(E,Z)-8-phenyl-7-octenal | 7020-95-3

• 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: (E,Z)-8-phenyl-7-octenal
• 英文别名: 8-phenyl-7-octenal；8-Phenyloct-7-enal
• CAS: 7020-95-3
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: NSFUOVANYCRVJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙酸,三氟-,(1,1-dimethylethyl)二甲基甲硅烷基酯 、 (E,Z)-8-phenyl-7-octenal 在 三乙胺 作用下， 以 苯 为溶剂， 以55%的产率得到(Z)-1-(tert-butyldimethylsiloxy)-(E,Z)-8-phenyl-1,7-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
• 作为产物：
  描述：

  2-苯基环辛烷-1-酮 在 氧气 作用下， 以 异丙醇 为溶剂， 反应 0.17h， 生成 5-己烯酸 、 (E,Z)-8-phenyl-7-octenal 、 苯乙酮
  参考文献：
  名称：

  圆偏振光下 2-苯基环烷酮的不对称光解：磁场效应的动力学模型

  摘要：

  已经在考虑中间体的系统间交叉 (ISC) 的动力学模型上研究了磁场效应 (MFE) 对涉及双自由基中间体的不对称光解。模拟了圆偏振光 (CPL) 照射下手性物质的对映体过量 (ee) 的变化，并获得了观察 MFE 的必要条件。外消旋 2-苯基环烷酮 (2-PCA) 与 CPL 的不对称光解已在存在和不存在磁场的情况下进行。由于 2-PCA 的各向异性 g 因子相当大，尽管未观察到 MFE，但在 90% 分解后，CPL 诱导的 ee 达到了几个百分点。2-PCA 在空气饱和溶液中的光解机理也已阐明。三重酰基-苄基双自由基，通过 2-PCA 的光化学 α-裂解形成，与溶解在溶液中的 O2 反应并导致形成苯乙酮和链烯酸。双分子...

  DOI：

  10.1246/bcsj.75.1223

文献信息

• Asymmetric Photolysis of 2-Phenylcycloalkanones with Circularly Polarized Light: A Kinetic Model for Magnetic Field Effects
  作者：Shigeru Kohtani、Masahide Sugiyama、Yoshihisa Fujiwara、Yoshifumi Tanimoto、Ryoichi Nakagaki

  DOI：10.1246/bcsj.75.1223

  日期：2002.6

  (MFE) on asymmetric photolysis involving a biradical intermediate have been investigated on a kinetic model where an intersystem crossing (ISC) of the intermediate is taken into account. Changes in the enantiomeric excesses (ee) of chiral substances with circularly polarized light (CPL) irradiation have been simulated, and the necessary conditions for observing the MFE were obtained. The asymmetric photolysis

  已经在考虑中间体的系统间交叉 (ISC) 的动力学模型上研究了磁场效应 (MFE) 对涉及双自由基中间体的不对称光解。模拟了圆偏振光 (CPL) 照射下手性物质的对映体过量 (ee) 的变化，并获得了观察 MFE 的必要条件。外消旋 2-苯基环烷酮 (2-PCA) 与 CPL 的不对称光解已在存在和不存在磁场的情况下进行。由于 2-PCA 的各向异性 g 因子相当大，尽管未观察到 MFE，但在 90% 分解后，CPL 诱导的 ee 达到了几个百分点。2-PCA 在空气饱和溶液中的光解机理也已阐明。三重酰基-苄基双自由基，通过 2-PCA 的光化学 α-裂解形成，与溶解在溶液中的 O2 反应并导致形成苯乙酮和链烯酸。双分子...
• 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.