4-oxo-5,5,6,6,7,7-hexamethyl-1-oxaspiro[2.4]heptane | 180516-50-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-oxo-5,5,6,6,7,7-hexamethyl-1-oxaspiro[2.4]heptane
• 英文别名: 4,4,5,5,6,6-Hexamethyl-1-oxaspiro[2.4]heptan-7-one
• CAS: 180516-50-1
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: LOYLSNYKYAQISB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-oxo-5,5,6,6,7,7-hexamethyl-1-oxaspiro[2.4]heptane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2,3,3,4,4,5,5-heptamethyl-1,2-cyclopentanediol
  参考文献：
  名称：

  Ozonolysis of Highly Methylated 1,2-Bis(methylene)cycloalkanes. Influence of the Methyl Substituents on the Course of the Reaction

  摘要：

  In the ozonolyses of highly methylated 3,3,4,4,5,5-hexamethyl-1,2-bis(methylene)cyclopentane (1a) and 3,3,6,6-tetramethyl-1,2-bis(methylene)cyclohexane (1b), the epoxidation competed with the cleavage of the C-C double bond, whereas only the latter process was observed in the case of the nonmethylated 1,2-bis(methylene)cycloalkanes 1c,d. Competition experiments revealed that the reactivity of the highly methylated 1,2-bis(methylene)cycloalkanes 1a,b is significantly smaller than that of the nonmethylated ones (1c,d), suggesting that the formation of the primary ozonides 2c,d occurs by a concerted 1,3-dipolar cycloaddition process.

  DOI：

  10.1021/jo960397i
• 作为产物：
  描述：

  1,1,2,2,3,3-hexamethyl-4,5-bis(methylene)cyclopentane 在 potassium sulfate 、 potassium hydrogensulfate 、 oxone 、 18-冠醚-6 、 碳酸氢钠 、 臭氧 作用下， 以 乙醚 、 水 、 丙酮 、 苯 为溶剂， 反应 4.0h， 生成 4-oxo-5,5,6,6,7,7-hexamethyl-1-oxaspiro[2.4]heptane
  参考文献：
  名称：

  Ozonolysis of Highly Methylated 1,2-Bis(methylene)cycloalkanes. Influence of the Methyl Substituents on the Course of the Reaction

  摘要：

  In the ozonolyses of highly methylated 3,3,4,4,5,5-hexamethyl-1,2-bis(methylene)cyclopentane (1a) and 3,3,6,6-tetramethyl-1,2-bis(methylene)cyclohexane (1b), the epoxidation competed with the cleavage of the C-C double bond, whereas only the latter process was observed in the case of the nonmethylated 1,2-bis(methylene)cycloalkanes 1c,d. Competition experiments revealed that the reactivity of the highly methylated 1,2-bis(methylene)cycloalkanes 1a,b is significantly smaller than that of the nonmethylated ones (1c,d), suggesting that the formation of the primary ozonides 2c,d occurs by a concerted 1,3-dipolar cycloaddition process.

  DOI：

  10.1021/jo960397i