(S)-1-benzyloxycarbonyl-N-methyl-N-(2-naphthyl)-2-pyrrolidinecarboxamide | 223769-26-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1-benzyloxycarbonyl-N-methyl-N-(2-naphthyl)-2-pyrrolidinecarboxamide
• 英文别名: benzyl (2S)-2-[methyl(naphthalen-2-yl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 223769-26-4
• 化学式: C₂₄H₂₄N₂O₃
• 分子量: 388.466
• InChiKey: GMCVPXODUWNIBF-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-benzyloxycarbonyl-N-methyl-N-(2-naphthyl)-2-pyrrolidinecarboxamide 在 硼烷四氢呋喃络合物 、 氢溴酸 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-N-methyl-N-(2-naphthyl)-2-pyrrolidinemethanamine
  参考文献：
  名称：

  Enantioselective Synthesis of Binaphthol Derivatives by Oxidative Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine·Copper Complexes

  摘要：

  A highly efficient process of aerobic oxidative coupling of 2-naphthol derivatives catalyzed by 1 mol % of Cu(OH)Cl.TMEDA has been developed, Enantioselective oxidative coupling of naphthols was achieved by the use of 10 mol % of chiral catalysts prepared from proline-derived diamines and cuprous chloride, affording the corresponding binaphthols in good enantioselectivities of up to 78% ee. The ester moiety at the 3-position of the substrate was found to be essential for the good asymmetric induction observed in the present coupling reaction.

  DOI：

  10.1021/jo981808t
• 作为产物：
  描述：

  Z-L-脯氨酸β-萘酰胺 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-1-benzyloxycarbonyl-N-methyl-N-(2-naphthyl)-2-pyrrolidinecarboxamide
  参考文献：
  名称：

  Enantioselective Synthesis of Binaphthol Derivatives by Oxidative Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine·Copper Complexes

  摘要：

  A highly efficient process of aerobic oxidative coupling of 2-naphthol derivatives catalyzed by 1 mol % of Cu(OH)Cl.TMEDA has been developed, Enantioselective oxidative coupling of naphthols was achieved by the use of 10 mol % of chiral catalysts prepared from proline-derived diamines and cuprous chloride, affording the corresponding binaphthols in good enantioselectivities of up to 78% ee. The ester moiety at the 3-position of the substrate was found to be essential for the good asymmetric induction observed in the present coupling reaction.

  DOI：

  10.1021/jo981808t