6-nitro-2-(2'-hydroxyethyl)indole

• 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: 6-nitro-2-(2'-hydroxyethyl)indole
• 英文别名: 2-(6-nitro-1H-indol-2-yl)ethanol
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: JHTSRMJHKGWOFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-4-硝基苯酚 在 四(三苯基膦)钯 吡啶 、 copper(l) iodide 、 四丁基碘化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 6-nitro-2-(2'-hydroxyethyl)indole
  参考文献：
  名称：

  Stepwise and one-pot cross-coupling–heteroannulation approaches toward 2-substituted C5-, C6-, and C7-nitroindoles

  摘要：

  A general and efficient synthesis of 2-substituted C5-, C6-, and C7-nitroindoles has been established. Starting from commercially available 2-amino nitrophenols, C5-, C6-, and C7-nitroindoles were synthesized via the stepwise Pd-catalyzed cross-coupling of nitro 2-trifloxyanilides with 1-alkynes followed by the t-BuOK-mediated heteroannulation. A Pd-catalyzed one-pot coupling-heteroannulation procedure was carried out by using nitro 2-trifluoroacetamidoaryl triflates. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.034

文献信息

• Stepwise and one-pot cross-coupling–heteroannulation approaches toward 2-substituted C5-, C6-, and C7-nitroindoles
  作者：Li-Ping Sun、Xiang-Hong Huang、Wei-Min Dai

  DOI：10.1016/j.tet.2004.09.034

  日期：2004.11

  A general and efficient synthesis of 2-substituted C5-, C6-, and C7-nitroindoles has been established. Starting from commercially available 2-amino nitrophenols, C5-, C6-, and C7-nitroindoles were synthesized via the stepwise Pd-catalyzed cross-coupling of nitro 2-trifloxyanilides with 1-alkynes followed by the t-BuOK-mediated heteroannulation. A Pd-catalyzed one-pot coupling-heteroannulation procedure was carried out by using nitro 2-trifluoroacetamidoaryl triflates. (C) 2004 Elsevier Ltd. All rights reserved.