ethyl 2,3-epoxy-2-<5-(formyloxy)pentyl>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-<5-(formyloxy)pentyl>butanoate
• 英文别名: Ethyl 2-(5-formyloxypentyl)-3-methyloxirane-2-carboxylate
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: SUQBHFPKWXWUKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 3-hydroperoxy-2-methylenebutanoate 在 过氧化乙酸叔丁酯 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 12.0h， 生成 ethyl 2,3-epoxy-2-<5-(formyloxy)pentyl>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

• Synthesis of methacrylic-type peroxidic compounds and study of their homolytic induced decomposition in solution
  作者：Daniel Colombani

  DOI：10.1016/s0040-4020(96)01180-5

  日期：1997.2

  unsaturated peroxidic compounds have been prepared, characterized and inductively decomposed in various solvents to afford the corresponding oxiranes. The reaction proceeded by a radical chain mechanism and was initiated either by thermolysis of added t-butyl peracetate at 110°C or AIBN at 80°C, or by autoxidation of BEt3 at 20°C. The studied peroxyderivatives were designed to generate oxyl radicals reacting

  已经制备了各种不饱和的过氧化物，对其进行了表征并在各种溶剂中进行了感应分解，从而提供了相应的环氧乙烷。该反应通过自由基链机理进行，并且通过添加的过乙酸叔丁基酯在110℃或AIBN在80℃下热解或在20℃下BEt 3的自氧化来引发。所研究的过氧衍生物被设计为产生羟基，该羟基通过异构化反应（例如分子内1，5-氢原子转移，环状结构的环化或β断裂），断裂或氢原子转移至溶剂中而生成官能烷基。
• 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.