4-(6-cinnamoyloxyhexyloxy)-4''-cyano-p-terphenyl | 1384123-68-5

• 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: 4-(6-cinnamoyloxyhexyloxy)-4''-cyano-p-terphenyl
• 英文别名: 6-[4-[4-(4-cyanophenyl)phenyl]phenoxy]hexyl (E)-3-phenylprop-2-enoate
• CAS: 1384123-68-5
• 化学式: C₃₄H₃₁NO₃
• 分子量: 501.625
• InChiKey: FPVMOSZIOANHED-FSJBWODESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(6-cinnamoyloxyhexyloxy)-4''-cyano-p-terphenyl 生成
  参考文献：
  名称：

  Regioselectivity control of photodimerization of liquid-crystalline cinnamoyl compounds by phase variation: dual functionality of p-terphenyl substituent as a mesogen and a triplet sensitizer

  摘要：

  Cinnamoyl-functionalized liquid-crystalline (LC) compounds having a 4 ''-substituted [1,1';4',1 '']terphenyl (p-terphenyl) as mesogens were synthesized to investigate the abilities of the mesogen to act as a triplet sensitizer. UV (365 nm) irradiation of the LC compound having 4 ''-cyano-p-terphenyl in the crystalline and LC phases regioselectively produced the photodimers with a head-to-tail and a head-to-head cyclobutane unit, respectively. The p-terphenyl thus played the role of triplet sensitizer because the cinnamoyl group does not absorb 365 nm light. Due to the dual functionality of the p-terphenyl as the mesogen and the triplet sensitizer, we successfully performed the photochemical and regioselective cycloaddition to obtain two different LC dimers from one LC monomer. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.083
• 作为产物：
  描述：

  4-羟基-4'-溴联苯 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 27.5h， 生成 4-(6-cinnamoyloxyhexyloxy)-4''-cyano-p-terphenyl
  参考文献：
  名称：

  Regioselectivity control of photodimerization of liquid-crystalline cinnamoyl compounds by phase variation: dual functionality of p-terphenyl substituent as a mesogen and a triplet sensitizer

  摘要：

  Cinnamoyl-functionalized liquid-crystalline (LC) compounds having a 4 ''-substituted [1,1';4',1 '']terphenyl (p-terphenyl) as mesogens were synthesized to investigate the abilities of the mesogen to act as a triplet sensitizer. UV (365 nm) irradiation of the LC compound having 4 ''-cyano-p-terphenyl in the crystalline and LC phases regioselectively produced the photodimers with a head-to-tail and a head-to-head cyclobutane unit, respectively. The p-terphenyl thus played the role of triplet sensitizer because the cinnamoyl group does not absorb 365 nm light. Due to the dual functionality of the p-terphenyl as the mesogen and the triplet sensitizer, we successfully performed the photochemical and regioselective cycloaddition to obtain two different LC dimers from one LC monomer. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.083

文献信息

• Regioselectivity control of photodimerization of liquid-crystalline cinnamoyl compounds by phase variation: dual functionality of p-terphenyl substituent as a mesogen and a triplet sensitizer
  作者：Hideyuki Kihara、Yasuo Norikane、Masaru Yoshida

  DOI：10.1016/j.tet.2012.04.083

  日期：2012.7

  Cinnamoyl-functionalized liquid-crystalline (LC) compounds having a 4 ''-substituted [1,1';4',1 '']terphenyl (p-terphenyl) as mesogens were synthesized to investigate the abilities of the mesogen to act as a triplet sensitizer. UV (365 nm) irradiation of the LC compound having 4 ''-cyano-p-terphenyl in the crystalline and LC phases regioselectively produced the photodimers with a head-to-tail and a head-to-head cyclobutane unit, respectively. The p-terphenyl thus played the role of triplet sensitizer because the cinnamoyl group does not absorb 365 nm light. Due to the dual functionality of the p-terphenyl as the mesogen and the triplet sensitizer, we successfully performed the photochemical and regioselective cycloaddition to obtain two different LC dimers from one LC monomer. (c) 2012 Elsevier Ltd. All rights reserved.