4-chloro-N-[2-(1H-indol-3-yl)ethyl]-2-nitrobenzamide | 885463-77-4

• 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: 4-chloro-N-[2-(1H-indol-3-yl)ethyl]-2-nitrobenzamide
• CAS: 885463-77-4
• 化学式: C₁₇H₁₄ClN₃O₃
• 分子量: 343.769
• InChiKey: SXVSFCUPVFICBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-N-[2-(1H-indol-3-yl)ethyl]-2-nitrobenzamide 在 phosphorus pentoxide 、 苯硫酚 、 三乙胺 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 8.25h， 生成 N-[5-Chloro-2-(4,9-dihydro-3H-β-carbolin-1-yl)-phenyl]-hydroxylamine
  参考文献：
  名称：

  Unprecedented SnCl₂-Mediated Cyclization of Nitro Arenes via N−N Bond Formation

  摘要：

  A mild, efficient, one-pot protocol for the cyclization of nitro-aryl substrates using SnCl2 has been described. The mechanistic course of the reaction suggests the involvement of a hydroxylamine intermediate leading to an intramolecular cyclization via N-N bond formation. The versatility of the methodology has been demonstrated by using two nitro-aryl substrates derived from dihydroisoquinolines and dihydro-beta-carbolines. The intramolecular cyclization led to the formation of indazoles in high yields and purities.

  DOI：

  10.1021/ol053033y
• 作为产物：
  描述：

  色胺 、 4-氯-2-硝基苯甲酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以89%的产率得到4-chloro-N-[2-(1H-indol-3-yl)ethyl]-2-nitrobenzamide
  参考文献：
  名称：

  Unprecedented SnCl₂-Mediated Cyclization of Nitro Arenes via N−N Bond Formation

  摘要：

  A mild, efficient, one-pot protocol for the cyclization of nitro-aryl substrates using SnCl2 has been described. The mechanistic course of the reaction suggests the involvement of a hydroxylamine intermediate leading to an intramolecular cyclization via N-N bond formation. The versatility of the methodology has been demonstrated by using two nitro-aryl substrates derived from dihydroisoquinolines and dihydro-beta-carbolines. The intramolecular cyclization led to the formation of indazoles in high yields and purities.

  DOI：

  10.1021/ol053033y

文献信息

• Unprecedented SnCl₂-Mediated Cyclization of Nitro Arenes via N−N Bond Formation
  作者：Devesh Sawant、Rishi Kumar、Prakas R. Maulik、Bijoy Kundu

  DOI：10.1021/ol053033y

  日期：2006.4.1

  A mild, efficient, one-pot protocol for the cyclization of nitro-aryl substrates using SnCl2 has been described. The mechanistic course of the reaction suggests the involvement of a hydroxylamine intermediate leading to an intramolecular cyclization via N-N bond formation. The versatility of the methodology has been demonstrated by using two nitro-aryl substrates derived from dihydroisoquinolines and dihydro-beta-carbolines. The intramolecular cyclization led to the formation of indazoles in high yields and purities.