(S)-3-[(4S,5R)-1-benzyl-6-oxo-4-phenyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-5-carbonyl]-4-phenyloxazolidin-2-one | 1252612-52-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (S)-3-[(4S,5R)-1-benzyl-6-oxo-4-phenyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-5-carbonyl]-4-phenyloxazolidin-2-one
• 英文别名: (4S)-3-[(4S,5R)-1-benzyl-6-oxo-4-phenyl-4,5-dihydrocyclopenta[b]pyrrole-5-carbonyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 1252612-52-4
• 化学式: C₃₀H₂₄N₂O₄
• 分子量: 476.532
• InChiKey: IWRVPXMPPKSQGA-UODIDJSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S,Z)-1-(1-benzyl-1H-pyrrol-2-yl)-2-benzylidene-3-(2-oxo-4-phenyloxazolidin-3-yl)propane-1,3-dione 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以51%的产率得到(S)-3-[(4S,5R)-1-benzyl-6-oxo-4-phenyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-5-carbonyl]-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric Synthesis of Five-Membered Carbocycles

  摘要：

  Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille-Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.

  DOI：

  10.1021/jo100736p