1H-indol-3-ylmethyl radical

• 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: 1H-indol-3-ylmethyl radical
• 英文别名: indol-3-ylmethyl radical；3-indolylmethyl radical
• 化学式: C₉H₈N
• 分子量: 130.169
• InChiKey: AVCOFCNUGPPYGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  过氧化苯甲酰 、 3-(1H-indol-3-ylmethyl)-1-methyl-2-phenylindole 生成 1H-indol-3-ylmethyl radical
  参考文献：
  名称：

  COLONNA, M., ATTI ACCAD. SCI. IST. BOLOGNA CL. SCI. FIS. REND., 1979-1980, 7, N 1, 155+

  摘要：

  DOI：

文献信息

• Free-Radical Intermediates and Stable Products in the Oxidation of Indole-3-acetic acid
  作者：Luis P. Candeias、Lisa K. Folkes、Madeleine F. Dennis、Kantilal B. Patel、Steven A. Everett、Michael R. L. Stratford、Peter Wardman

  DOI：10.1021/j100091a031

  日期：1994.10

  The free-radical intermediates and the stable products formed on one-electron oxidation of indole-3-acetic acid (IAA) in aqueous solution were investigated. The dibromine radical anion generated radiolytically reacted with IAA to yield the IAA radical cation. In acid solution, the latter decays by a first-order process (k = 1.8 x 10(4) s(-1)) to yield carbon dioxide and the skatole radical. At pH 7 it deprotonates (pK(a) = 5.09 +/- 0.02), giving the indolyl radical, which decays only by a bimolecular process (rate constant of first-order reactions <100 s(-1)) which yields indole-3-carbinol as one of the products. Under steady-state irradiation at pH 7 the free radicals had a sufficient lifetime to allow the small fraction of radical cation present in equilibrium to undergo decarboxylation, consistent with the observed formation of carbon dioxide. Glutathione reacted with the indolyl radical, regenerating IAA, and with the skatole radical to yield skatole. In the presence of oxygen the skatole radical is rapidly converted to a peroxyl radical, which appears to decay only by bimolecular reactions with indole-3-aldehyde as one of the products. No evidence was found for the reaction of the peroxyl radical with glutathione or for elimination of superoxide.