2-(1-methoxy-2-(trimethylsilyl)ethyl)cyclohexane-1-carboxaldehyde dimethyl acetal | 134923-02-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-methoxy-2-(trimethylsilyl)ethyl)cyclohexane-1-carboxaldehyde dimethyl acetal
• 英文别名: [2-[2-(dimethoxymethyl)cyclohexyl]-2-methoxyethyl]-trimethylsilane
• CAS: 134923-02-7
• 化学式: C₁₅H₃₂O₃Si
• 分子量: 288.503
• InChiKey: HMSGIWBHCJKQFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (2-trimethylsilylethylidene)triphenylphosphorane 在 2,6-二甲基吡啶 、 正丁基锂 、 lithium perchlorate 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 51.67h， 生成 2-(1-methoxy-2-(trimethylsilyl)ethyl)cyclohexane-1-carboxaldehyde dimethyl acetal
  参考文献：
  名称：

  Intramolecular anodic olefin coupling reactions: a useful method for carbon-carbon bond formation

  摘要：

  The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The enol ethers could be coupled to simple alkyl olefins, styrenes, and allylsilanes in isolated yields ranging from 57 to 84%. The reactions were found to be effective for generating both five- and six-membered rings. The best conditions for cyclization utilized a reticulated vitreous carbon anode, constant-current conditions in an undivided cell, and a lithium perchlorate in either 50% methanol/tetrahydrofuran or 20% methanol/dichloromethane electrolyte solution. The use of an allylsilane as one of the participating olefins allowed for the regiospecific formation of olefinic products. In addition to the olefinic products, these reactions produced a small amount of a cyclized ether product in which the silyl group had not been eliminated. Deuterium-labeling studies showed that at least half of this ether byproduct arose from intramolecular migration of the methoxy group that was initially part of the starting enol ether to the carbon-beta to the silyl group. Intramolecular migration reactions of this type were found to participate in a number of the reported cyclization reactions.

  DOI：

  10.1021/ja00019a038

文献信息

• Intramolecular anodic olefin coupling reactions: the use of allylsilanes
  作者：Kevin D. Moeller、Christine M. Hudson

  DOI：10.1016/s0040-4039(00)79910-2

  日期：1991.5

  The use of allylsilanes as directing groups in the intramolecular electrochemical coupling of electron rich olefins has been examined. The allylsilanes were shown to provide an effective means for controlling product selectivity, and led to the formation of five- and six-membered ring products in 59–84% isolated yields.

  已经研究了在富电子烯烃的分子内电化学偶合中使用烯丙基硅烷作为指导基团。烯丙基硅烷显示出提供了一种控制产物选择性的有效手段，并导致了五元和六元环产物的形成，分离产率为59-84％。
• Intramolecular anodic olefin coupling reactions: a useful method for carbon-carbon bond formation
  作者：Christine M. Hudson、Mohammad R. Marzabadi、Kevin D. Moeller、Dallas G. New

  DOI：10.1021/ja00019a038

  日期：1991.9

  The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The enol ethers could be coupled to simple alkyl olefins, styrenes, and allylsilanes in isolated yields ranging from 57 to 84%. The reactions were found to be effective for generating both five- and six-membered rings. The best conditions for cyclization utilized a reticulated vitreous carbon anode, constant-current conditions in an undivided cell, and a lithium perchlorate in either 50% methanol/tetrahydrofuran or 20% methanol/dichloromethane electrolyte solution. The use of an allylsilane as one of the participating olefins allowed for the regiospecific formation of olefinic products. In addition to the olefinic products, these reactions produced a small amount of a cyclized ether product in which the silyl group had not been eliminated. Deuterium-labeling studies showed that at least half of this ether byproduct arose from intramolecular migration of the methoxy group that was initially part of the starting enol ether to the carbon-beta to the silyl group. Intramolecular migration reactions of this type were found to participate in a number of the reported cyclization reactions.