ethyl 2,3-epoxy-2-ethylbutanoate | 155701-32-9

• 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-ethylbutanoate
• 英文别名: Ethyl 2-ethyl-3-methyloxirane-2-carboxylate
• CAS: 155701-32-9
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: ATMCZQQRMFMITH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 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：

  methyl α-butylacetoacetate 在 过氧化乙酸叔丁酯 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 ethyl 2,3-epoxy-2-ethylbutanoate
  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

• Stereoselectivity of the intramolecular homolytic substitution in the induced decomposition of methacrylic-type peroxidic compounds
  作者：Daniel Colombani、Bernard Maillard

  DOI：10.1016/0040-4020(96)00914-3

  日期：1996.11

  The stereochemistry of the oxiranes, obtained by radical induced decomposition of various peroxydic compounds, was determined by NMR spectroscopy. The stereoselectivity of the intramolecular homolytic substitution on the peroxidic bond was discussed in relation to the effect of the reaction temperature and on the influence of structural factors such as the nature of the leaving and attacking radicals

  通过自由基诱导的各种过氧化合物的分解获得的环氧乙烷的立体化学通过NMR光谱测定。讨论了分子内均质取代对过氧化键的立体选择性，涉及反应温度的影响以及结构因素如离去基团和进攻基团的性质的影响。
• Synthesis of α,β-epoxyesters by homolytically induced decomposition of derivatives of ethyl 2-(1-hydroperoxyethyl)propenoate
  作者：Daniel Colombani、Bernard Maillard

  DOI：10.1039/c39940001259

  日期：——

  Decomposition of small amounts of tert-butyl peracetate at 110 °C in benzene solutions of derivatives of ethyl 2-(1-hydroperoxyethyl)propenoate afforded α,β-epoxyesters in good yields.

  在 2-(1-羟基过氧乙基)丙烯酸乙酯衍生物的苯溶液中，于 110°C 分解少量过乙酸叔丁酯，可得到δ,δ-环氧酯，收率良好。
• 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.
• Colombani, Daniel; Maillard, Bernard, Journal of the Chemical Society. Perkin transactions II, 1994, # 4, p. 745 - 752
  作者：Colombani, Daniel、Maillard, Bernard

  DOI：——

  日期：——