N-(2-Phenethyl)-α-cyanobenzylamine | 1564-19-8

• 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: N-(2-Phenethyl)-α-cyanobenzylamine
• 英文别名: 2-(phenylethylamino)-2-phenylacetonitrile；N-Phenylethylamino-phenylacetonitril；2-Phenaethylamino-2-phenyl-acetonitril；phenethylamino-phenyl-acetonitrile；2-(Phenethylamino)-2-phenyl-acetonitrile；2-phenyl-2-(2-phenylethylamino)acetonitrile
• CAS: 1564-19-8
• 化学式: C₁₆H₁₆N₂
• 分子量: 236.316
• InChiKey: UFTCLJPFCVHRNP-UHFFFAOYSA-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：
  5
• 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：

  N-(2-Phenethyl)-α-cyanobenzylamine 在 双氧水 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 4-Phenyl-3-(2-phenethyl)hydantoin
  参考文献：
  名称：

  Open-Chain Reissert Compounds: One-Pot Synthesis and Utility in Synthesis of Unsymmetrical Imides, .alpha.-Acylamino Carboxamides, Imidazolinones, and Hydantoins

  摘要：

  Acyclic Reissert compounds 2 and bis(Reissert compound)s 3-5 can be conveniently prepared in a biphasic system without isolation of the intermediate cr-amino nitriles. Treatment of 2 with sodium hydride affords substituted unsymmetrical imides such as 8. Oxidative hydrolysis of 2 by hydrogen peroxide converts the nitrile groups to primary amides, giving acyl derivatives of alpha-amino carboxamides 9, whereas substituted analogs 7 undergo cyclization to imidazolinones 11. Hydrogen peroxide treatment of alpha-cyano carbamate Reissert compounds, substituted (13) or not (12), affords substituted hydantoins 14.

  DOI：

  10.1021/jo00084a025
• 作为产物：
  描述：

  氰化钠 、 苯甲醛 、 2-苯乙胺 生成 N-(2-Phenethyl)-α-cyanobenzylamine
  参考文献：
  名称：

  Open-Chain Reissert Compounds: One-Pot Synthesis and Utility in Synthesis of Unsymmetrical Imides, .alpha.-Acylamino Carboxamides, Imidazolinones, and Hydantoins

  摘要：

  Acyclic Reissert compounds 2 and bis(Reissert compound)s 3-5 can be conveniently prepared in a biphasic system without isolation of the intermediate cr-amino nitriles. Treatment of 2 with sodium hydride affords substituted unsymmetrical imides such as 8. Oxidative hydrolysis of 2 by hydrogen peroxide converts the nitrile groups to primary amides, giving acyl derivatives of alpha-amino carboxamides 9, whereas substituted analogs 7 undergo cyclization to imidazolinones 11. Hydrogen peroxide treatment of alpha-cyano carbamate Reissert compounds, substituted (13) or not (12), affords substituted hydantoins 14.

  DOI：

  10.1021/jo00084a025

文献信息

• Strecker reactions with hexacyanoferrates as non-toxic cyanide sources
  作者：Caroline Grundke、Till Opatz

  DOI：10.1039/c9gc00720b

  日期：——

  The Strecker reaction is the most widely applied three-component reaction. Although highly useful for the preparation of α-amino nitriles, α-amino acids, hydantoins and numerous related compounds, the need for the application of toxic sources of HCN limits its application in both academic and industrial settings. Here, we present a facile protocol for Strecker reactions using a mixture of potassium

  斯特雷克反应是应用最广泛的三组分反应。尽管对于制备α-氨基腈，α-氨基酸，乙内酰脲和许多相关化合物非常有用，但是需要使用HCN的有毒来源限制了它在学术和工业环境中的应用。在这里，我们提出了一种简便的方案，可使用亚铁氰化钾和亚铁氰化钾的混合物作为无毒替代物进行Strecker反应。
• Synthesis of Highly Substituted Unsymmetrical 1,2-Diamines, 1,2-Diimines, Imidazolium Salts and Imidazolylidenes by Aldimine Cross-Coupling
  作者：Till Opatz、Coralie Kison

  DOI：10.1055/s-2006-950237

  日期：2006.11

  compounds can directly be oxidized to 1,2-diimines or reduced to 1,2-diamines in a one-pot reaction. 1,2-Diamines can be obtained in high diastereoselectivity by reduction of the 1,2-diimines. In this case, the relative configuration of the products can be chosen depending on the reduction conditions. Cyclization of the unsymmetrical diimines with halomethyl ethers or esters leads to 1,3,4,5-tetrasubstituted

  衍生自芳香醛和伯胺的 α-氨基腈可以在不使用保护基团的情况下定量去质子化。所得稳定化的 α-氨基碳负离子与亚胺的 1,2-加成产生 α-氨基亚胺和互变异构的烯二胺。这些不稳定的化合物可以直接氧化成 1,2-二亚胺或在一锅反应中还原成 1,2-二胺。通过还原 1,2-二亚胺可以高非对映选择性获得 1,2-二胺。在这种情况下，可以根据还原条件选择产品的相对配置。不对称二亚胺与卤代甲基醚或酯的环化产生 1,3,4,5-四取代咪唑鎓盐，可作为制备高度取代的亲核卡宾的原料。
• One-Pot Synthesis of Trisubstituted 1,2-Amino Alcohols from Deprotonated α-Amino Nitriles
  作者：Coralie Kison、Till Opatz

  DOI：10.1002/ejoc.200701205

  日期：2008.6

  A short synthesis of N,1,2-trisubstituted vicinal amino alcohols by 1,2-addition of deprotonated N-monosubstituted α-amino nitriles to aldehydes and subsequent one-pot reduction of the intermediates with borane–THF is described. This procedure leads to the predominant formation of the anti-configured products. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  描述了通过去质子化的 N-单取代的 α-氨基腈与醛的 1,2-加成以及随后用硼烷-THF 对中间体进行一锅还原来快速合成 N,1,2-三取代的邻氨基醇。这个过程导致反配置产品的主要形成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Modular Synthesis of Tetrasubstituted Imidazoles and Trisubstituted Oxazoles by Aldimine Cross-Coupling
  作者：Coralie Kison、Till Opatz

  DOI：10.1002/chem.200802175

  日期：2009.1.12

  From five to two: The addition of deprotonated Strecker products to N‐acylimines permits the synthesis of tetrasubstituted imidazoles or trisubstituted oxazoles in three or four steps, respectively. In total, the target compounds are prepared from two aldehydes, a primary amine, an acid chloride and ammonia (see scheme).

  从5到2：向N-嘧啶中添加去质子化的Strecker产品可以分别通过三步或四步合成四取代的咪唑或三取代的恶唑。总而言之，目标化合物是由两种醛（伯胺，酰氯和氨）制得的（请参见方案）。
• An Aldimine Cross-Coupling for the Diastereoselective Synthesis of Unsymmetrical 1,2-Diamines
  作者：Coralie Kison、Nino Meyer、Till Opatz

  DOI：10.1002/anie.200501705

  日期：2005.9.5

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