2-methyl-3-cyclohexene-1-carboxaldehyde dimethyl acetal | 103984-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-3-cyclohexene-1-carboxaldehyde dimethyl acetal
• 英文别名: 4-Dimethoxymethyl-3-methyl-cyclohexen-(1)；4-(dimethoxymethyl)-3-methylcyclohexene
• CAS: 103984-01-6
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: QOQXZPUQHHWPJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  [(2E,7E)-8-methoxyocta-2,7-dien-3-yl]-trimethylsilane 生成 2-methyl-3-cyclohexene-1-carboxaldehyde dimethyl acetal
  参考文献：
  名称：

  Hudson Christine M., Moeller Kevin D., J. Amer. Chem. Soc, 116 (1994) N 8, S 3347-3356

  摘要：

  DOI：

文献信息

• Intramolecular Anodic Olefin Coupling Reactions and the Use of Vinylsilanes
  作者：Christine M. Hudson、Kevin D. Moeller

  DOI：10.1021/ja00087a021

  日期：1994.4

  Intramolecular anodic olefin coupling reactions involving vinylsilane groups have been studied. It was found that the previously successful predictive model for olefin coupling reactions based on an electrophilic attack of a radical cation onto an olefin did not successfully predict product formation for olefin coupling reactions involving vinylsilane terminating groups. Instead, these reactions were best described by viewing the initial addition of the radical cation to an olefin as if it occurred in a reversible ''radical-like'' fashion, in addition, reactions using a temporary silicon tether were shown to be compatible with the formation of quaternary carbons with control of relative stereochemistry. These reactions helped highlight the compatibility of the anodic olefin coupling reactions with extremely sensitive substrates. Finally, the results reported suggest that the mass balance of the intramolecular anodic olefin coupling reaction depends on the ease with which the initially formed cyclized product undergoes the second oxidation step.