(2R,3R)-3-azido-1-benzyl-2-phenyl piperidine | 1448991-01-2

• 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: (2R,3R)-3-azido-1-benzyl-2-phenyl piperidine
• CAS: 1448991-01-2
• 化学式: C₁₈H₂₀N₄
• 分子量: 292.384
• InChiKey: SVUDMNIWBAAHTI-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-azido-1-benzyl-2-phenyl piperidine 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、482.64 kPa 条件下， 反应 65.0h， 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
• 作为产物：
  描述：

  (S)-[(2S)-1-benzylpyrrolidin-2-yl](phenyl)methanol 在 sodium azide 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (2R,3R)-3-azido-1-benzyl-2-phenyl piperidine
  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