2-[[Cyano(phenyl)methyl]amino]benzonitrile | 1107636-99-6

• 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: 2-[[Cyano(phenyl)methyl]amino]benzonitrile
• CAS: 1107636-99-6
• 化学式: C₁₅H₁₁N₃
• 分子量: 233.272
• InChiKey: HTSFSZPKIUDLFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  59.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[[Cyano(phenyl)methyl]amino]benzonitrile 、 苯甲酰氯 在 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以87%的产率得到N-(1-benzoyl-2-cyano-2-phenylindol-3-ylidene)benzamide
  参考文献：
  名称：

  Synthesis of 3-aminoindole derivatives: combination of Thorpe–Ziegler cyclization and unexpected allylindium-mediated decyanation

  摘要：

  alpha-Anilinonitriles were unexpectedly converted to 3-iminodihydroindoles via the Thorpe-Ziegler cyclization during the benzoylation. 3-Iminodihydroindoles were transformed to 3-aminoindoles in good yields via an allylindium-mediated decyanative aromatization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.085
• 作为产物：
  描述：

  扁桃腈 、 2-氨基苯甲腈 以 乙醇 为溶剂， 反应 30.0h， 以65%的产率得到2-[[Cyano(phenyl)methyl]amino]benzonitrile
  参考文献：
  名称：

  Synthesis of 3-aminoindole derivatives: combination of Thorpe–Ziegler cyclization and unexpected allylindium-mediated decyanation

  摘要：

  alpha-Anilinonitriles were unexpectedly converted to 3-iminodihydroindoles via the Thorpe-Ziegler cyclization during the benzoylation. 3-Iminodihydroindoles were transformed to 3-aminoindoles in good yields via an allylindium-mediated decyanative aromatization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.085

文献信息

• Trifluoroethanol as a metal-free, homogeneous and recyclable medium for the efficient one-pot synthesis of α-amino nitriles and α-amino phosphonates
  作者：Akbar Heydari、Samad Khaksar、Mahmood Tajbakhsh

  DOI：10.1016/j.tetlet.2008.10.106

  日期：2009.1

  Trifluoroethanol is found to be an efficient and recyclable medium in promoting one-pot, three-component coupling reactions of aldehydes or ketones, amines and trimethylsilyl cyanide or trimethyl phosphite to afford the corresponding α-amino nitriles or α-amino phosphonates in high yields. This protocol does not require the use of an acid or base catalyst.

  发现三氟乙醇是促进醛或酮，胺和三甲基甲硅烷基氰化物或亚磷酸三甲酯的一锅，三组分偶联反应的有效且可循环的介质，以高收率提供相应的α-氨基腈或α-氨基膦酸酯。该方案不需要使用酸或碱催化剂。
• Synthesis of 3-aminoindole derivatives: combination of Thorpe–Ziegler cyclization and unexpected allylindium-mediated decyanation
  作者：Yu Mi Kim、Ko Hoon Kim、Sunhong Park、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2011.01.085

  日期：2011.3

  alpha-Anilinonitriles were unexpectedly converted to 3-iminodihydroindoles via the Thorpe-Ziegler cyclization during the benzoylation. 3-Iminodihydroindoles were transformed to 3-aminoindoles in good yields via an allylindium-mediated decyanative aromatization. (C) 2011 Elsevier Ltd. All rights reserved.