1,3-diamino-6-methyl-2,4-bis[2-(trimethylsilyl)ethynyl]benzene

• 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: 1,3-diamino-6-methyl-2,4-bis[2-(trimethylsilyl)ethynyl]benzene
• 英文别名: 4-Methyl-2,6-bis(2-trimethylsilylethynyl)benzene-1,3-diamine
• 化学式: C₁₇H₂₆N₂Si₂
• 分子量: 314.578
• InChiKey: OXTLHRSCGPKAQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-diamino-6-methyl-2,4-bis[2-(trimethylsilyl)ethynyl]benzene 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以30%的产率得到5-methyl-1,6-dihydrobenzo[1,2-b:3,4-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：

  2,4-二氨基甲苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide bis(pyridine)iodonium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 生成 1,3-diamino-6-methyl-2,4-bis[2-(trimethylsilyl)ethynyl]benzene
  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

• 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.