7-methoxy-5-nitro-1H-indole | 180624-23-1

• 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: 7-methoxy-5-nitro-1H-indole
• CAS: 180624-23-1
• 化学式: C₉H₈N₂O₃
• 分子量: 192.174
• InChiKey: FPHHJNSWCMUVBR-UHFFFAOYSA-N

物化性质

• 沸点：
  409.5±25.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methoxy-5-nitro-1H-indole 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 、 copper(l) iodide 氢氧化钾 、 氢气 、 bis(pyridine)iodonium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 20.0 ℃ 、294.18 kPa 条件下， 反应 23.08h， 生成 N-tosyl-5-amino-4-[2-(trimethylsilyl)ethynyl]-7-methoxyindole
  参考文献：
  名称：

  Efficient Reagents for the Synthesis of 5-, 7-, and 5,7-Substituted Indoles Starting from Aromatic Amines:  Scope and Limitations

  摘要：

  Upon reaction with IPy(2)BF(4), 4-substituted anilines give regioselectively the corresponding o-iodoanilines in nearly quantitative yield, in a process that can be carried out on a multigram scale. Palladium-catalyzed coupling of the resulting 2-iodoanilines with (trimethylsilyl)acetylene (TMSA), followed by efficient CuI-mediated nitrogen cyclization onto alkynes with concurrent elimination of the TMS substituent, allows a straightforward elaboration of 5-mono- and 5,7-disubstituted indoles from aromatic amines. This new approach to the aforementioned indoles does not requires protective groups on nitrogen at any step and can be adapted for preparing related 7-manosubstituted indoles. Moreover, examples iterating the process are given, allowing bis-annulation and sequential double annulation and resulting in synthesis of benzodipyrroles. Additionally, suitable conditions for iodination of some of the target indoles with IPy(2)BF(4) are discussed.

  DOI：

  10.1021/jo952119+
• 作为产物：
  描述：

  4-nitro-2-methoxy-6-[2-(trimethylsilyl)ethynyl]aniline 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以60%的产率得到7-methoxy-5-nitro-1H-indole
  参考文献：
  名称：

  Efficient Reagents for the Synthesis of 5-, 7-, and 5,7-Substituted Indoles Starting from Aromatic Amines:  Scope and Limitations

  摘要：

  Upon reaction with IPy(2)BF(4), 4-substituted anilines give regioselectively the corresponding o-iodoanilines in nearly quantitative yield, in a process that can be carried out on a multigram scale. Palladium-catalyzed coupling of the resulting 2-iodoanilines with (trimethylsilyl)acetylene (TMSA), followed by efficient CuI-mediated nitrogen cyclization onto alkynes with concurrent elimination of the TMS substituent, allows a straightforward elaboration of 5-mono- and 5,7-disubstituted indoles from aromatic amines. This new approach to the aforementioned indoles does not requires protective groups on nitrogen at any step and can be adapted for preparing related 7-manosubstituted indoles. Moreover, examples iterating the process are given, allowing bis-annulation and sequential double annulation and resulting in synthesis of benzodipyrroles. Additionally, suitable conditions for iodination of some of the target indoles with IPy(2)BF(4) are discussed.

  DOI：

  10.1021/jo952119+

文献信息

• 一种具有抗肿瘤活性的含吲哚结构的化合物 及其合成方法
  申请人：陕西科技大学

  公开号：CN104230786B

  公开（公告）日：2017-03-22

  本发明公开了结构式（I）所示具有抗肿瘤活性的含吲哚结构的化合物，该类含吲哚结构的化合物以吲哚衍生物、肉桂酰氯和苯肼为原料，通过催化还原方法合成。本发明原料经济易得，合成过程采用一锅法，避免了繁杂的多步操作，操作简便，反应条件温和，收率较好。MTT法进行活性测试研究结果初步显示，该类化合物对多种肿瘤细胞株具有良好的抑制活性，具有较好的医药应用前景。
• Efficient Reagents for the Synthesis of 5-, 7-, and 5,7-Substituted Indoles Starting from Aromatic Amines:  Scope and Limitations
  作者：Jesús Ezquerra、Concepción Pedregal、Carlos Lamas、José Barluenga、Marta Pérez、Miguel Angel García-Martín、José M. González

  DOI：10.1021/jo952119+

  日期：1996.1.1

  Upon reaction with IPy(2)BF(4), 4-substituted anilines give regioselectively the corresponding o-iodoanilines in nearly quantitative yield, in a process that can be carried out on a multigram scale. Palladium-catalyzed coupling of the resulting 2-iodoanilines with (trimethylsilyl)acetylene (TMSA), followed by efficient CuI-mediated nitrogen cyclization onto alkynes with concurrent elimination of the TMS substituent, allows a straightforward elaboration of 5-mono- and 5,7-disubstituted indoles from aromatic amines. This new approach to the aforementioned indoles does not requires protective groups on nitrogen at any step and can be adapted for preparing related 7-manosubstituted indoles. Moreover, examples iterating the process are given, allowing bis-annulation and sequential double annulation and resulting in synthesis of benzodipyrroles. Additionally, suitable conditions for iodination of some of the target indoles with IPy(2)BF(4) are discussed.