(1E,3Z)-4-{o-[(1E,3Z)-3-chloro-4-phenyl-1,3-butadienyl]phenyl}-2-chloro-1-phenyl-1,3-butadiene | 1463930-92-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (1E,3Z)-4-{o-[(1E,3Z)-3-chloro-4-phenyl-1,3-butadienyl]phenyl}-2-chloro-1-phenyl-1,3-butadiene
• 英文别名: 1,2-bis[(1E,3Z)-3-chloro-4-phenylbuta-1,3-dienyl]benzene
• CAS: 1463930-92-8
• 化学式: C₂₆H₂₀Cl₂
• 分子量: 403.351
• InChiKey: NWDIUEVYMYQAPH-AURUYCJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (Z)-2-chloro-3-phenyl-2-propenal 、 o-xylylene(bistriphenylphospine) dibromide 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以55%的产率得到(1E,3Z)-4-{o-[(1E,3Z)-3-chloro-4-phenyl-1,3-butadienyl]phenyl}-2-chloro-1-phenyl-1,3-butadiene
  参考文献：
  名称：

  Novel arylated chloro- and methoxy-1,3-dibutadienes: Influence of substituents on molecular conformation and crystal packing

  摘要：

  Three novel arylated chloro- and methoxy-1,3-butadienes were prepared and studied by a combination of spectroscopic (UV/vis, IR and NMR) and X-ray crystallographic methods. Influence of substituent on the molecular conformation and crystal packing (i.e. intermolecular interactions) was studied. It was predicted that the differences in electronic and steric effects of two chlorine atoms in comparison to two methoxy groups as substituents at different locations in the molecule would provide various packing of the molecules and cause different assumptions for the photochemical behaviour. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.04.028

文献信息

• Synthesis and photochemical transformations of new butadiene chromophores: The influence of the nature and position of chlorine substituent on the photoinduced behaviour
  作者：Dragana Vuk、Dalia Potroško、Marija Šindler-Kulyk、Željko Marinić、Krešimir Molčanov、Biserka Kojić-Prodić、Irena Škorić

  DOI：10.1016/j.molstruc.2013.07.052

  日期：2013.11

  Abstract The photochemical behaviour of mono- and dichloro-substituted butadiene derivatives was studied at low concentrations. These compounds display diverse photochemical behaviour. The α -chloro derivatives photocyclize to give six-membered ring photoproducts. p -Chloro-substituted butadienes undergo intramolecular [2 + 2] cycloaddition followed by formation of benzobicyclic structures. The steric

  摘要 研究了单氯和二氯取代丁二烯衍生物在低浓度下的光化学行为。这些化合物显示出不同的光化学行为。α-氯衍生物光环化得到六元环光产物。对氯取代的丁二烯进行分子内 [2 + 2] 环加成，然后形成苯并双环结构。相对于 p 取代和位移构象异构体平衡，α 位氯的空间位阻导致平面性的更大偏差，并影响反应途径和产率。
• Thermal electrocyclization reactions II: benzooctatetraenes and benzodecapentaenes
  作者：Dragana Vuk、Željko Marinić、Krešimir Molčanov、Davor Margetić、Irena Škorić

  DOI：10.1016/j.tet.2013.12.027

  日期：2014.1

  Thermal electrocyclization reactions of benzooctatetraenes and benzodecapentaenes substituted with R=H, Cl, and methyl were studied experimentally and computationally. Methyl and unsubstituted benzooctatetraenes and benzodecapentaenes give the [4.2.0]bicyclooctadiene products by 8 pi,6 pi-electrocyclization. Chlorine substitution led to thermal rearrangement of the initially formed 8 pi,6 pi-electrocyclization intermediates to give unprecedented products. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel arylated chloro- and methoxy-1,3-dibutadienes: Influence of substituents on molecular conformation and crystal packing
  作者：Dragana Vuk、Krešimir Molčanov、Irena Škorić

  DOI：10.1016/j.molstruc.2014.04.028

  日期：2014.6

  Three novel arylated chloro- and methoxy-1,3-butadienes were prepared and studied by a combination of spectroscopic (UV/vis, IR and NMR) and X-ray crystallographic methods. Influence of substituent on the molecular conformation and crystal packing (i.e. intermolecular interactions) was studied. It was predicted that the differences in electronic and steric effects of two chlorine atoms in comparison to two methoxy groups as substituents at different locations in the molecule would provide various packing of the molecules and cause different assumptions for the photochemical behaviour. (C) 2014 Elsevier B.V. All rights reserved.