N-tosyl-5-amino-4-[2-(trimethylsilyl)ethynyl]-7-methoxyindole | 180624-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-tosyl-5-amino-4-[2-(trimethylsilyl)ethynyl]-7-methoxyindole
• 英文别名: N-tosyl-5-amino-7-methoxy-4-indolyltrimethylsilylacetylene；7-methoxy-1-(4-methylphenyl)sulfonyl-4-(2-trimethylsilylethynyl)indol-5-amine
• CAS: 180624-05-9
• 化学式: C₂₁H₂₄N₂O₃SSi
• 分子量: 412.585
• InChiKey: IRYUSXRMSURHDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  82.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tosyl-5-amino-4-[2-(trimethylsilyl)ethynyl]-7-methoxyindole 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 以45%的产率得到4-methoxy-3-tosyl-3,6-dihydrobenzo[1,2-b:4,3-b']dipyrrole
  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 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 、 copper(l) iodide 氢氧化钾 、 copper(l) iodide 、 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 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、294.18 kPa 条件下， 反应 25.58h， 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+