Ethylene ketal of methyl 7-oxo-1-cyclooctenecarboxylate | 90743-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethylene ketal of methyl 7-oxo-1-cyclooctenecarboxylate
• CAS: 90743-34-3
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: KIPKOACKKFZDKN-UHFFFAOYSA-N

物化性质

• 沸点：
  322.9±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Ethylene ketal of methyl 7-oxo-1-cyclooctenecarboxylate 在 三溴化磷 、 二异丁基氢化铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 (E)-7-Bromomethyl-1,4-dioxa-spiro[4.7]dodec-7-ene
  参考文献：
  名称：

  Medium-Ring Systems. 6.¹ Synthesis and Isomerizations of Medium-Ring 3-Methylenecycloalkanones and 3-Methylcycloalkenones

  摘要：

  A series of 3-methylenecycloalkanones with ring sizes 7-10 has been prepared and subjected to base-catalyzed isomerization. Equilibrium between these exocyclic isomers and the corresponding 3-methyl-2-cycloalkenones and 3-methyl-3-cycloalkenones was reached in the 7- and 8-membered rings. The presence of the beta-methyl shifts these equilibria toward the Delta(2) isomer in each ring relative to the unsubstituted compounds and to compounds containing electron-withdrawing groups at the beta position. In the 9- and 10-membered rings, the Delta(2) isomers were isomerized to the Delta(3) isomers only with difficulty, and the reverse process could not be accomplished under the reaction conditions utilized. The ease of interconversion of the Delta(2) and Delta(3) isomers is directly related to the thermodynamic stability of planar conjugated dienes in medium ring carbocycles.

  DOI：

  10.1021/jo9705374
• 作为产物：
  描述：

  乙二醇 、 Methyl 7-oxocyclooctene-1-carboxylate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以100%的产率得到Ethylene ketal of methyl 7-oxo-1-cyclooctenecarboxylate
  参考文献：
  名称：

  Medium-Ring Systems. 6.¹ Synthesis and Isomerizations of Medium-Ring 3-Methylenecycloalkanones and 3-Methylcycloalkenones

  摘要：

  A series of 3-methylenecycloalkanones with ring sizes 7-10 has been prepared and subjected to base-catalyzed isomerization. Equilibrium between these exocyclic isomers and the corresponding 3-methyl-2-cycloalkenones and 3-methyl-3-cycloalkenones was reached in the 7- and 8-membered rings. The presence of the beta-methyl shifts these equilibria toward the Delta(2) isomer in each ring relative to the unsubstituted compounds and to compounds containing electron-withdrawing groups at the beta position. In the 9- and 10-membered rings, the Delta(2) isomers were isomerized to the Delta(3) isomers only with difficulty, and the reverse process could not be accomplished under the reaction conditions utilized. The ease of interconversion of the Delta(2) and Delta(3) isomers is directly related to the thermodynamic stability of planar conjugated dienes in medium ring carbocycles.

  DOI：

  10.1021/jo9705374