吲哚自由基 | 50614-06-7

• 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
• 中文名称: 吲哚自由基
• 英文名称: indole radical
• 英文别名: indolyl
• CAS: 50614-06-7
• 化学式: C₈H₆N
• 分子量: 116.142
• InChiKey: DAIGRYNHHZOIRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  吲哚自由基 在 oxonium 作用下， 以 水 为溶剂， 生成 吲哚
  参考文献：
  名称：

  吲哚的单电子氧化和吲哚基的酸碱性质

  摘要：

  DOI：

  10.1021/j100300a039
• 作为产物：
  描述：

  吲哚 以 水 为溶剂， 生成 吲哚自由基
  参考文献：
  名称：

  吲哚的单电子氧化和吲哚基的酸碱性质

  摘要：

  DOI：

  10.1021/j100300a039

文献信息

• Photochemical reactions of triplet acetone with indole, purine, and pyrimidine derivatives
  作者：Kunihiko Kasama、Akiko Takematsu、Shigeyoshi Arai

  DOI：10.1021/j100210a035

  日期：1982.6
• Acid properties of short-lived radicals and their appearance in photoinduced hydrogen atom transfer
  作者：K. B. Petrushenko、A. I. Vokin、V. K. Turchaninov、S. E. Korostova

  DOI：10.1007/bf00962652

  日期：1988.1
• Photoreaction between 2-Benzoylthiophene and Phenol or Indole
  作者：Julia Pérez-Prieto、Francisco Boscá、Raquel E. Galian、Agustín Lahoz、Luis R. Domingo、Miguel A. Miranda

  DOI：10.1021/jo034225e

  日期：2003.6.1

  Laser flash photolysis, density functional theory (DFT) calculations, and product studies have been performed to understand the mechanism of photoreduction of 2-benzoylthiophene (BT) in the presence of phenol or indole. Time-resolved experiments showed that BT ketyl (BTH) and phenoxy (PhO) or indolyl (In) radicals are generated with high rate constants and quantum yields close to 1. However, low conversions (specially in the case of indole) of the starting reagents are obtained upon prolonged lamp irradiation, indicating that recombination within the radical pairs must occur to a large extent, regenerating the starting materials. The solvent-dependence of the quenching rate constants, together with DFT theoretical studies, indicate fundamental differences between the mechanisms of the reaction of BT triplet with phenol and indole. Thus, data for phenol agree with the involvement of a hydrogen-bonded exciplex BT HOPh, where concerted electron and proton transfer leads to the (BTHOPh)-O-... radical pair. However, in the case of indole, electron transfer at the (BTHIn)-H-... stage precedes proton transfer. Finally, C-C cross-coupling products have been isolated and characterized in the preparative irradiation of BT in the presence of phenol and indole. The structures of the products have been confirmed by alternative synthesis.
• One-electron oxidation of indoles and acid-base properties of the indolyl radicals
  作者：Xinhua. Shen、Johan. Lind、Gabor. Merenyi

  DOI：10.1021/j100300a039

  日期：1987.7