(2R,3S)-N-(3-dibenzylamino-2-hydroxy-5-methylhexyl)propionamide

• 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: (2R,3S)-N-(3-dibenzylamino-2-hydroxy-5-methylhexyl)propionamide
• 英文别名: N-[(2R,3S)-3-(dibenzylamino)-2-hydroxy-5-methylhexyl]propanamide
• 化学式: C₂₄H₃₄N₂O₂
• 分子量: 382.546
• InChiKey: GYBNNCQBOLYQKU-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  、 丙腈 在 三氟化硼乙醚 作用下， 反应 12.0h， 以60%的产率得到(2R,3S)-N-(3-dibenzylamino-2-hydroxy-5-methylhexyl)propionamide
  参考文献：
  名称：

  Regioselective Ring Opening of Amino Epoxides with Nitriles:  An Easy Synthesis of (2R,3S)- and (2S,3S)-1,3-Diaminoalkan-2-ols with Differently Protected Amine Functions

  摘要：

  Transformation of enantiopure (2R,1'S)- or (2S,1'S)-2-(laminoalkyl)epoxides 1 or 2 into the corresponding (2R,3S)and (2S,3S)-1,3-diaminoalkan-2-ols 3 or 4 is described. The opening of the epoxide ring with different nitriles (Ritter reaction) takes place with total selectivity and in high yields in the presence of BF(3)center dot Et2O. Interestingly, the two amine groups are differently protected. A mechanism to explain this transformation is proposed.

  DOI：

  10.1021/jo051109y

文献信息

• Regioselective Ring Opening of Amino Epoxides with Nitriles:  An Easy Synthesis of (2<i>R</i>,3<i>S</i>)- and (2<i>S</i>,3<i>S</i>)-1,3-Diaminoalkan-2-ols with Differently Protected Amine Functions
  作者：José M. Concellón、José Ramón Suárez、Virginia del Solar

  DOI：10.1021/jo051109y

  日期：2005.9.1

  Transformation of enantiopure (2R,1'S)- or (2S,1'S)-2-(laminoalkyl)epoxides 1 or 2 into the corresponding (2R,3S)and (2S,3S)-1,3-diaminoalkan-2-ols 3 or 4 is described. The opening of the epoxide ring with different nitriles (Ritter reaction) takes place with total selectivity and in high yields in the presence of BF(3)center dot Et2O. Interestingly, the two amine groups are differently protected. A mechanism to explain this transformation is proposed.