2-methyl-2-((1-phenylethyl)amino)propane-nitrile | 934815-48-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-methyl-2-((1-phenylethyl)amino)propane-nitrile
• 英文别名: 2-methyl-2-[[(1R)-1-phenylethyl]amino]propanenitrile
• CAS: 934815-48-2
• 化学式: C₁₂H₁₆N₂
• 分子量: 188.272
• InChiKey: VJGVMJATGPCNCU-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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-methyl-2-((1-phenylethyl)amino)propane-nitrile 、 2-(溴甲基)苯甲醛 在 (S)-(-)-α-methylbenzylamine hydrochloride 作用下， 以 乙腈 为溶剂， 以12%的产率得到2-((1R)-1-phenylethyl)isoindolin-1-one
  参考文献：
  名称：

  An approach to 2-cyanopyrrolidines bearing a chiral auxiliary

  摘要：

  The reaction of 2-methyl-2-(1-phenylethyl)amino)propanenitrile with different gamma-halocarbonyl compounds is investigated. The influence of different parameters such as the nature of the substrate and solvent, is discussed. The reaction is considered as a convenient route to 2-cyanopyrrolidines in the case of aliphatic gamma-halocarbonyl compounds possessing a reasonably reactive carbonyl group. In many cases, the products can be obtained as single enantiomers. It is shown that cyclopropyl ketones can also react with 2-methyl-2-((1-phenylethyl)amino)propanenitrile to give 2-cyanopyrrolidines. A mechanistic scheme is proposed in order to explain the experimental facts observed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.008
• 作为产物：
  描述：

  三甲基乙腈 、 R(+)-alpha-甲基苄胺 、 丙酮氰醇 在 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 2-methyl-2-((1-phenylethyl)amino)propane-nitrile 、 (R)-3,3-Dimethyl-2-((R)-1-phenyl-ethylamino)-butyronitrile 、 (S)-3,3-Dimethyl-2-((R)-1-phenyl-ethylamino)-butyronitrile
  参考文献：
  名称：

  One-pot synthesis of α-aminonitriles from alkyl and aryl cyanides: a Strecker reaction via aldimine alanes

  摘要：

  A one-pot Strecker reaction using various alkyl, arylalkyl and arylnitriles is developed. Aldimine alanes were generated in situ from nitriles by the addition of diisobutylaluminium hydride, and were converted into the corresponding imines on reaction with (S)-(-)-1-phenylethylamine. Nucleophilic addition to the imines in the presence of catalytic triethylamine, using acetone cyanohydrin as a cyanide source, provided alpha-aminonitriles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.004