1-(5-methyl-2-nitrophenyl)-4,9-dihydro-3H-β-carboline | 885463-80-9

• 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-(5-methyl-2-nitrophenyl)-4,9-dihydro-3H-β-carboline
• 英文别名: 1-(5-methyl-2-nitrophenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole
• CAS: 885463-80-9
• 化学式: C₁₈H₁₅N₃O₂
• 分子量: 305.336
• InChiKey: OQBSKVUISBQACO-UHFFFAOYSA-N

物化性质

• 沸点：
  536.5±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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-(5-methyl-2-nitrophenyl)-4,9-dihydro-3H-β-carboline 在 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 N-[2-(4,9-Dihydro-3H-β-carbolin-1-yl)-4-methyl-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：

  5-甲基-2-硝基苯甲酸 在 phosphorus pentoxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 34.0h， 生成 1-(5-methyl-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

• An efficient and convenient synthesis of heterocycle-fused indazoles via the N–N bond forming reaction of nitroarenes induced by low-valent titanium reagent
  作者：Wei Lin、Ming-Hua Hu、Xian Feng、Cheng-Pao Cao、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1016/j.tet.2013.05.074

  日期：2013.8

  A mild and efficient one-pot protocol for the preparation of 8,13-dihydro-7H-indolo[2′,3′:3,4]pyrido[1,2-b]indazole and 5,6-dihydroindazolo[3,2-a]isoquinoline via the reductive cyclization of nitro-aryl substrates mediated by a low-valent titanium reagent has been developed. The attractive features of the current method include an N–N bond formation and the selective reduction of the CN bond and nitro

  一种温和有效的一锅法制备8,13-dihydro-7 H-吲哚并[2'，3'：3,4]吡啶并[1,2- b ]吲唑和5,6-二氢吲唑[3]已经开发了通过低价钛试剂介导的硝基-芳基底物的还原环化形成的2-2- α ]异喹啉。当前方法的吸引人的特征包括N–N键的形成以及C N键和硝基的选择性还原，通过控制反应混合物的pH值，一锅即可轻松实现。