindolyl | 1061759-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5,5',5'',5''',6,6',6'',6'''-octahydroxy-2,4':2',3'':2'',4'''-tetraindolyl
• 英文别名: 2-(5,6-dihydroxy-1H-indol-4-yl)-3-[4-(5,6-dihydroxy-1H-indol-2-yl)-5,6-dihydroxy-1H-indol-2-yl]-1H-indole-5,6-diol
• CAS: 1061759-18-9
• 化学式: C₃₂H₂₂N₄O₈
• 分子量: 590.549
• InChiKey: BMOCEIJGUHRXJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  44
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  225
• 氢给体数：
  12
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,5',5'',5''',6,6',6'',6'''-octahydroxy-2,4':2',3'':2'',4'''-tetraindolyl 、 乙酸酐 在 吡啶 作用下， 生成 5,5',5'',5''',6,6',6'',6'''-octaacetoxy-2,4':2',3'':2'',4'''-tetraindolyl
  参考文献：
  名称：

  The First 5,6-Dihydroxyindole Tetramer by Oxidation of 5,5‘,6,6‘-Tetrahydroxy- 2,4‘-biindolyl and an Unexpected Issue of Positional Reactivity en Route to Eumelanin-Related Polymers

  摘要：

  The first tetramer of the eumelanin precursor 5,6-dihydroxyindole has been obtained, as the acetyl derivative, by peroxidase/H2O2-induced oxidative coupling of 5,5',6,6'-tetrahydroxy-2,4'-biindolyl (2) in the presence of Zn2+ ions. The tetramer, 5,5',5' ',5' '',6,6',6' ',6' ''-octaacetoxy-2,4':2',3' ':2' ',4' ''-tetraindolyl (acetylated 7), incorporates an unprecedented 2,3'-biindolyl substructure suggestive of a different positional reactivity of the 5,6-dihydroxyindole system when framed into a dimeric scaffold.

  DOI：

  10.1021/ol070268w
• 作为产物：
  描述：

  5,5',6,6'-tetrahydroxy-2,4'-biindolyl 在 zinc(II) sulfate HEPPSO buffer 、 双氧水 、 peroxidase 、 sodium dithionite 作用下， 以 甲醇 、 水 为溶剂， 反应 0.01h， 生成 5,5',5'',5''',6,6',6'',6'''-octahydroxy-2,4':2',3'':2'',4'''-tetraindolyl
  参考文献：
  名称：

  The First 5,6-Dihydroxyindole Tetramer by Oxidation of 5,5‘,6,6‘-Tetrahydroxy- 2,4‘-biindolyl and an Unexpected Issue of Positional Reactivity en Route to Eumelanin-Related Polymers

  摘要：

  The first tetramer of the eumelanin precursor 5,6-dihydroxyindole has been obtained, as the acetyl derivative, by peroxidase/H2O2-induced oxidative coupling of 5,5',6,6'-tetrahydroxy-2,4'-biindolyl (2) in the presence of Zn2+ ions. The tetramer, 5,5',5' ',5' '',6,6',6' ',6' ''-octaacetoxy-2,4':2',3' ':2' ',4' ''-tetraindolyl (acetylated 7), incorporates an unprecedented 2,3'-biindolyl substructure suggestive of a different positional reactivity of the 5,6-dihydroxyindole system when framed into a dimeric scaffold.

  DOI：

  10.1021/ol070268w

文献信息

• The First 5,6-Dihydroxyindole Tetramer by Oxidation of 5,5‘,6,6‘-Tetrahydroxy- 2,4‘-biindolyl and an Unexpected Issue of Positional Reactivity en Route to Eumelanin-Related Polymers
  作者：Lucia Panzella、Alessandro Pezzella、Alessandra Napolitano、Marco d'Ischia

  DOI：10.1021/ol070268w

  日期：2007.3.1

  The first tetramer of the eumelanin precursor 5,6-dihydroxyindole has been obtained, as the acetyl derivative, by peroxidase/H2O2-induced oxidative coupling of 5,5',6,6'-tetrahydroxy-2,4'-biindolyl (2) in the presence of Zn2+ ions. The tetramer, 5,5',5' ',5' '',6,6',6' ',6' ''-octaacetoxy-2,4':2',3' ':2' ',4' ''-tetraindolyl (acetylated 7), incorporates an unprecedented 2,3'-biindolyl substructure suggestive of a different positional reactivity of the 5,6-dihydroxyindole system when framed into a dimeric scaffold.