1-methyl-2-(dimethylphenylsilyl)-2-propenyl hydroperoxide | 156518-07-9

• 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: 1-methyl-2-(dimethylphenylsilyl)-2-propenyl hydroperoxide
• 英文别名: 3-hydroperoxybut-1-en-2-yl-dimethyl-phenylsilane
• CAS: 156518-07-9
• 化学式: C₁₂H₁₈O₂Si
• 分子量: 222.359
• InChiKey: DBBAQRWGGFIWCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-methyl-2-(dimethylphenylsilyl)-2-propenyl hydroperoxide 生成 (S)-3-(Dimethyl-phenyl-silanyl)-but-3-en-2-yl-hydroperoxide
  参考文献：
  名称：

  Biocatalytic kinetic resolution of hydroperoxy vinylsilanes by horseradish peroxidase (HRP) and lipases, a comparative study

  摘要：

  The kinetic resolution of hydroperoxy vinylsilanes 1 has been investigated by the horseradish-peroxidase(HRP)-catalyzed reduction with guaiacol and by the acetylation with isopropenyl acetate in the presence of various lipases. The best results (ee values up to 89% at 48% conversion) were obtained for the lipase-catalyzed reactions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00197-3
• 作为产物：
  描述：

  (E)-dimethyl(1-methyl-1-propenyl)phenylsilane 以75%的产率得到
  参考文献：
  名称：

  Adam Waldemar, Richter Markus J., J. Org. Chem., 59 (1994) N 12, S 3335- 3340

  摘要：

  DOI：

文献信息

• Regioselectivity of the Singlet Oxygen Ene Reaction (Schenck Reaction) with Vinylsilanes
  作者：Waldemar Adam、Markus J. Richter

  DOI：10.1021/jo00091a020

  日期：1994.6

  The ene reaction-of singlet oxygen and vinylsilanes 1 with various substitution patterns and double-bond geometry has been studied. beta-Silyl allylic hydroperoxides 2 were the major products of the photooxygenation, accompanied by smaller amounts of alpha,beta-unsaturated ketones 3. The latter derive from decomposition of the regioisomeric alpha-hydroperoxy silanes 4 by elimination of silanol. Regioselectivities up to 97:3 were observed for vinylsilanes with a methyl group geminal to the silyl group and with cyclic derivatives. Z-Configurated substrates showed lower regioselectivity and reactivity. Elongation of the carbon chain at the geminal position also increased the amount enone formed. These results are rationalized in terms of stereoelectronic effects imposed by the silyl group on the ring-opening of the perepoxide intermediate.