1-<2-(2-Oxo-2-phenylethyl)-1-pyrrolidinyl>-2,2-dimethylpropanon | 134786-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-<2-(2-Oxo-2-phenylethyl)-1-pyrrolidinyl>-2,2-dimethylpropanon
• 英文别名: 2,2-dimethyl-1-(2-phenacylpyrrolidin-1-yl)propan-1-one
• CAS: 134786-87-1
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: SDCCSRUQSMCZDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-<2-(2-Oxo-2-phenylethyl)-1-pyrrolidinyl>-2,2-dimethylpropanon 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 1-<(R,S)-2-((S,R)-2-Hydroxy-2-phenylethyl)-1-pyrrolidinyl>-2,2-dimethylpropanon 、 1-<(R,S)-2-((R,S)-2-Hydroxy-2-phenylethyl)-1-pyrrolidinyl>-2,2-dimethylpropanon
  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：

  N-pivaloyl-L-proline 在 甲醇 、 sodium methylate 、 四氯化钛 作用下， 生成 1-<2-(2-Oxo-2-phenylethyl)-1-pyrrolidinyl>-2,2-dimethylpropanon
  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