cis-2-Acetyl-3-oxobicyclo<3.3.0>octane | 136202-46-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2-Acetyl-3-oxobicyclo<3.3.0>octane
• CAS: 136202-46-5
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: VZSDHXNFHGJMDX-NHLQPFIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  methyl (2E,7E)-9-oxo-2,7-decadienoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 生成 cis-2-Acetyl-3-oxobicyclo<3.3.0>octane 、 trans-Methyl 2-<2-(2-oxopropyl)cyclopentyl>ethanoate
  参考文献：
  名称：

  Enholm, Eric J.; Kinter, Kevin S., Journal of the American Chemical Society, 1991, vol. 113, # 20, p. 7784 - 7785

  摘要：

  DOI：

文献信息

• Cyclization Reactions of Allylic O-Stannyl Ketyls
  作者：Eric J. Enholm、Kevin S. Kinter

  DOI：10.1021/jo00120a031

  日期：1995.7

  This is a summary of an investigation of the tributyltin hydride-induced cyclization reactions of unsaturated ketones with electronically deficient olefins. This reaction was initiated by an O-stannyl ketyl formed by the addition of a tributyltin radical to a carbonyl, which has both anionic and radical character. The intramolecular coupling produced functionalized cyclopentanes, bearing two synthetically useful carbon appendages. An activating or electron-withdrawing function on the alkene was essential to the cyclization. A dilution study revealed that excellent anti stereoselectivities (>50:1) could be achieved, and this was attributed to a reversible cyclization. Another goal of this study was to separate the radical reactivity from the anionic reactivity of the O-stannyl ketyl by the participation of labile functional groups and external electrophiles. The presence of minor products and enolate-trapping studies demonstrated that the anionic character of the ketyl could be utilized in the form of a tin enolate. This work represents the first free radical- and reagent-based approach to the study of the intramolecular hydrodimerization of activated alkenes.