3-ethyl-5-(4-tert-butylphenyl)-1,2,4-trioxolane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-ethyl-5-(4-tert-butylphenyl)-1,2,4-trioxolane
• 英文别名: 3-(4-Tert-butylphenyl)-5-ethyl-1,2,4-trioxolane
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: XPMABXUPGUTYDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  正-3-己烯 、 对叔丁基苯甲醛 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 3-ethyl-5-(4-tert-butylphenyl)-1,2,4-trioxolane
  参考文献：
  名称：

  Electronic effects in the reaction of propionaldehyde oxide with substituted benzaldehydes

  摘要：

  The relative rates of reaction of propionaldehyde oxide with para-substituted benzaldehydes have been measured and treated with the Hammett equation. The Hammett plot indicates that electron-withdrawing substituents in the benzaldehyde increase the reaction rate and give rho = +0.25. Electron-donating substituents in the benzaldehyde also increase the rate (rho = -0.85). The results are interpreted as indicating the presence of two related reaction pathways for ozonide formation. The cis/trans ratios of the ozonides produced in these reactions have been determined and also plotted against the Hammett sigma constants. This plot indicates that electron-withdrawing substituents in the benzaldehyde increase the amount of cis ozonide formed in the reaction with propionaldehyde oxide. The results are interpreted in terms of current views of the mechanism of ozonolysis.

  DOI：

  10.1021/jo00021a030

文献信息

• Electronic effects in the reaction of propionaldehyde oxide with substituted benzaldehydes
  作者：Robert W. Murray、Michael M. Morgan

  DOI：10.1021/jo00021a030

  日期：1991.10

  The relative rates of reaction of propionaldehyde oxide with para-substituted benzaldehydes have been measured and treated with the Hammett equation. The Hammett plot indicates that electron-withdrawing substituents in the benzaldehyde increase the reaction rate and give rho = +0.25. Electron-donating substituents in the benzaldehyde also increase the rate (rho = -0.85). The results are interpreted as indicating the presence of two related reaction pathways for ozonide formation. The cis/trans ratios of the ozonides produced in these reactions have been determined and also plotted against the Hammett sigma constants. This plot indicates that electron-withdrawing substituents in the benzaldehyde increase the amount of cis ozonide formed in the reaction with propionaldehyde oxide. The results are interpreted in terms of current views of the mechanism of ozonolysis.