(S)-(-)-2-methyl-4-phenyl-3-piperidinobutan-2-ol

• 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)-(-)-2-methyl-4-phenyl-3-piperidinobutan-2-ol
• 英文别名: (S)-2-methyl-4-phenyl-3-(piperidin-1-yl)butan-2-ol；(3S)-2-methyl-4-phenyl-3-piperidin-1-ylbutan-2-ol
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: WYPRDSFKEXRGKS-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  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

文献信息

• Catalytic enantioselective arylation of aldehydes: boronic acids as a suitable source of transferable aryl groups
  作者：Antonio L. Braga、Diogo S. Lüdtke、Fabrício Vargas、Marcio W. Paixão

  DOI：10.1039/b501485a

  日期：——

  The catalytic enantioselective arylation of several aldehydes using boronic acids as the source of transferable aryl groups is described; the reaction is found to proceed in excellent yields and high enantioselectivities (up to 97% ee) in the presence of a chiral amino alcohol.

  描述了使用硼酸作为可转移芳基的来源的几种醛的催化对映选择性芳基化；在手性氨基醇的存在下，发现该反应以优异的产率和高的对映选择性（高达97％ee）进行。
• A convenient synthesis of piperidine-based β-amino alcohols from l-Phe and highly enantioselective addition of diethyl zinc to aldehydes
  作者：Chao-shan Da、Zhi-jian Han、Ming Ni、Fan Yang、Da-xue Liu、Yi-feng Zhou、Rui Wang

  DOI：10.1016/s0957-4166(03)00122-8

  日期：2003.3

  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.