α-(hexylamino)-benzeneacetonitrile | 154319-59-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: α-(hexylamino)-benzeneacetonitrile
• 英文别名: N-n-Hexyl-α-cyanobenzylamine；2-(Hexylamino)-2-phenylacetonitrile
• CAS: 154319-59-2
• 化学式: C₁₄H₂₀N₂
• mdl: MFCD24389205
• 分子量: 216.326
• InChiKey: GIJFKGDSAGQJMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  苯甲酰氯 、 α-(hexylamino)-benzeneacetonitrile 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 N-[cyano(phenyl)methyl]-N-hexylbenzamide
  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：

  正己胺 、 三甲基氰硅烷 、 苯甲醛 在 azaphosphatrane salt on Merrifield resin 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以99%的产率得到α-(hexylamino)-benzeneacetonitrile
  参考文献：
  名称：

  [HP(HNCH2CH2)3N]NO3: an efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions

  摘要：

  In the presence of a catalytic amount of an azaphosphatrane nitrate salt, amines and thiols react readily with Michael acceptors. The salt is also an efficient promoter for the one pot synthesis of alpha-amino and alpha-amidonitriles. By anchoring the salt to Merrifield Resin, a reusable heterogeneous catalyst is obtained for these reactions. Evidence is presented for catalysis being attributable solely to the NO3- ion. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.117

文献信息

• [HP(HNCH2CH2)3N]NO3: an efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions
  作者：Brandon M. Fetterly、Nirmal K. Jana、John G. Verkade

  DOI：10.1016/j.tet.2005.09.117

  日期：2006.1

  In the presence of a catalytic amount of an azaphosphatrane nitrate salt, amines and thiols react readily with Michael acceptors. The salt is also an efficient promoter for the one pot synthesis of alpha-amino and alpha-amidonitriles. By anchoring the salt to Merrifield Resin, a reusable heterogeneous catalyst is obtained for these reactions. Evidence is presented for catalysis being attributable solely to the NO3- ion. (c) 2005 Elsevier Ltd. All rights reserved.
• Open-Chain Reissert Compounds: One-Pot Synthesis and Utility in Synthesis of Unsymmetrical Imides, .alpha.-Acylamino Carboxamides, Imidazolinones, and Hydantoins
  作者：Jean-Pierre Leblanc、Harry W. Gibson

  DOI：10.1021/jo00084a025

  日期：1994.3

  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.