(E,E)-1,4-di(o,p-bis(trifluoromethyl)phenyl)-1,3-butadiene | 848863-56-9

• 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,E)-1,4-di(o,p-bis(trifluoromethyl)phenyl)-1,3-butadiene
• 英文别名: 1-[(1E,3E)-4-[2,4-bis(trifluoromethyl)phenyl]buta-1,3-dienyl]-2,4-bis(trifluoromethyl)benzene
• CAS: 848863-56-9
• 化学式: C₂₀H₁₀F₁₂
• 分子量: 478.28
• InChiKey: WZYWKKVPWHCHEF-ZPUQHVIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (E,E)-1,4-di(o,p-bis(trifluoromethyl)phenyl)-1,3-butadiene 反应 15.0h， 以80%的产率得到
  参考文献：
  名称：

  Trifluoromethyl Groups in Crystal Design of 1,4-Diphenyl-1,3-butadienes for Topochemical [2 + 2] Photodimerization

  摘要：

  UV irradiation of the powdered crystalline sample of each of three (EE)-1,4-di(trifluoromethyl-substituted)phenyl-1,3-butadienes (1-3) was found to yield a single [2 + 2] cycloaddition product in the solid state. Moreover, upon irradiation, the crystalline samples of two (EE)-1,4-di(trifluoromethyl- and fluorine-substituted)phenyl-1,3-butadienes (4, 5) undergo a similar conversion to afford a [2 + 2] cycloaddition product, respectively. Our observations suggest that trifluoromethyl groups can be used to direct 1,4-diphenyl-1,3-butadiene molecules to form a parallel, offset-stacked orientation suitable for topochemical [2 + 2] cycloaddition.

  DOI：

  10.1021/ol0475111
• 作为产物：
  描述：

  2,4-双(三氟甲基)苯甲醛 在 sodium hydride 作用下， 生成 (E,E)-1,4-di(o,p-bis(trifluoromethyl)phenyl)-1,3-butadiene
  参考文献：
  名称：

  Trifluoromethyl Groups in Crystal Design of 1,4-Diphenyl-1,3-butadienes for Topochemical [2 + 2] Photodimerization

  摘要：

  UV irradiation of the powdered crystalline sample of each of three (EE)-1,4-di(trifluoromethyl-substituted)phenyl-1,3-butadienes (1-3) was found to yield a single [2 + 2] cycloaddition product in the solid state. Moreover, upon irradiation, the crystalline samples of two (EE)-1,4-di(trifluoromethyl- and fluorine-substituted)phenyl-1,3-butadienes (4, 5) undergo a similar conversion to afford a [2 + 2] cycloaddition product, respectively. Our observations suggest that trifluoromethyl groups can be used to direct 1,4-diphenyl-1,3-butadiene molecules to form a parallel, offset-stacked orientation suitable for topochemical [2 + 2] cycloaddition.

  DOI：

  10.1021/ol0475111