1-(4-chloro-2-nitrophenyl)-4,9-dihydro-3H-β-carboline | 885463-85-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(4-chloro-2-nitrophenyl)-4,9-dihydro-3H-β-carboline
• 英文别名: 1-(4-chloro-2-nitrophenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole
• CAS: 885463-85-4
• 化学式: C₁₇H₁₂ClN₃O₂
• 分子量: 325.754
• InChiKey: WKWNXOZWBBBFDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-chloro-2-nitrophenyl)-4,9-dihydro-3H-β-carboline 在 苯硫酚 、 三乙胺 、 对甲苯磺酰氯 、 tin(ll) chloride 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 9-chloro-5,12-dihydro-6H-6a,7,12-triaza-indeno[1,2-a]fluorene
  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：

  4-chloro-N-[2-(1H-indol-3-yl)ethyl]-2-nitrobenzamide 在 phosphorus pentoxide 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以70%的产率得到1-(4-chloro-2-nitrophenyl)-4,9-dihydro-3H-β-carboline
  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.