(4R)-1-[(1S)-2-hydroxy-1-phenylethyl]-4-phenylpyrrolidin-2-one | 145549-06-0

• 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: (4R)-1-[(1S)-2-hydroxy-1-phenylethyl]-4-phenylpyrrolidin-2-one
• CAS: 145549-06-0
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: XEOWHUIZOVWAEM-DLBZAZTESA-N

物化性质

• 沸点：
  499.6±45.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-1-[(1S)-2-hydroxy-1-phenylethyl]-4-phenylpyrrolidin-2-one 在 氨 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.17h， 以99%的产率得到(R)-4-苯基吡咯烷-2-酮
  参考文献：
  名称：

  The synthesis of aracemic 4-substituted pyrrolidinones and 3-substituted pyrrolidines. An asymmetric synthesis of (-)-rolipram

  摘要：

  Conjugate additions of RCuCNLi to the chiral alpha,beta-unsaturated lactam 4 gives almost exclusive exo addition-a reversal in stereochemistry when cuprates were added to chiral lactam 1. The lactams 5 were transformed into 4-substituted pyrrolidinones 8 via a three-step sequence which involved decarbalkoxylation, silane reduction and metal-ammonia benzylamine cleavage. The chemical yields as well as the enantiomeric purity were very high for this process. As an example of the usefulness of this scheme, the antidepressant (-)-Rolipram was prepared in good overall yield. Furthermore, the bicyclic lactams 6 were readily transformed, using alane as the reducing agent, to 3-substituted pyrrolidines 11. Absolute configurations of 8 and 11 were confirmed by comparison with literature assignments which also gave strong support to the facial addition of the cuprates to 4.

  DOI：

  10.1021/jo00053a012
• 作为产物：
  描述：

  (3S,7R,7aR)-3,7-diphenyl-3,6,7,7a-tetrahydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one 在 三乙基硅烷 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到(4R)-1-[(1S)-2-hydroxy-1-phenylethyl]-4-phenylpyrrolidin-2-one
  参考文献：
  名称：

  The synthesis of aracemic 4-substituted pyrrolidinones and 3-substituted pyrrolidines. An asymmetric synthesis of (-)-rolipram

  摘要：

  Conjugate additions of RCuCNLi to the chiral alpha,beta-unsaturated lactam 4 gives almost exclusive exo addition-a reversal in stereochemistry when cuprates were added to chiral lactam 1. The lactams 5 were transformed into 4-substituted pyrrolidinones 8 via a three-step sequence which involved decarbalkoxylation, silane reduction and metal-ammonia benzylamine cleavage. The chemical yields as well as the enantiomeric purity were very high for this process. As an example of the usefulness of this scheme, the antidepressant (-)-Rolipram was prepared in good overall yield. Furthermore, the bicyclic lactams 6 were readily transformed, using alane as the reducing agent, to 3-substituted pyrrolidines 11. Absolute configurations of 8 and 11 were confirmed by comparison with literature assignments which also gave strong support to the facial addition of the cuprates to 4.

  DOI：

  10.1021/jo00053a012

文献信息

• The synthesis of aracemic 4-substituted pyrrolidinones and 3-substituted pyrrolidines. An asymmetric synthesis of (-)-rolipram
  作者：A. I. Meyers、Lawrence Snyder

  DOI：10.1021/jo00053a012

  日期：1993.1

  Conjugate additions of RCuCNLi to the chiral alpha,beta-unsaturated lactam 4 gives almost exclusive exo addition-a reversal in stereochemistry when cuprates were added to chiral lactam 1. The lactams 5 were transformed into 4-substituted pyrrolidinones 8 via a three-step sequence which involved decarbalkoxylation, silane reduction and metal-ammonia benzylamine cleavage. The chemical yields as well as the enantiomeric purity were very high for this process. As an example of the usefulness of this scheme, the antidepressant (-)-Rolipram was prepared in good overall yield. Furthermore, the bicyclic lactams 6 were readily transformed, using alane as the reducing agent, to 3-substituted pyrrolidines 11. Absolute configurations of 8 and 11 were confirmed by comparison with literature assignments which also gave strong support to the facial addition of the cuprates to 4.