N-benzyl-N-hydroxy-1-(3'-indolyl)propylamine | 200347-71-3

• 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: N-benzyl-N-hydroxy-1-(3'-indolyl)propylamine
• 英文别名: N-benzyl-N-[1-(1H-indol-3-yl)propyl]hydroxylamine
• CAS: 200347-71-3
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: ZJWZXAJXFGREHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基吲哚 、 N-benzyl-N-hydroxy-1-(3'-indolyl)propylamine 在 三甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以74%的产率得到1-(3'-indolyl)-1-(2"-methyl-3"-indolyl)propane
  参考文献：
  名称：

  The Reactions of Nitrones with Indoles

  摘要：

  The reaction of nitrones with various indole derivatives has been studied. When the reaction was promoted by ClSiMe3, the isolated products were 3,3'-diindolylalkanes. With HCl as the activating reagent, 3-indolylhydroxylamines were isolated. The diastereoselectivity of this condensation with a nitrone derived from cysteine was investigated. A method for the introduction of an alkylhydroxylamino group onto position 2 of indole, the synthesis of three natural 3,3'-diindolylalkanes and of non-symmetric diindolylalkanes are also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01051-0
• 作为产物：
  描述：

  吲哚 、 (Z)-N-propylidene(phenyl)methanamine oxide 在 甲醇 、 乙酰氯 作用下， 反应 2.0h， 以94%的产率得到N-benzyl-N-hydroxy-1-(3'-indolyl)propylamine
  参考文献：
  名称：

  The Reactions of Nitrones with Indoles

  摘要：

  The reaction of nitrones with various indole derivatives has been studied. When the reaction was promoted by ClSiMe3, the isolated products were 3,3'-diindolylalkanes. With HCl as the activating reagent, 3-indolylhydroxylamines were isolated. The diastereoselectivity of this condensation with a nitrone derived from cysteine was investigated. A method for the introduction of an alkylhydroxylamino group onto position 2 of indole, the synthesis of three natural 3,3'-diindolylalkanes and of non-symmetric diindolylalkanes are also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01051-0

文献信息

• The reaction of nitrones with indoles. Synthesis of asymmetrical diindolylalcanes
  作者：Jean-Noël Denis、Hélène Mauger、Yannick Vallée

  DOI：10.1016/s0040-4039(97)10302-1

  日期：1997.12

  The reaction of nitrones with indoles in the presence of HCl gives indolyl N-hydroxylamines. In the presence of Me3SiCl symmetrical diindolylalcanes are obtained. A synthesis of asymmetrical diindolylalcanes and the syntheses of three natural symmetrical diindolylalcanes are reported. (C) 1997 Published by Elsevier Science Ltd.