<(S)-1-Benzyl-2-<(S)-2-((R)-2-hydroxy-2-phenylethyl)-pyrrolidino>-2-oxoethyl>-2,2-dimethylpropionat | 134786-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: <(S)-1-Benzyl-2-<(S)-2-((R)-2-hydroxy-2-phenylethyl)-pyrrolidino>-2-oxoethyl>-2,2-dimethylpropionat
• 英文别名: [(2S)-1-[(2S)-2-[(2R)-2-hydroxy-2-phenylethyl]pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl] 2,2-dimethylpropanoate
• CAS: 134786-81-5
• 化学式: C₂₆H₃₃NO₄
• 分子量: 423.552
• InChiKey: KUPFKPPGCCNSNY-ZRBLBEILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  <(S)-1-Benzyl-2-<(S)-2-((R)-2-hydroxy-2-phenylethyl)-pyrrolidino>-2-oxoethyl>-2,2-dimethylpropionat 在 四丁基氢氧化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以54%的产率得到(R)-1-Phenyl-2-<(S)-2-pyrrolidinyl>ethanol
  参考文献：
  名称：

  Chelat- und nicht-chelat-kontrollierte reduktionen von β-amido-ketonen: Synthese nicht-racemischer 1,3-aminoalkohole mit pyrrolidinstruktur

  摘要：

  The reduction of the amidoketones (R)-1 and (S)-2 has been achieved in a stereocontrolled manner giving either the product with like- or unlike configuration depending upon the reducing agent employed. Thus with Li(O(t)Bu)3AlH the amidoalcohols (R,R)-3 and (S,S)-5 were the major diastereomers formed whereas with K((s)Bu)3BH (R,S)-4 and (S,R)-6 dominated. Stereoselectivities up to 98/2 were observed. As a mechanistic rationale for the change of direction in the asymmetric induction a chelate- and non-chelate-model have been envoked.By including (rac)-9 in this study having a non chiral acyl group it was found that the chiral auxiliary in (R)-1/(S)-2 is essential for a high asymmetric induction under chelate- but not under non-chelate-control.Hydrolysis of the amidoalcohols provided the corresponding 1,3-aminoalcohols (R,R)-12, (S,S)-12, (R,S)-13 and (S,R)-13. The configuration of these compounds has been assigned by means of H-1 NMR spectroscopy.

  DOI：

  10.1016/s0040-4020(01)96102-2
• 作为产物：
  描述：

  <(S)-1-Benzyl-2-<(S)-2-(2-oxo-2-phenylethyl)-pyrrolidino>-2-oxoethyl>-2,2-dimethylpropionat 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以47.3%的产率得到<(S)-1-Benzyl-2-<(S)-2-((S)-2-hydroxy-2-phenylethyl)-pyrrolidino>-2-oxoethyl>-2,2-dimethylpropionat
  参考文献：
  名称：

  Chelat- und nicht-chelat-kontrollierte reduktionen von β-amido-ketonen: Synthese nicht-racemischer 1,3-aminoalkohole mit pyrrolidinstruktur

  摘要：

  The reduction of the amidoketones (R)-1 and (S)-2 has been achieved in a stereocontrolled manner giving either the product with like- or unlike configuration depending upon the reducing agent employed. Thus with Li(O(t)Bu)3AlH the amidoalcohols (R,R)-3 and (S,S)-5 were the major diastereomers formed whereas with K((s)Bu)3BH (R,S)-4 and (S,R)-6 dominated. Stereoselectivities up to 98/2 were observed. As a mechanistic rationale for the change of direction in the asymmetric induction a chelate- and non-chelate-model have been envoked.By including (rac)-9 in this study having a non chiral acyl group it was found that the chiral auxiliary in (R)-1/(S)-2 is essential for a high asymmetric induction under chelate- but not under non-chelate-control.Hydrolysis of the amidoalcohols provided the corresponding 1,3-aminoalcohols (R,R)-12, (S,S)-12, (R,S)-13 and (S,R)-13. The configuration of these compounds has been assigned by means of H-1 NMR spectroscopy.

  DOI：

  10.1016/s0040-4020(01)96102-2