2-phenyl-2-{[(S)-1-phenylethyl]amino} acetonitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-phenyl-2-{[(S)-1-phenylethyl]amino} acetonitrile
• 英文别名: 2-phenyl-2-[[(1S)-1-phenylethyl]amino]acetonitrile
• 化学式: C₁₆H₁₆N₂
• 分子量: 236.316
• InChiKey: RPNGOJFQSLRIMM-KNVGNIICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-2-{[(S)-1-phenylethyl]amino} acetonitrile 在 硫酸 、 水 作用下， 反应 12.0h， 以52%的产率得到(S)-2-phenyl-2-((S)-1-phenylethylamino)acetamide
  参考文献：
  名称：

  二氧化碳促进的三组分斯特雷克反应

  摘要：

  醛、胺和 KCN 的三组分 Strecker 反应首次在超临界二氧化碳中进行。在提议的程序中，无毒和不可燃的二氧化碳不仅作为一种环境友好的反应介质，而且作为反应促进剂通过原位碳酸的形成使真正的氰化剂 (HCN) 从可用的 KCN 中逐渐释放出来。优化反应条件（压力、温度和试剂浓度），将各种芳香族和脂肪族胺和醛转化为有价值的α-氨基腈，包括预期的药理物质。使用等摩尔量的氰试剂，在“绿色”溶剂介质中在温和条件（90 bar，35°C）下在密封高压釜中进行该过程以及产品的高产率和所开发程序的可扩展性使其成为适用于可持续的工业应用。

  DOI：

  10.1039/d1gc03161a
• 作为产物：
  描述：

  三甲基氰硅烷 、 N-benzylidene-(S)-α-methylbenzylamine 在 ((2,6-bis(N-cyclohexyl)imino)phenyl)aquoplatinum(II) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-phenyl-2-{[(S)-1-phenylethyl]amino} acetonitrile
  参考文献：
  名称：

  Catalysis of aldehyde and imine silylcyanation by platinum and palladium NCN-pincer complexes

  摘要：

  The room temperature addition of trimethylsilylcyanide to aromatic and aliphatic aldehydes to give the corresponding cyanohydrins is efficiently catalysed by 1 mol% of ((2,6-bis(N-cyclohexyl)imino)phenyl)aquoplatinum(II) trifluoromethanesulfonate 1a. This methodology is also applicable to the addition of trimethylsilylcyanide to Schiff bases resulting in the formation of alpha-amino nitriles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.201

文献信息

• Cu(OTf)2 or Et3N-catalyzed three-component condensation of aldehydes, amines and cyanides: a high yielding synthesis of α-aminonitriles
  作者：Abhimanyu S. Paraskar、Arumugam Sudalai

  DOI：10.1016/j.tetlet.2006.06.008

  日期：2006.8

  Copper(II) triflate or Et3N have been found to catalyze, under ambient conditions, the addition of a cyanide anion, such as trimethylsilyl cyanide or acetone cyanohydrin, onto in situ generated imines, furnishing α-aminonitriles in excellent yields.

  已发现三氟甲磺酸铜（II）或Et 3 N在环境条件下催化在原位生成的亚胺上添加氰化物阴离子（如三甲基甲硅烷基氰化物或丙酮氰醇），从而以优异的产率提供α-氨基腈。
• Highly efficient three-component Strecker-type reaction catalyzed by MgI 2 etherate under solvent-free conditions
  作者：Pengcheng Li、Yongdong Zhang、Zhili Chen、Xingxian Zhang

  DOI：10.1016/j.tetlet.2017.03.087

  日期：2017.5

  A concise, straightforward and efficient method has been developed for the synthesis of α-aminonitriles by an one-pot three-component condensation of aldehydes or ketones, amines and trimethylsilyl cyanide catalyzed by MgI2 etherate under solvent-free conditions. This protocol has some advantages such as mild reaction condition, simple work-up, short reaction time and high product yields.

  已经开发出一种简洁，直接，有效的方法，用于在无溶剂条件下通过MgI 2醚化物催化的一锅三组分缩合醛或酮，胺和三甲基甲硅烷基氰化物来合成α-氨基腈。该方案具有一些优点，例如反应条件温和，后处理简单，反应时间短和产物产率高。
• One-pot, solvent-free synthesis of α-aminonitriles under catalysis by magnesium bromide ethyl etherate
  作者：Mohammad M Mojtahedi、M Saeed Abaee、Hassan Abbasi

  DOI：10.1139/v06-024

  日期：2006.3.1

  the synthesis of α-aminonitriles from aldehydes, amines, and trimethylsilyl cyanide using a catalytic amount of magnesium bromide ethyl etherate in the absence of solvent. Rapid formation of products is observed at room temperature in a one-pot procedure under very mild conditions giving excellent yields of the title compounds.Key words: catalyzed Strecker's reaction, α-aminonitriles, magnesium bromide

  已经开发了一种三组分、高效且简便的方法，用于在没有溶剂的情况下，使用催化量的溴化镁乙基醚合物从醛、胺和三甲基氰基氰化物合成 α-氨基腈。在非常温和的条件下，在室温下在一锅法中观察到产物的快速形成，标题化合物的产率很高。关键词：催化斯特雷克反应，α-氨基腈，溴化镁，无溶剂。
• Superparamagnetic iron oxide as an efficient catalyst for the one-pot, solvent-free synthesis of α-aminonitriles
  作者：Mohammad M. Mojtahedi、M. Saeed Abaee、Tooba Alishiri

  DOI：10.1016/j.tetlet.2009.02.199

  日期：2009.5

  Superparamagnetic Fe3O4 is shown to act as a very efficient catalyst for the one-pot, three-component synthesis of alpha-aminonitriles from aldehydes, amines, and TMSCN. The catalyst is easily recovered by the use of an external magnet and reused in several reactions without any noticeable loss of activity. The products are obtained rapidly at room temperature in good purity upon separation of the catalyst and evaporation of the volatiles of the reaction mixture. (C) 2009 Elsevier Ltd. All rights reserved.
• Catalysis of aldehyde and imine silylcyanation by platinum and palladium NCN-pincer complexes
  作者：John S Fossey、Christopher J Richards

  DOI：10.1016/j.tetlet.2003.09.201

  日期：2003.12

  The room temperature addition of trimethylsilylcyanide to aromatic and aliphatic aldehydes to give the corresponding cyanohydrins is efficiently catalysed by 1 mol% of ((2,6-bis(N-cyclohexyl)imino)phenyl)aquoplatinum(II) trifluoromethanesulfonate 1a. This methodology is also applicable to the addition of trimethylsilylcyanide to Schiff bases resulting in the formation of alpha-amino nitriles. (C) 2003 Elsevier Ltd. All rights reserved.