(2S)-N-benzyl-N-methylpyrrolidine-2-carboxamide | 1217612-28-6

• 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: (2S)-N-benzyl-N-methylpyrrolidine-2-carboxamide
• CAS: 1217612-28-6
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: GHPBLQMIVDJABJ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-N-benzyl-N-methylpyrrolidine-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-N(H)-2-2-<(N-benzyl-N-methylamino)methyl>pyrrolidine
  参考文献：
  名称：

  A New Chiral Synthesis of Wieland-Miescher Ketone Catalyzed by a Combination of (S)-N-Benzyl-N-(2-pyrrolidinylmethyl)amine Derivative and Brønsted Acid

  摘要：

  New or known N-benzyl-N-(2-pyrrolidinylmethyl)amine derivatives bearing a variety of substituents on the aromatic ring were easily prepared from N-Boc-proline or N-Boc-prolinol. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and Bronsted acid to prepare Wieland-Miescher ketone was examined in detail. During the examination, remarkable substitutional effects on the aromatic ring were observed. Development of a catalytic version of the reaction was successfully achieved by the use of N-[(9-anthracenyl)methyl]-N-(2-pyrrolidinylmethyl)amine in the presence of dichloroacetic acid.

  DOI：

  10.3987/com-08-s(f)86
• 作为产物：
  描述：

  tert-butyl (S)-2-[(benzylmethyl)carbamoyl]pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S)-N-benzyl-N-methylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  A New Chiral Synthesis of Wieland-Miescher Ketone Catalyzed by a Combination of (S)-N-Benzyl-N-(2-pyrrolidinylmethyl)amine Derivative and Brønsted Acid

  摘要：

  New or known N-benzyl-N-(2-pyrrolidinylmethyl)amine derivatives bearing a variety of substituents on the aromatic ring were easily prepared from N-Boc-proline or N-Boc-prolinol. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and Bronsted acid to prepare Wieland-Miescher ketone was examined in detail. During the examination, remarkable substitutional effects on the aromatic ring were observed. Development of a catalytic version of the reaction was successfully achieved by the use of N-[(9-anthracenyl)methyl]-N-(2-pyrrolidinylmethyl)amine in the presence of dichloroacetic acid.

  DOI：

  10.3987/com-08-s(f)86