(E)-1-(4-hydroxyphenyl)-1-phenyl-2-(4-chlorophenyl) butylene | 1401092-65-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-(4-hydroxyphenyl)-1-phenyl-2-(4-chlorophenyl) butylene
• 英文别名: 4-[(E)-2-(4-chlorophenyl)-1-phenylbut-1-enyl]phenol
• CAS: 1401092-65-6
• 化学式: C₂₂H₁₉ClO
• 分子量: 334.845
• InChiKey: QDIQSMHDYJQBCS-QURGRASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  六氟磷酸钾 、 (η6-chlorobenzene)(η5-cyclopentadienyl)iron(II) hexafluorophosphate 、 (E)-1-(4-hydroxyphenyl)-1-phenyl-2-(4-chlorophenyl) butylene 、 (Z)-1-(4-hydroxyphenyl)-1-phenyl-2-(4-chlorophenyl) butylene 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 生成 (E)-[(η⁵-cyclopentadienyl)-Fe-(η⁶-1-(4-phenoxy)-1-phenyl-2-(4-chlorophenyl)butylene)] hexafluorophosphate 、 (Z)-[(η⁵-cyclopentadienyl)-Fe-(η⁶-1-(4-phenoxy)-1-phenyl-2-(4-chlorophenyl)butylene)] hexafluorophosphate
  参考文献：
  名称：

  Synthesis, spectroscopic characterization, and molecular structure of triphenyl butene derivatives containing a cyclopentadienyl iron unit

  摘要：

  Three hydroxyl substituted triphenyl butene compounds (PHB) and their derivatives containing a cyclopentadienyl iron (PHB-Fc) unit were efficiently synthesized. The synthesis involved the McMurry cross-coupling reaction of appropriate ketones and the nucleophilic aromatic substitution (SNAr) reaction of (eta(6)-chlorobenzene) (eta(5)-cyclopentadienyl) iron hexafluorophosphate (Fc-Cl). The target compounds were characterized by IR, H-1 NMR, C-13 NMR, and MS. Their photophysical processes were investigated by UV-Vis absorption and fluorescence emission spectra in acetonitrile. The geometric structure was optimized based on the density functional theory at the B3LYP level. Theoretical results reveal that electron transfer occurred from the HOMO to the LUMO in PHB-Fc. The change in electron distribution subsequently led to the improved second-order optical susceptibility of PHB-Fc. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.03.056
• 作为产物：
  描述：

  4-氯苯丙酮 、 4-羟基-二苯甲酮 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (E)-1-(4-hydroxyphenyl)-1-phenyl-2-(4-chlorophenyl) butylene 、 (Z)-1-(4-hydroxyphenyl)-1-phenyl-2-(4-chlorophenyl) butylene
  参考文献：
  名称：

  Synthesis, spectroscopic characterization, and molecular structure of triphenyl butene derivatives containing a cyclopentadienyl iron unit

  摘要：

  Three hydroxyl substituted triphenyl butene compounds (PHB) and their derivatives containing a cyclopentadienyl iron (PHB-Fc) unit were efficiently synthesized. The synthesis involved the McMurry cross-coupling reaction of appropriate ketones and the nucleophilic aromatic substitution (SNAr) reaction of (eta(6)-chlorobenzene) (eta(5)-cyclopentadienyl) iron hexafluorophosphate (Fc-Cl). The target compounds were characterized by IR, H-1 NMR, C-13 NMR, and MS. Their photophysical processes were investigated by UV-Vis absorption and fluorescence emission spectra in acetonitrile. The geometric structure was optimized based on the density functional theory at the B3LYP level. Theoretical results reveal that electron transfer occurred from the HOMO to the LUMO in PHB-Fc. The change in electron distribution subsequently led to the improved second-order optical susceptibility of PHB-Fc. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.03.056