(3aR,6aS)-4-benzyl-2-phenyl-6,6a-dihydro-3aH-pyrrolo[2,3-d]oxazol-5(4H)-one | 1017553-59-1

• 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: (3aR,6aS)-4-benzyl-2-phenyl-6,6a-dihydro-3aH-pyrrolo[2,3-d]oxazol-5(4H)-one
• 英文别名: (3aR,6aS)-4-benzyl-2-phenyl-6,6a-dihydro-3aH-pyrrolo[2,3-d][1,3]oxazol-5-one
• CAS: 1017553-59-1
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: BXBYASKJKSHVDG-DOTOQJQBSA-N

物化性质

• 熔点：
  96-98 °C
• 沸点：
  522.6±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4S)-1-benzyl-4,5-dihydroxypyrrolidin-2-one 、 苯甲腈 在 三氟化硼乙醚 作用下， 反应 16.0h， 以86%的产率得到(3aR,6aS)-4-benzyl-2-phenyl-6,6a-dihydro-3aH-pyrrolo[2,3-d]oxazol-5(4H)-one
  参考文献：
  名称：

  Diastereoselective Ritter Reactions of Chiral Cyclic N-Acyliminium Ions:  Synthesis of Pyrido- and Pyrrolo[2,3-d]oxazoles and 4-Hydroxy-5-N-acylaminopyrrolidines and 5-Hydroxy-6-N-acylaminopiperidines

  摘要：

  Pyrido- and pyrrolo[2,3-d]oxazoles can be conveniently prepared in high yield from the Ritter reaction of nitriles and in situ generated chiral cyclic N-acyliminium ions. cis-4-Hydroxy-5-acylaminopyrrolidines and cis-5-hydroxy-6-acylaminopiperidines can be readily obtained by acid hydrolysis of these bicyclic heterocyclic compounds, respectively.

  DOI：

  10.1021/jo800007g

文献信息

• Diastereoselective Ritter Reactions of Chiral Cyclic <i>N</i>-Acyliminium Ions:  Synthesis of Pyrido- and Pyrrolo[2,3-<i>d</i>]oxazoles and 4-Hydroxy-5-<i>N</i>-acylaminopyrrolidines and 5-Hydroxy-6-<i>N</i>-acylaminopiperidines
  作者：Ian R. Morgan、Arife Yazici、Stephen G. Pyne、Brian W. Skelton

  DOI：10.1021/jo800007g

  日期：2008.4.1

  Pyrido- and pyrrolo[2,3-d]oxazoles can be conveniently prepared in high yield from the Ritter reaction of nitriles and in situ generated chiral cyclic N-acyliminium ions. cis-4-Hydroxy-5-acylaminopyrrolidines and cis-5-hydroxy-6-acylaminopiperidines can be readily obtained by acid hydrolysis of these bicyclic heterocyclic compounds, respectively.