(S)-(-)-3-phenyl-2-piperidinopropionic acid methyl ester | 571970-66-6

• 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: (S)-(-)-3-phenyl-2-piperidinopropionic acid methyl ester
• 英文别名: methyl (2S)-3-phenyl-2-piperidin-1-ylpropanoate
• CAS: 571970-66-6
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: ZHDGIWAWWUNORR-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  溴甲烷 、 (S)-(-)-3-phenyl-2-piperidinopropionic acid methyl ester 在 magnesium 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以97%的产率得到(S)-(-)-2-methyl-4-phenyl-3-piperidinobutan-2-ol
  参考文献：
  名称：

  A convenient synthesis of piperidine-based β-amino alcohols from l-Phe and highly enantioselective addition of diethyl zinc to aldehydes

  摘要：

  beta-Amino alcohols 4a-e were easily prepared from L-phenylalanine. in three simple straightforward steps. The key intermediate compound (S)-3 was achieved in high yield (up to 92%) with glutaraldehyde and NaBH4/H2SO4 in THF at room temperature. These five ligands were applied to catalyze enantioselective addition of diethyl zinc to aldehydes, high asymmetric induction was observed with 4c and 4e, and the ee value was up to 98%. The effect of the substitutes on the nitrogen atom was also observed via comparing piperidine-based amino alcohols with pyrrolidine-based similar ligands. (0 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00122-8
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 、 戊二醛 在 sodium tetrahydroborate 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以92%的产率得到(S)-(-)-3-phenyl-2-piperidinopropionic acid methyl ester
  参考文献：
  名称：

  A convenient synthesis of piperidine-based β-amino alcohols from l-Phe and highly enantioselective addition of diethyl zinc to aldehydes

  摘要：

  beta-Amino alcohols 4a-e were easily prepared from L-phenylalanine. in three simple straightforward steps. The key intermediate compound (S)-3 was achieved in high yield (up to 92%) with glutaraldehyde and NaBH4/H2SO4 in THF at room temperature. These five ligands were applied to catalyze enantioselective addition of diethyl zinc to aldehydes, high asymmetric induction was observed with 4c and 4e, and the ee value was up to 98%. The effect of the substitutes on the nitrogen atom was also observed via comparing piperidine-based amino alcohols with pyrrolidine-based similar ligands. (0 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00122-8