2-(3-methoxyphenyl)-2-(N-phenylamino)propanenitrile | 1202913-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-methoxyphenyl)-2-(N-phenylamino)propanenitrile
• 英文别名: 2-anilino-2-(3-methoxy-phenyl) propanenitrile
• CAS: 1202913-99-2
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: YOUCDUYEGNWGEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45.05
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  三甲基乙腈 、 苯胺 、 3-甲氧基苯乙酮 在 phenylsulfonic acid(at)silica(at)nano-Fe₃O₄ 作用下， 以 neat (no solvent) 为溶剂， 反应 7.0h， 以89%的产率得到2-(3-methoxyphenyl)-2-(N-phenylamino)propanenitrile
  参考文献：
  名称：

  Magnetic Solid Sulfonic Acid Decorated with Hydrophobic Regulators: A Combinatorial and Magnetically Separable Catalyst for the Synthesis of α-Aminonitriles

  摘要：

  A three-component, Strecker reaction of a series of aldehydes or ketones, amines, and trimethylsilyl cyanide for the synthesis of alpha-aminonitriles in the presence of a catalytic amount of a magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H under solvent-free conditions have been investigated. This catalyst, with a combination of hydrophobicity and acidity on the Fe3O4@SiO2 core-shell of the magnetic nanobeads, as well as its water-resistant property, enabled easy mass transfer and catalytic activity in the Strecker reaction. The catalyst was easily separated by an external magnet and the recovered catalyst was reused in 6 successive reaction cycles without any significant loss of activity.

  DOI：

  10.1021/co500022g

文献信息

• Zr(HSO4)4 catalyzed one-pot strecker synthesis of α-amino nitriles from aldehydes and ketones under solvent-free conditions
  作者：A. R. Hajipour、Y. Ghayeb、N. Sheikhan

  DOI：10.1007/bf03246031

  日期：2010.6

  A mild and efficient method has been developed for the preparation of α-amino nitriles from the condensation of aldehydes and ketones with aniline and TMSCN in the presence of a catalytic amount of Zr(HSO4)4 under solvent-free conditions at room temperature.

  已经开发了一种温和有效的方法，在室温下在无溶剂条件下，在催化量的Zr（HSO 4）4存在下，由醛和酮与苯胺和TMSCN缩合制备α-氨基腈。
• Solvent-free three component Strecker reaction of ketones using highly recyclable and hydrophobic sulfonic acid based nanoreactors
  作者：Babak Karimi、Daryoush Zareyee

  DOI：10.1039/b911388f

  日期：——

  An efficient and environmentally benign system was developed for the one-pot three-component Strecker reaction of ketones under solvent-free conditions, with the use of a highly recoverable SBA-15 supported sulfonic acid. Also findings concerning the effects of functionalized inert groups and silica backbone pore size on substrate scope, catalytic activity and recycling behavior of the catalysts were briefly discussed. The simple experimental and product isolation procedure accompanied by easy recovery and reusability of the catalyst could be considered as attractive features of this new protocol which will hopefully develop a clean strategy for the synthesis of α-amino nitriles.

  通过使用高回收率的 SBA-15 支承磺酸，开发出了一种高效且对环境无害的系统，用于在无溶剂条件下进行酮类化合物的一锅三组分 Strecker 反应。此外，还简要讨论了官能化惰性基团和二氧化硅骨架孔径对底物范围、催化活性和催化剂回收行为的影响。实验和产物分离过程简单，催化剂易于回收和重复使用，这些都是这一新方案的诱人之处，有望为 α-氨基腈的合成开发出一种清洁的策略。