3-[2-(2-nitrophenylcarboxamido)ethyl]-1H-indole | 33405-85-5

• 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: 3-[2-(2-nitrophenylcarboxamido)ethyl]-1H-indole
• 英文别名: N-[2-(1H-indol-3-yl)ethyl]-2-nitrobenzamide；N-(2-indol-3-yl-ethyl)-2-nitro-benzamide；2-nitro-benzoic acid-(2-indol-3-yl-ethylamide)；2-Nitro-benzoesaeure-(2-indol-3-yl-aethylamid)；N-o-Nitrobenzoyltryptamin
• CAS: 33405-85-5
• 化学式: C₁₇H₁₅N₃O₃
• 分子量: 309.324
• InChiKey: HYRDPSCBCZDNDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 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：

  3-[2-(2-nitrophenylcarboxamido)ethyl]-1H-indole 在 phosphorus pentoxide 、 苯硫酚 、 三乙胺 、 对甲苯磺酰氯 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 8.5h， 生成 8,13-dihydro-7H-indolo[2',3':3,4]pyrido[1,2-b]indazole
  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 、 邻硝基苯甲酸 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 32.0h， 以95%的产率得到3-[2-(2-nitrophenylcarboxamido)ethyl]-1H-indole
  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

• Synthesis of New β-Carboline Derivatives via 1,7-Electrocyclisation of Azomethine Ylides
  作者：Miklós Nyerges、Andrea Virányi、Judit Tóth、Gábor Blaskó、László Tőke

  DOI：10.1055/s-2006-926400

  日期：2006.4

  A new route to the benzo[5,6]azepino[2,1-a]-β-carboline and indazolo[3,2-a]-β-carboline ring systems has been developed via the 1,7-dipolar electrocyclisation reactions of azomethine ylides derived from easily available β-carboline derivatives.

  通过对易于获得的δ-咔啉衍生物中的偶氮甲基酰化物进行 1,7 双极电环化反应，开发出了一条通向苯并[5,6]氮杂卓[2,1-a]-δ-咔啉和吲唑并[3,2-a]-δ-咔啉环系统的新途径。
• An Alternative to Pictet-Gams Reaction Triggered by Hendrickson Reagent: Isoquinolines and β-Carbolines from Amides
  作者：Shaozhong Wang、Mengde Wu

  DOI：10.1055/s-0029-1217138

  日期：2010.2

  The Hendrickson reagent derived from triflic anhydride and triphenylphosphine oxide exhibited high oxophilicity and induced the intramolecular cyclization of β-arylethylamides perfectly. Thus, a one-pot protocol to access isoquinoline and β-carboline was developed involving cyclization followed by oxidative aromatization. Hendrickson reagent - isoquinoline - β-carboline - β-arylethylamide - manganese(IV)

  衍生自三氟甲磺酸酐和三苯基氧化膦的亨德里克森试剂表现出高的亲氧性，并完美地诱导了β-芳基乙酰胺的分子内环化。因此，开发了一种一锅法访问异喹啉和β-咔啉，该方法涉及环化，然后进行氧化芳构化。 亨德里克森试剂-异喹啉-β-咔啉-β-芳基乙酰胺-氧化锰
• Asahina; Ishimasa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1926, p. 62
  作者：Asahina、Ishimasa

  DOI：——

  日期：——