3-(2-(吡咯烷-1-基)乙基)-3H-吲哚-3-醇 | 1006067-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-(2-(吡咯烷-1-基)乙基)-3H-吲哚-3-醇
• 英文名称: 3-(2-(pyrrolidin-1-yl)ethyl)-3H-indol-3-ol
• CAS: 1006067-43-1
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: BWYHPOOTGNUHOC-UHFFFAOYSA-N

物化性质

• 沸点：
  399.8±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.83
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-(2-(pyrrolidin-1-yl)ethyl)-1H-indole 在 phosphate buffer 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 3-吲哚甲醛 、 4-(2-(1H-吲哚-3-基)乙胺基)丁醛 、 3-(2-(吡咯烷-1-基)乙基)-3H-吲哚-3-醇
  参考文献：
  名称：

  Oxidations of N-(3-Indoleethyl) Cyclic Aliphatic Amines by Horseradish Peroxidase:  The Indole Ring Binds to the Enzyme and Mediates Electron-Transfer Amine Oxidation

  摘要：

  Although oxidations of aromatic amines by horseradish peroxidase (HRP) are well-known, typical aliphatic amines are not substrates of HRP. In this study, the reactions of N-benzyl and N-methyl cyclic amines with HRP were found to be slow, but reactions of N-(3-indoleethyl) cyclic amines were 2-3 orders of magnitude faster. Analyses of pH-rate profiles revealed a dominant contribution to reaction by the amine-free base forms, the only species found to bind to the enzyme. A metabolic study on a family of congeneric N-(3-indoleethyl) cyclic amines indicated competition between amine and indole oxidation pathways. Amine oxidation dominated for the seven- and eight-membered azacycles, where ring size supports the change in hybridization from sp(3) to sp(2) that occurs upon one-electron amine nitrogen oxidation, whereas only indole oxidation was observed for the six-membered ring congener. Optical difference spectroscopic binding data and computational docking simulations suggest that all the arylalkylamine substrates bind to the enzyme through their aromatic termini with similar binding modes and binding affinities. Kinetic saturation was observed for a particularly soluble substrate, consistent with an obligatory role of an enzyme-substrate complexation preceding electron transfer. The significant rate enhancements seen for the indoleethylamine substrates suggest the ability of the bound indole ring to mediate what amounts to medium long-range electron-transfer oxidation of the tertiary amine center by the HRP oxidants. This is the first systematic investigation to document aliphatic amine oxidation by HRP at rates consistent with normal metabolic turnover, and the demonstration that this is facilitated by an auxiliary electron-rich aromatic ring.

  DOI：

  10.1021/ja075905s