N-(2-硝基苯)-5-硝基吲哚 | 1045601-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: N-(2-硝基苯)-5-硝基吲哚
• 英文名称: N-(2-nitrobenzene)-5-nitroindole
• 英文别名: 5-Nitro-1-(2-nitrophenyl)indole；5-nitro-1-(2-nitrophenyl)indole
• CAS: 1045601-61-3
• 化学式: C₁₄H₉N₃O₄
• 分子量: 283.243
• InChiKey: CLSUZZXMQMPSKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-硝基吲哚 、 硝基氯苯 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以50%的产率得到N-(2-硝基苯)-5-硝基吲哚
  参考文献：
  名称：

  Ultrasound-Assisted N-Arylation of Indoles without any Catalyst

  摘要：

  An efficient method for the ultrasound-assisted N-arylation of indoles with haloarenes in an air atmosphere mediated by CS2CO3 without any catalyst is reported. N-arylindoles are obtained in moderate to good yields while indoles cross-coupling with activated aryl halides (X = F or Cl).

  DOI：

  10.3987/com-07-s(n)1

文献信息

• Synthesis and HIV-1 Integrase Inhibition Activity of some N-Arylindoles
  作者：Hui Xu、Wu-Qing Liu、Ling-Ling Fan、Yang Chen、Liu-Meng Yang、Lei Lv、Yong-Tang Zheng

  DOI：10.1248/cpb.56.720

  日期：——

  Eight simple N-arylindoles were designed, synthesized and evaluated as human immunodeficiency virus (HIV)-1 integrase inhibitors in vitro for the first time. Among these compounds, 3b, 3e and 3g demonstrated significant anti-HIV-1 integrase activity. Especially 3b showed the highest anti-HIV-1 integrase activity with EC50 value of 7.88 μg/ml and TI value of 24.61. Meantime, some structure–activity relationships were also observed and will provide a new lead for design and discovery of more potent N-arylindoles as HIV-1 integrase inhibitors.

  研究人员设计、合成了八个简单的 N-芳基吲哚，并首次在体外将其作为人类免疫缺陷病毒（HIV）-1 整合酶抑制剂进行了评估。在这些化合物中，3b、3e 和 3g 具有显著的抗 HIV-1 整合酶活性。其中，3b的EC50值为7.88 μg/ml，TI值为24.61，具有最高的抗HIV-1整合酶活性。同时，还观察到了一些结构-活性关系，这将为设计和发现更强的 N-芳基吲哚作为 HIV-1 整合酶抑制剂提供新的线索。
• One-Pot N-Arylation of Indoles Directly from N-Arylsulfonylindoles via Consecutive Deprotection and SNAr Reactions with Activated Aryl Halides
  作者：Hui Xu、Ling-Ling Fan

  DOI：10.1248/cpb.57.321

  日期：——

  involves the consecutive deprotection of N-arylsulfonylindoles as latent indoles and subsequent S(N)Ar reactions with activated aryl halides. This tandem reaction affords an efficient and convenient preparation of N-arylindoles that benefit from prior indoles protection by arylsulfonyl group, and can shorten a reaction sequence and improve synthetic efficiency.

  已经开发了以中等至良好的产率开发一种有效的一步法t-BuOK介导的N-芳基吲哚合成方法。该协议涉及作为潜在的吲哚的N-芳基磺酰吲哚的连续脱保护和随后与活化的芳基卤化物的S（N）Ar反应。该串联反应提供了N-芳基吲哚的有效和方便的制备，该N-芳基吲哚得益于先前通过芳基磺酰基进行的吲哚保护，并且可以缩短反应顺序并提高合成效率。
• Xu, Hui; Fan, Ling-Ling, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2008, vol. 63, # 3, p. 298 - 302
  作者：Xu, Hui、Fan, Ling-Ling

  DOI：——

  日期：——
• Ultrasound-Assisted N-Arylation of Indoles without any Catalyst
  作者：Hui Xu、Lei Lv、Ling-ling Fan、Xiao-qiang He

  DOI：10.3987/com-07-s(n)1

  日期：——

  An efficient method for the ultrasound-assisted N-arylation of indoles with haloarenes in an air atmosphere mediated by CS2CO3 without any catalyst is reported. N-arylindoles are obtained in moderate to good yields while indoles cross-coupling with activated aryl halides (X = F or Cl).