3,3-Dimethyl-1,2-dihydroindole-5,6-diol | 374756-91-9

• 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: 3,3-Dimethyl-1,2-dihydroindole-5,6-diol
• CAS: 374756-91-9
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: URDKVTXSNKYRPN-UHFFFAOYSA-N

物化性质

• 沸点：
  352.9±42.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3,3-Dimethyl-1,2-dihydroindole-5,6-diol 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Catalytic Turnover of Benzylamine by a Model for the Lysine Tyrosylquinone (LTQ) Cofactor of Lysyl Oxidase

  摘要：

  Lysyl oxidase differs from other copper an-tine oxidases in that its active quinone cofactor reflects cross-linking of a lysyl residue into the tyrosine-derived quinone nucleus found in the plasma and other copper amine oxidases. A model for the lysyl oxidase cofactor (LTQ), 3,3-dimethyl-2,3-dihydroindole-5,6-quinone (4), was synthesized and found to be stable to both hydrolysis and oxidation events that prevent simpler models from functioning as turnover catalysts. We show that 4 catalyzes the aerobic oxidative deamination of benzylamine, though turnover eventually ceases on account of oxidation of the dihydrobenzoxazole tautomer of the "product Schiff base" to form a benzoxazole, a reaction that may be physiologically relevant. The mechanism of the overall reaction profile was elucidated by a combination of optical and NMR spectroscopy and O-2 uptake studies.

  DOI：

  10.1021/ja011141j
• 作为产物：
  描述：

  3,3-dimethyl-2,3-dihydroindole-5,6-quinone 在 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 生成 3,3-Dimethyl-1,2-dihydroindole-5,6-diol
  参考文献：
  名称：

  Catalytic Turnover of Benzylamine by a Model for the Lysine Tyrosylquinone (LTQ) Cofactor of Lysyl Oxidase

  摘要：

  Lysyl oxidase differs from other copper an-tine oxidases in that its active quinone cofactor reflects cross-linking of a lysyl residue into the tyrosine-derived quinone nucleus found in the plasma and other copper amine oxidases. A model for the lysyl oxidase cofactor (LTQ), 3,3-dimethyl-2,3-dihydroindole-5,6-quinone (4), was synthesized and found to be stable to both hydrolysis and oxidation events that prevent simpler models from functioning as turnover catalysts. We show that 4 catalyzes the aerobic oxidative deamination of benzylamine, though turnover eventually ceases on account of oxidation of the dihydrobenzoxazole tautomer of the "product Schiff base" to form a benzoxazole, a reaction that may be physiologically relevant. The mechanism of the overall reaction profile was elucidated by a combination of optical and NMR spectroscopy and O-2 uptake studies.

  DOI：

  10.1021/ja011141j