ethyl 2,3-epoxy-2-(2-chloroethyl)butanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2,3-epoxy-2-(2-chloroethyl)butanoate
• 英文别名: Ethyl 2-(2-chloroethyl)-3-methyloxirane-2-carboxylate
• 化学式: C₈H₁₃ClO₃
• 分子量: 192.642
• InChiKey: PGRMVJVOOSMHHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 3-hydroperoxy-2-methylenebutanoate 在 N-氯代丁二酰亚胺 、 过氧化乙酸叔丁酯 、 碳酸氢钠 作用下， 以 乙醚 、 苯 为溶剂， 反应 12.0h， 生成 ethyl 2,3-epoxy-2-(2-chloroethyl)butanoate
  参考文献：
  名称：

  Intramolecular Homolytic Displacements. 24. Simple Access to Glycidic Esters via Induced Decomposition of Peroxyketals Derived from Ethyl 2-(1-Hydroperoxyethyl)propenoate

  摘要：

  The synthetic potential of the homolytic-induced decomposition of peroxyketals peroxyketals derived from ethyl 2-(1-hydroperoxyethyl)propenoate to access glycidic esters was demonstrated. The propagation step of this free radical chain reaction proceeds via the addition of an alkyl radical to the double bond followed by S(H)i on the peroxidic bond with the production of an oxy radical, regenerating rapidly by beta-elimination the alkyl radical responsible for the induced reaction, These reactions of elimination produce two fragments, an alkyl radical and an ester molecule, from linear ''acetalic'' radical, or they could be isomerizations in the case of cyclanyloxy radicals. In these last cases, the isomerization creates an ester function corresponding to a new protected functionality as aldehyde, acid, or alcohol.

  DOI：

  10.1021/jo00096a018

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.
• Intramolecular Homolytic Displacements. 24. Simple Access to Glycidic Esters via Induced Decomposition of Peroxyketals Derived from Ethyl 2-(1-Hydroperoxyethyl)propenoate
  作者：Daniel Colombani、Bernard Maillard

  DOI：10.1021/jo00096a018

  日期：1994.8

  The synthetic potential of the homolytic-induced decomposition of peroxyketals peroxyketals derived from ethyl 2-(1-hydroperoxyethyl)propenoate to access glycidic esters was demonstrated. The propagation step of this free radical chain reaction proceeds via the addition of an alkyl radical to the double bond followed by S(H)i on the peroxidic bond with the production of an oxy radical, regenerating rapidly by beta-elimination the alkyl radical responsible for the induced reaction, These reactions of elimination produce two fragments, an alkyl radical and an ester molecule, from linear ''acetalic'' radical, or they could be isomerizations in the case of cyclanyloxy radicals. In these last cases, the isomerization creates an ester function corresponding to a new protected functionality as aldehyde, acid, or alcohol.