(E,Z)-1-methoxy-7-methyl-1,6-octadiene | 138236-33-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,Z)-1-methoxy-7-methyl-1,6-octadiene
• 英文别名: 1-methoxy-7-methylocta-1,6-diene
• CAS: 138236-33-6
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: ZKGWPONGWWMTFS-UHFFFAOYSA-N

物化性质

• 沸点：
  215.1±19.0 °C(Predicted)
• 密度：
  0.824±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E,Z)-1-methoxy-7-methyl-1,6-octadiene 在 2,6-二甲基吡啶 、 lithium perchlorate 作用下， 以 甲醇 为溶剂， 以17%的产率得到1-(dimethoxymethyl)-2-prop-1-en-2-ylcyclopentane
  参考文献：
  名称：

  氧化有机电化学：一种新型富电子烯烃的分子内偶联

  摘要：

  氧化环化反应是令人感兴趣的，因为它们允许产生碳-碳键和环的形成而不会损失分子的整体功能。有机电化学似乎非常适合引发此类反应，因为它可以在预设电位、中性条件下选择性氧化富电子官能团，并且不需要化学试剂。不幸的是，只有少数阳极反应会导致直接形成碳-碳键。此外，只有少数这些反应已被证明通常可用于引发分子内环化反应。作者在此报告了他们为此目的开发富电子烯烃的阳极偶联的初步努力。

  DOI：

  10.1021/ja00172a035

文献信息

• 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.