4-bromo-N-(2,2-diethoxyethyl)aniline | 75934-32-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-bromo-N-(2,2-diethoxyethyl)aniline
• CAS: 75934-32-6
• 化学式: C₁₂H₁₈BrNO₂
• 分子量: 288.184
• InChiKey: ZLKOVQFZZKRIPG-UHFFFAOYSA-N

物化性质

• 沸点：
  368.5±42.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 4-bromo-N-(2,2-diethoxyethyl)aniline 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 1-苄基-5-溴-1H-吲哚
  参考文献：
  名称：

  General and efficient synthesis of 2,3-unsubstituted indoles catalyzed by acidic mesoporous molecular sieves

  摘要：

  A general and efficient method for the synthesis of 2,3-unsubstituted indoles has been established by the intramolecular cyclization of N-benzyl 2-anilinoacetals. Acidic mesoporous molecular sieve (MCM-41-SO3H) has shown excellent catalytic activity on this transformation, and the 2,3-unsubstituted indoles bearing 7-substituent or strong electron-withdrawing substituents also could be achieved by this protocol. Moreover, the heterogeneous catalyst, MCM-41-SO3H, could be conveniently recovered and reused without obvious loss of the catalytic activity. This work will provide an economic and environmental-benign method for the construction of various indole derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.026
• 作为产物：
  描述：

  2-溴-1,1-二乙氧基乙烷 、 4-溴苯胺 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以54%的产率得到4-bromo-N-(2,2-diethoxyethyl)aniline
  参考文献：
  名称：

  Synthesis of indoles from N-(trifluoroacetyl)-2-anilino acetals

  摘要：

  DOI：

  10.1021/jo00317a026

文献信息

• Synthesis of indoles from N-(trifluoroacetyl)-2-anilino acetals
  作者：J. Eric Nordlander、David B. Catalane、Kirtivan D. Kotian、Randall M. Stevens、Jerome E. Haky

  DOI：10.1021/jo00317a026

  日期：1981.2
• General and efficient synthesis of 2,3-unsubstituted indoles catalyzed by acidic mesoporous molecular sieves
  作者：Nan Sun、Lingfen Hong、Fang Huang、Hong Ren、Weimin Mo、Baoxiang Hu、Zhenlu Shen、Xinquan Hu

  DOI：10.1016/j.tet.2013.03.026

  日期：2013.5

  A general and efficient method for the synthesis of 2,3-unsubstituted indoles has been established by the intramolecular cyclization of N-benzyl 2-anilinoacetals. Acidic mesoporous molecular sieve (MCM-41-SO3H) has shown excellent catalytic activity on this transformation, and the 2,3-unsubstituted indoles bearing 7-substituent or strong electron-withdrawing substituents also could be achieved by this protocol. Moreover, the heterogeneous catalyst, MCM-41-SO3H, could be conveniently recovered and reused without obvious loss of the catalytic activity. This work will provide an economic and environmental-benign method for the construction of various indole derivatives. (C) 2013 Elsevier Ltd. All rights reserved.