(S)-[(S)-1-benzylpyrrolidin-2-yl](phenyl)methanamine | 1448991-03-4

• 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: (S)-[(S)-1-benzylpyrrolidin-2-yl](phenyl)methanamine
• 英文别名: (S)-[(2S)-1-benzylpyrrolidin-2-yl]-phenylmethanamine
• CAS: 1448991-03-4
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: VZMVPHLBJATQKJ-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-[(S)-1-benzylpyrrolidin-2-yl](phenyl)methanamine 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到N-{(S)-[(S)-1-benzylpyrrolidin-2-yl](phenyl)methyl}-4-methylbenzenesulfonamide
  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)-2-((S)-azido(phenyl)methyl)pyrrolidine 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (S)-[(S)-1-benzylpyrrolidin-2-yl](phenyl)methanamine
  参考文献：
  名称：

  New class of bifunctional thioureas from l-proline: highly enantioselective Michael addition of 1,3-dicarbonyls to nitroolefins

  摘要：

  A new class of bifunctional tertiary amine thiourea was synthesized from L-proline. The reported thiourea is amenable to steric and electronic modifications at the stereogenic center bearing a thiourea moiety. Excellent enantioselectivity was obtained in the Michael addition of 2,4-pentanedione to various nitro olefins using the new organocatalyst. The construction of contiguous stereocenters via the Michael reaction of substituted 1,3-dicarbonyls to nitro olefins was also carried out with very good yield, enantioselectivity, and diastereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.02.011

文献信息

• New class of bifunctional thioureas from l-proline: highly enantioselective Michael addition of 1,3-dicarbonyls to nitroolefins
  作者：Poopathy Vinayagam、Manjunatha Vishwanath、Venkitasamy Kesavan

  DOI：10.1016/j.tetasy.2014.02.011

  日期：2014.4

  A new class of bifunctional tertiary amine thiourea was synthesized from L-proline. The reported thiourea is amenable to steric and electronic modifications at the stereogenic center bearing a thiourea moiety. Excellent enantioselectivity was obtained in the Michael addition of 2,4-pentanedione to various nitro olefins using the new organocatalyst. The construction of contiguous stereocenters via the Michael reaction of substituted 1,3-dicarbonyls to nitro olefins was also carried out with very good yield, enantioselectivity, and diastereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.