(1S,6S,8R)-2,7-Dioxo-11-oxa-tricyclo[6.2.1.1^3,6]dodec-9-ene-9,10-dicarboxylic acid dimethyl ester | 109636-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,6S,8R)-2,7-Dioxo-11-oxa-tricyclo[6.2.1.1^3,6]dodec-9-ene-9,10-dicarboxylic acid dimethyl ester
• CAS: 109636-11-5
• 化学式: C₁₅H₁₆O₇
• 分子量: 308.288
• InChiKey: QVBBNJJOLCQZFN-HUBGNOAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.04
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  95.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2,3-dicarbomethoxy-syn-sesquinorborna-2,4a-diene 在 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以30%的产率得到(1S,6S,8R)-2,7-Dioxo-11-oxa-tricyclo[6.2.1.1^3,6]dodec-9-ene-9,10-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Spontaneous oxygenation of cyclic olefins. Effects of strain

  摘要：

  Reactivity of strained olefins 1-3, 41, and 44 toward spontaneous oxygenation has been evaluated. Angle-strained olefins 1, 32, and 35 react spontaneously with ground-state triplet oxygen, at room temperature, to yield quantitatively, not copolymers or hydroperoxides, but epoxides and diketones in approximately a 2:1 ratio. The autoxidation of 1 is carried out with various solvents, inhibitors, initiators, and in the presence of 2 and 1,2-dimethylcyclohexene to determine the mechanistic details. Compared with 1, autoxidation of 2 and 3 follows a different route yielding mainly hydroperoxides along with other products. The mechanism of the spontaneous autoxidation is discussed in light of these results.

  DOI：

  10.1021/jo00021a016