(3S,7R,7aR)-7-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenyl-3,6,7,7a-tetrahydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one | 145548-98-7

• 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: (3S,7R,7aR)-7-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenyl-3,6,7,7a-tetrahydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one
• CAS: 145548-98-7
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: AALHUBPEBAGZDN-YOSAUDMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,7R,7aR)-7-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenyl-3,6,7,7a-tetrahydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one 在 三乙基硅烷 、 三氟化硼乙醚 、 氨 、 四氯化钛 、 lithium 作用下， 生成 (R)-(-)-咯利普兰
  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：

  4-溴-2-(环戊基氧基)苯甲醚 在 palladium on activated charcoal ammonium formate 作用下， 反应 3.0h， 生成 (3S,7R,7aR)-7-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenyl-3,6,7,7a-tetrahydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-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