5,5,5-trichloro-2,3-epoxy-2,3-dimethylpentane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 5,5,5-trichloro-2,3-epoxy-2,3-dimethylpentane
• 英文别名: 2,2,3-Trimethyl-3-(2,2,2-trichloroethyl)oxirane
• 化学式: C₇H₁₁Cl₃O
• 分子量: 217.523
• InChiKey: UOVPCLZZTMTTGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  trichloroiodomethane 、 2,3-dimethyl-3-<(1-methoxy-1-methylethyl)peroxy>but-1-ene 在 三乙基硼 作用下， 以 苯 为溶剂， 生成 5,5,5-trichloro-2,3-epoxy-2,3-dimethylpentane
  参考文献：
  名称：

  Intramolecular Homolytic Displacements. 25. Efficient Access to Epoxides via Induced Decomposition of Unsaturated Peroxyketals Prepared by Addition of a Hydroperoxide to 2-Methoxypropene

  摘要：

  The synthetic potential of homolytically induced decompositions of peroxyketals possessing a 1-methoxy-1-methylethoxy fragment, as a means of access to epoxides, was demonstrated. The propagation step of this free radical reaction proceeds via (i) the addition of a carbon-centered radical to the double bond followed by an S(H)i reaction on the peroxidic bond with the generation of a 1-methoxy-1-methylethoxy radical, (ii) formation of a methyl radical from the latter by beta-elimination, and (iii) regeneration of the carbon-centered-radical via iodine atom abstraction by the methyl radical from an alkyl iodide. These reactions afforded various functionalized epoxides in good yields.

  DOI：

  10.1021/jo951783n

文献信息

• Intramolecular Homolytic Displacements. 25. Efficient Access to Epoxides via Induced Decomposition of Unsaturated Peroxyketals Prepared by Addition of a Hydroperoxide to 2-Methoxypropene
  作者：Fabienne Ramon、Marie Degueil-Castaing、Bernard Maillard

  DOI：10.1021/jo951783n

  日期：1996.1.1

  The synthetic potential of homolytically induced decompositions of peroxyketals possessing a 1-methoxy-1-methylethoxy fragment, as a means of access to epoxides, was demonstrated. The propagation step of this free radical reaction proceeds via (i) the addition of a carbon-centered radical to the double bond followed by an S(H)i reaction on the peroxidic bond with the generation of a 1-methoxy-1-methylethoxy radical, (ii) formation of a methyl radical from the latter by beta-elimination, and (iii) regeneration of the carbon-centered-radical via iodine atom abstraction by the methyl radical from an alkyl iodide. These reactions afforded various functionalized epoxides in good yields.