4-methylene-5,5,6,6,7,7-hexamethyl-1-oxaspiro[2.4]heptane | 180516-51-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-methylene-5,5,6,6,7,7-hexamethyl-1-oxaspiro[2.4]heptane
• 英文别名: 4,4,5,5,6,6-Hexamethyl-7-methylidene-1-oxaspiro[2.4]heptane
• CAS: 180516-51-2
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: RVZCIZZECJHRPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methylene-5,5,6,6,7,7-hexamethyl-1-oxaspiro[2.4]heptane 在 臭氧 作用下， 以 乙醚 为溶剂， 以70%的产率得到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
• 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 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 4.0h， 以60%的产率得到4-methylene-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

文献信息

• Ozonolysis of Highly Methylated 1,2-Bis(methylene)cycloalkanes. Influence of the Methyl Substituents on the Course of the Reaction
  作者：Hideyuki Yamakoshi、Shin-ichi Kawamura、Masatomo Nojima、Herbert Mayr、Janusz Baran

  DOI：10.1021/jo960397i

  日期：1996.1.1

  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.