Methyl 3,3-dimethyl-2-trimethylsilylperoxybutanoate | 64771-61-5

• 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: Methyl 3,3-dimethyl-2-trimethylsilylperoxybutanoate
• CAS: 64771-61-5
• 化学式: C₁₀H₂₂O₄Si
• 分子量: 234.368
• InChiKey: XBCJFIQBTRMAGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  65 °C(Press: 6 Torr)
• 密度：
  0.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 3,3-dimethyl-2-trimethylsilylperoxybutanoate 在 甲醇 作用下， 生成 Methylhydroperoxyacetat
  参考文献：
  名称：

  Cyclic peroxides. 61. Synthesis of .alpha.-hydroperoxy esters by singlet oxygenation of ketene acetals

  摘要：

  DOI：

  10.1021/jo00400a029
• 作为产物：
  描述：

  三甲基乙酸甲酯 在 氧气 、 tetraphenylporphyrin 作用下， 生成 Methyl 3,3-dimethyl-2-trimethylsilylperoxybutanoate
  参考文献：
  名称：

  Cyclic peroxides. 61. Synthesis of .alpha.-hydroperoxy esters by singlet oxygenation of ketene acetals

  摘要：

  DOI：

  10.1021/jo00400a029

文献信息

• Photooxygenation of silyl ketene acetals: dioxetanes as precursors to .alpha.-silylperoxy esters in the silatropic ene reaction
  作者：Waldemar Adam、Xiaoheng Wang

  DOI：10.1021/jo00015a030

  日期：1991.7

  Photooxygenation of silyl ketene acetals afforded dioxetanes, which subsequently underwent secondary reactions to give rearrangement products (alpha-silylperoxy esters, major products) and cleavage products (pivalaldehyde, minor product). The kinetics of these reactions were studied by NMR and chemiluminescence. The activation energy of the chemiluminescent cleavage process was 2-3 kcal/mol higher than that of the rearrangement. In the presence of catalytic amounts of CF3COCF3 or CF3COCH3, the (E)-silyl ketene acetals rearranged into their Z isomers. Photooxygenation of the (E)- and (Z)-silyl ketene acetals showed that the [2 + 2] cycloaddition was rigorously diastereoselective. Trapping experiments with acetaldehyde confirmed the intermediacy of 1,4-zwitterions in the rearrangement of the (E)- and (Z)-dioxetanes into alpha-silylperoxy esters, but such intermediates were not detected during the photooxygenation of the silyl ketene acetals; the latter proceeds presumably via perepoxides.
• ADAM W.; DEL FIERRO J., J. ORG. CHEM., 1978, 43, NO 6, 1159-1161
  作者：ADAM W.、 DEL FIERRO J.

  DOI：——

  日期：——