(S)-3-Methyl-2-((S)-2-phenyl-piperidin-1-yl)-butyric acid methyl ester | 156271-17-9

• 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)-3-Methyl-2-((S)-2-phenyl-piperidin-1-yl)-butyric acid methyl ester
• 英文别名: methyl (2S)-3-methyl-2-[(2S)-2-phenylpiperidin-1-yl]butanoate
• CAS: 156271-17-9
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: IBVKKGMMOOOPRN-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-Methyl-2-((S)-2-phenyl-piperidin-1-yl)-butyric acid methyl ester 在 potassium tert-butylate 作用下， 以 乙醚 、 水 为溶剂， 以55%的产率得到(2S)-2-苯基哌啶
  参考文献：
  名称：

  Reductive amination of 1,4- and 1,5-dicarbonyl compounds with (S)-valine methyl ester. Synthesis of (S)-2-phenylpyrrolidine and (S)-2-phenylpiperidine

  摘要：

  The reductive amination of 4-phenyl-4-oxobutanal and 5-phenyl-5-oxoprentanal with (S)-valine methyl ester and sodium cyanoborohydride afforded the N-substituted (S)-2-phenylpyrrolidine (88% d.e.) and (S)-2-phenylpiperidine (96% d.e.), from which the levorotatory N-H cyclic amines were obtained. On the other hand, the analogous reductive amination of simple ketones, 2,5 hexanedione, and 2,6-heptanedione was poorly selective.

  DOI：

  10.1016/s0040-4039(00)77030-4
• 作为产物：
  描述：

  5-oxo-5-phenylpentanal 、 L-缬氨酸甲酯盐酸盐 在 氢氧化钾 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (S)-3-Methyl-2-((S)-2-phenyl-piperidin-1-yl)-butyric acid methyl ester 、 (S)-3-Methyl-2-(6-phenyl-3,4-dihydro-2H-pyridin-1-yl)-butyric acid methyl ester
  参考文献：
  名称：

  Reductive amination of 1,4- and 1,5-dicarbonyl compounds with (S)-valine methyl ester. Synthesis of (S)-2-phenylpyrrolidine and (S)-2-phenylpiperidine

  摘要：

  The reductive amination of 4-phenyl-4-oxobutanal and 5-phenyl-5-oxoprentanal with (S)-valine methyl ester and sodium cyanoborohydride afforded the N-substituted (S)-2-phenylpyrrolidine (88% d.e.) and (S)-2-phenylpiperidine (96% d.e.), from which the levorotatory N-H cyclic amines were obtained. On the other hand, the analogous reductive amination of simple ketones, 2,5 hexanedione, and 2,6-heptanedione was poorly selective.

  DOI：

  10.1016/s0040-4039(00)77030-4