(Z)-1-phenyl-7-methyl-1,6-octadiene | 128900-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-1-phenyl-7-methyl-1,6-octadiene
• 英文别名: N-((Z)-7-methyl-octa-1,6-dienyl)benzene；[(1Z)-7-methylocta-1,6-dienyl]benzene
• CAS: 128900-83-4
• 化学式: C₁₅H₂₀
• 分子量: 200.324
• InChiKey: SENUOBRKZBXPIH-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-phenyl-7-methyl-1,6-octadiene 在 C₄₂H₃₆F₁₀IrN₄⁽¹⁺⁾*F₆P^(1-) 作用下， 以 二甲基亚砜 为溶剂， 反应 38.0h， 以81.818%的产率得到
  参考文献：
  名称：

  [2+2]苯乙烯环加成的可见光能量转移催化

  摘要：

  髋关节呈方形：在铱(III)聚吡啶络合物存在下，苯乙烯在可见光照射下参与[2+2]环加成反应。与之前报道的可见光光氧化还原催化相反，该过程的机制涉及通过能量转移而不是电子转移进行光敏化。

  DOI：

  10.1002/anie.201204835
• 作为产物：
  描述：

  6-methylhept-5-en-1-ol 在 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 反应 2.83h， 生成 (Z)-1-phenyl-7-methyl-1,6-octadiene
  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

• Visible Light Photocatalysis of [2+2] Styrene Cycloadditions by Energy Transfer
  作者：Zhan Lu、Tehshik P. Yoon

  DOI：10.1002/anie.201204835

  日期：2012.10.8

  Hip to be square: Styrenes participate in [2+2] cycloadditions upon irradiation with visible light in the presence of an iridium(III) polypyridyl complex. In contrast to previous reports of visible light photoredox catalysis, the mechanism of this process involves photosensitization by energy transfer and not electron transfer.

  髋关节呈方形：在铱(III)聚吡啶络合物存在下，苯乙烯在可见光照射下参与[2+2]环加成反应。与之前报道的可见光光氧化还原催化相反，该过程的机制涉及通过能量转移而不是电子转移进行光敏化。
• 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.