N-benzyl 2-amino-3,3-dimethyl butyronitrile

• 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-benzyl 2-amino-3,3-dimethyl butyronitrile
• 英文别名: 2-(Benzylamino)-3,3-dimethylbutanenitrile
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: NQEXMNYCHAHCKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-benzyl 2-amino-3,3-dimethyl butyronitrile 在 Oxone 、 四丁基溴化铵 、 碳酸氢钠 作用下， 以 水 、 甲苯 为溶剂， 以18.6 mg的产率得到N-benzylpivalimidoyl cyanide
  参考文献：
  名称：

  Synthesis of Iminonitriles by Oxone/TBAB-Mediated One-Pot Oxidative Three-Component Strecker Reaction

  摘要：

  Oxidative three-component reaction of aldehydes, amines, and TMSCN in a biphasic solvent system (toluene/H2O) containing Oxone, tetra-n-butylammonium bromide (TBAB) and sodium bicarbonate afforded alpha-iminonitriles in good to excellent yields. This oxidative Strecker reaction was applicable to a wide range of aldehydes and amines, aromatic or aliphatic, of different electronic and steric properties. Substituted 1-aza-2-cyano-1,3-dienes were also accessible using alpha,beta-unsaturated aldehydes as inputs.

  DOI：

  10.1055/s-0032-1316908
• 作为产物：
  描述：

  特戊醛 以 甲苯 为溶剂， 反应 0.08h， 生成 N-benzyl 2-amino-3,3-dimethyl butyronitrile
  参考文献：
  名称：

  Synthesis of Iminonitriles by Oxone/TBAB-Mediated One-Pot Oxidative Three-Component Strecker Reaction

  摘要：

  Oxidative three-component reaction of aldehydes, amines, and TMSCN in a biphasic solvent system (toluene/H2O) containing Oxone, tetra-n-butylammonium bromide (TBAB) and sodium bicarbonate afforded alpha-iminonitriles in good to excellent yields. This oxidative Strecker reaction was applicable to a wide range of aldehydes and amines, aromatic or aliphatic, of different electronic and steric properties. Substituted 1-aza-2-cyano-1,3-dienes were also accessible using alpha,beta-unsaturated aldehydes as inputs.

  DOI：

  10.1055/s-0032-1316908

文献信息

• Solvent-Free Synthesis of Racemic α-Aminonitriles
  作者：Carmen Nájera、Alejandro Baeza、José Sansano

  DOI：10.1055/s-2007-965974

  日期：2007.4

  A very simple one-step, environmentally friendly procedure for the synthesis of α-aminonitriles from aldehydes and ketones, using trimethylsilyl cyanide in the absence of solvent, is reported. The active catalyst of this three-component (Strecker) reaction was the amine employed in the transformation. In general, aldehydes react more rapidly than ketones and give almost quantitative yields of the corresponding α-aminonitriles in less than fifteen minutes. However, only cyclic ketones afford the corresponding α-aminonitriles in excellent chemical yields under these conditions.

  报道了一种非常简单的单步环境友好型方法，通过在无溶剂条件下使用三甲基硅烷腈，从醛和酮合成α-氨基腈。该三组分（Strecker）反应的活性催化剂是用于转化反应的胺。通常情况下，醛比酮反应更快，在不到十五分钟内即可几乎定量地生成相应的α-氨基腈。然而，在这些条件下，只有环状酮能以优异的化学产率生成相应的α-氨基腈。
• Catalyst-Free Strecker Reaction in Water: A Simple and Efficient Protocol Using Acetone Cyanohydrin as Cyanide Source
  作者：Paola Galletti、Matteo Pori、Daria Giacomini

  DOI：10.1002/ejoc.201100089

  日期：2011.7

  nitriles through a one-pot, three-component Strecker reaction of a carbonyl compound, amine, and acetone cyanohydrin in water has been developed. Reactions proceed very efficiently without any catalyst at room temperature with high chemoselectivity and give, in some cases, the expected α-amino nitrile pure after direct separation from water. The protocol is particularly efficient for both aliphatic and

  开发了一种简单、方便、实用的方法，通过羰基化合物、胺和丙酮氰醇在水中的一锅三组分 Strecker 反应合成 α-氨基腈。反应在室温下在没有任何催化剂的情况下非常有效地进行，具有高化学选择性，在某些情况下，直接与水分离后得到预期的纯α-氨基腈。该方案对于脂肪族和芳香族醛以及环酮以及伯胺和仲胺都特别有效。报道了 Strecker 反应对 1,2-二胺获得 1,2-二氨基腈和环状仲胺的不寻常应用。
• Reversal of Enantioselectivity by Catalyst Protonation: Asymmetric ­Hydrocyanation of Imines with Oxazaborolidines
  作者：Albrecht Berkessel、Santanu Mukherjee、Johann Lex

  DOI：10.1055/s-2005-922757

  日期：——

  A new application of chiral oxazaborolidines in asymmetric transformation, namely the hydrocyanation of imines, is described. The effect of protonation of these catalysts on the reactivity and enantioselectivity of hydrocyanations is studied. Significant increase in reaction rate is observed upon protonation of the catalysts, along with the reversal of the sense of stereoinduction.

  本文描述了一种手性氧杂硼烷在不对称转化中的新应用，即亚胺的氰化反应。研究了这些催化剂的质子化对氰化反应的反应性和对映选择性的影响。催化剂质子化后，反应速率显著提高，并且立体诱导的方向发生了反转。
• Hassan, Nasser A.; Bayer, Erwin; Jochims, Johannes C., Journal of the Chemical Society. Perkin transactions I, 1998, # 22, p. 3747 - 3757
  作者：Hassan, Nasser A.、Bayer, Erwin、Jochims, Johannes C.

  DOI：——

  日期：——
• Asymmetric addition of trimethylsilylcyanide to N-benzylimines catalyzed by recyclable chiral dimeric V(V) salen complex
  作者：Noor-ul H. Khan、S. Saravanan、Rukhsana I. Kureshy、Sayed H.R. Abdi、Arghya Sadhukhan、Hari C. Bajaj

  DOI：10.1016/j.jorganchem.2010.01.018

  日期：2010.4

  Chiral dimeric vanadium (V) salen complex (10 mol%) derived from 5,5-Methylene di-[(S,S)-N-(3-tert-butyl salicylidine)-N'-(3',5'-di-tert-butyl salicylidene)]-1,2-cyclohexanediamine] with vanadyl suphate followed by auto oxidation was used as efficient catalyst for enantioselective Strecker reaction of N-benzylimines with TMSCN at -30 degrees C. Excellent yield (92%) of alpha-aminonitrile and high chiral induction was achieved (ee up to 94%) in case of 2-methoxy substituted N-benzylimines in 10 h. The catalytic system worked well up to four cycles with retention of enantioselectivity. (C) 2010 Published by Elsevier B. V.