N-[(2R,3R)-1-benzyl-2-phenylpiperidin-3-yl]acetamide | 1448991-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-[(2R,3R)-1-benzyl-2-phenylpiperidin-3-yl]acetamide
• CAS: 1448991-07-8
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: JTUWCCIYOUGDLM-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-[(2S)-1-benzylpyrrolidin-2-yl](phenyl)methanol 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 55.0 ℃ 、482.64 kPa 条件下， 反应 72.0h， 生成 N-[(2R,3R)-1-benzyl-2-phenylpiperidin-3-yl]acetamide
  参考文献：
  名称：

  Synthesis of Versatile Bifunctional Derivatives of Chiral Diamines Obtained through Anchimerically Assisted Nucleophilic Substitution Reactions on Diastereomeric Phenylprolinols

  摘要：

  Diastereomeric [(S)-1-benzylpyrrolidin-2-yl]-(R)-[(phenyl)methanamine] and [(S)-1-benzylpyrrolidin-2-yl]-(S)-[(phenyl)methanamine], were synthesized by selective internal backside nucleophilic substitution of the corresponding activated phenylprolinols. X-Ray diffraction structures of crystalline acetamide derivatives confirmed the anticipated stereochemistry for a S(N)ib reaction mechanism. In order to apply this reaction to the synthesis of bifunctional analogs, a series of fragments such as a thiourea moiety and sulfonamide functions were introduced for the functionalization of the primary amino group in the substrate, obtaining more stable and potentially useful derivatives.

  DOI：

  10.3987/com-12-s(n)82

文献信息

• Synthesis of Versatile Bifunctional Derivatives of Chiral Diamines Obtained through Anchimerically Assisted Nucleophilic Substitution Reactions on Diastereomeric Phenylprolinols
  作者：Eusebio Juaristi、Jorge Vargas-Caporali、Carlos Cruz-Hernández

  DOI：10.3987/com-12-s(n)82

  日期：——

  Diastereomeric [(S)-1-benzylpyrrolidin-2-yl]-(R)-[(phenyl)methanamine] and [(S)-1-benzylpyrrolidin-2-yl]-(S)-[(phenyl)methanamine], were synthesized by selective internal backside nucleophilic substitution of the corresponding activated phenylprolinols. X-Ray diffraction structures of crystalline acetamide derivatives confirmed the anticipated stereochemistry for a S(N)ib reaction mechanism. In order to apply this reaction to the synthesis of bifunctional analogs, a series of fragments such as a thiourea moiety and sulfonamide functions were introduced for the functionalization of the primary amino group in the substrate, obtaining more stable and potentially useful derivatives.