trimethylsilyl 3,3-dimethyl-2-<(trimethylsilyl)peroxy>butyrate | 36156-91-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: trimethylsilyl 3,3-dimethyl-2-<(trimethylsilyl)peroxy>butyrate
• 英文别名: trimethylsilyl 3,3-dimethyl-2-[(trimethylsilyl)peroxy]butyrate；Trimethylsilyl-3,3-dimethyl-2-trimethylsilylperoxybutyrat；Trimethylsilyl 3,3-dimethyl-2-trimethylsilylperoxybutanoate
• CAS: 36156-91-9
• 化学式: C₁₂H₂₈O₄Si₂
• 分子量: 292.523
• InChiKey: GGHOSRXQXJXEGL-UHFFFAOYSA-N

物化性质

• 沸点：
  251.3±23.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  trimethylsilyl 3,3-dimethyl-2-<(trimethylsilyl)peroxy>butyrate 在 甲醇 作用下， 生成 2-t-butyl-2-hydroperoxyacetic acid
  参考文献：
  名称：

  Cyclic peroxides. 52. .alpha.-Peroxylactones via dehydrative cyclization of .alpha.-hydroperoxy acids

  摘要：

  DOI：

  10.1021/ja00459a038
• 作为产物：
  描述：

  3,3-二甲基-1-丁酸 在 氧气 、 tetraphenylporphyrin 作用下， 生成 trimethylsilyl 3,3-dimethyl-2-<(trimethylsilyl)peroxy>butyrate
  参考文献：
  名称：

  Cyclic peroxides. 52. .alpha.-Peroxylactones via dehydrative cyclization of .alpha.-hydroperoxy acids

  摘要：

  DOI：

  10.1021/ja00459a038

文献信息

• The Synthesis of 1,2,4-Trioxan-5-ones
  作者：Charles W. Jefford、Jane Currie、Geoffrey D. Richardson、Jean-Claude Rossier

  DOI：10.1002/hlca.19910740612

  日期：1991.9.18

  Several 3,6-substituted 1,2,4-trioxan-5-ones have been prepared in good yield by condensing aldehydes and ketones with trimethylsilyl α-[(trimethylsilyl)peroxy]alkanoates in the presence of trimethylsilyl trifluoromethane sulfonate as catalyst.

  在三甲基甲硅烷基三氟甲烷磺酸盐作为催化剂的存在下，通过将醛和酮与三甲基甲硅烷基α-[（三甲基甲硅烷基）过氧]链烷酸酯缩合，可以高收率制备数个3,6-取代的1,2,4-三恶烷-5-酮。
• The reaction of trimethylsilyl α-trimethylsilylperoxy esters with ketones and aldehydes. A simple, efficient synthesis of 1,2,4-trioxan-5-ones
  作者：Charles W. Jefford、Jean-Claude Rossier、Geoffrey D. Richardson

  DOI：10.1039/c39830001064

  日期：——

  The title compounds readily react in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulphonate to give the corresponding 3,6-substituted 1,2,4-trioxan-5-ones in good yields.

  标题化合物容易在催化量的三氟甲磺酸三甲基甲硅烷基酯存在下反应，以高收率得到相应的3,6-取代的1,2,4-三恶烷-5-酮。
• 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.; ALZERRECA A.; LIU J.-C.; YANY F., J. AMER. CHEM. SOC. <JACS-AT>, 1977, 99, NO 17, 5768-5773
  作者：ADAM W.、 ALZERRECA A.、 LIU J.-C.、 YANY F.

  DOI：——

  日期：——