(3aS,8aR)-3-[(1R,5R)-3,4-dimethyl-2-oxo-5-propylcyclopent-3-enecarbonyl]-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one | 1252612-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3aS,8aR)-3-[(1R,5R)-3,4-dimethyl-2-oxo-5-propylcyclopent-3-enecarbonyl]-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one
• 英文别名: (3aR,8bS)-1-[(1R,5R)-3,4-dimethyl-2-oxo-5-propylcyclopent-3-ene-1-carbonyl]-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-2-one
• CAS: 1252612-40-0
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: PMLNAZGNXLKCCH-HPBDAGMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(3aS,8aR)-3-[(1S,5S)-3,4-dimethyl-2-oxo-5-propylcyclopent-3-enecarbonyl]-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-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