2-(4-chlorobenzylideneamino)acetonitrile | 95730-58-8

• 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-(4-chlorobenzylideneamino)acetonitrile
• 英文别名: 2-[(4-Chlorophenyl)methylideneamino]acetonitrile
• CAS: 95730-58-8
• 化学式: C₉H₇ClN₂
• 分子量: 178.621
• InChiKey: NFOSJXOGNXPWFJ-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  290.6±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  36.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorobenzylideneamino)acetonitrile 在 硼烷四氢呋喃络合物 、 silver(I) acetate 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.17h， 生成 [(2S,3R)-2-(4-chlorophenyl)pyrrolidin-3-yl]methanol
  参考文献：
  名称：

  Synthesis of β -prolinols via [3+2] cycloaddition and one-pot programmed reduction: Valuable building blocks for polyheterocycles

  摘要：

  A novel two-step synthesis of multisubstituted beta-prolinols has been developed, featuring a [3+2] cycloaddition of azomethine ylides and a programmed reduction triggered by the combination of borane and lithium aluminum hydride (LAH). beta-Prolinols are shown to be valuable building blocks for polyheterocycles. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.11.035
• 作为产物：
  描述：

  苯甲醛 在 三乙胺 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 氘代氯仿 、 乙醇 为溶剂， 反应 3.17h， 生成 2-(4-chlorobenzylideneamino)acetonitrile
  参考文献：
  名称：

  Silver-catalyzed dynamic systemic resolution of α-iminonitriles in a 1,3-dipolar cycloaddition process

  摘要：

  一种银催化的动态偶氮甲基亚胺系统在串联环加成反应中被动力学分辨，产生一种独特的吡咯烷产物。

  DOI：

  10.1039/c4cc00944d

文献信息

• 2-Aryl-1,9-dihydrochromeno[3,2-d]imidazoles: a facile synthesis from salicylaldehydes and arylideneaminoacetonitrile
  作者：Marta Costa、Fernanda Proença

  DOI：10.1016/j.tet.2011.01.035

  日期：2011.3

  2-Aryl-1,9-dihydrochromeno[3,2-d]imidazoles were prepared by a one-pot cascade reaction involving salicylaldehydes and arylideneaminoacetonitriles. These novel compounds were isolated in 11-95% yield after reflux in ethanol and triethylamine. A dimeric structure was also identified and partially evolved to the tricyclic product in DMSO solution, according to an evolution study by H-1 NMR spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of β -prolinols via [3+2] cycloaddition and one-pot programmed reduction: Valuable building blocks for polyheterocycles
  作者：Jundong Li、Na Lin、Lei Yu、Yandong Zhang

  DOI：10.1016/j.tetlet.2016.11.035

  日期：2016.12

  A novel two-step synthesis of multisubstituted beta-prolinols has been developed, featuring a [3+2] cycloaddition of azomethine ylides and a programmed reduction triggered by the combination of borane and lithium aluminum hydride (LAH). beta-Prolinols are shown to be valuable building blocks for polyheterocycles. (C) 2016 Elsevier Ltd. All rights reserved.
• Silver-catalyzed dynamic systemic resolution of α-iminonitriles in a 1,3-dipolar cycloaddition process
  作者：Lei Hu、Olof Ramström

  DOI：10.1039/c4cc00944d

  日期：——

  A silver-catalyzed dynamic azomethine ylide system was kinetically resolved in a tandem cycloaddition process, yielding an exclusive pyrrolidine product.

  一种银催化的动态偶氮甲基亚胺系统在串联环加成反应中被动力学分辨，产生一种独特的吡咯烷产物。