(S,S)-2-[(1-phenylethyl)amino]-2-cyclohexylethanenitrile | 617710-48-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S,S)-2-[(1-phenylethyl)amino]-2-cyclohexylethanenitrile
• 英文别名: (2S)-2-cyclohexyl-2-[[(1S)-1-phenylethyl]amino]acetonitrile
• CAS: 617710-48-2
• 化学式: C₁₆H₂₂N₂
• 分子量: 242.364
• InChiKey: DIZGFDOJOCHKJD-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 环己甲腈 、 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 、 (2R)-2-cyclohexyl-2-[[(1S)-1-phenylethyl]amino]acetonitrile 、 (S,S)-2-[(1-phenylethyl)amino]-2-cyclohexylethanenitrile
  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

文献信息

• One-pot synthesis of α-aminonitriles from alkyl and aryl cyanides: a Strecker reaction via aldimine alanes
  作者：Szabolcs Sipos、István Jablonkai

  DOI：10.1016/j.tetlet.2009.02.004

  日期：2009.4

  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.