(1E,3E)-1-(4-cyanophenyl)-4-(4-hydroxyphenyl)-1,3-butadiene | 898288-97-6

• 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: (1E,3E)-1-(4-cyanophenyl)-4-(4-hydroxyphenyl)-1,3-butadiene
• 英文别名: 1-(p-cyanophenyl)-4-(4-hydroxyphenyl) buta-1-E,3-E, diene；1-(p-cyanophenyl)-4-(p-hydroxyphenyl)-buta-1E,3E-diene；4-[(1E,3E)-4-(4-Hydroxyphenyl)-1,3-butadien-1-yl]benzonitrile；4-[(1E,3E)-4-(4-hydroxyphenyl)buta-1,3-dienyl]benzonitrile
• CAS: 898288-97-6
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: SJDJNBSEXACHPC-ZPUQHVIOSA-N

物化性质

• 熔点：
  220-222 °C
• 沸点：
  490.2±38.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.02
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1E,3E)-1-(4-cyanophenyl)-4-(4-hydroxyphenyl)-1,3-butadiene 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.0h， 生成 11-[4-[(1E,3E)-4-(4-cyanophenyl)buta-1,3-dienyl]phenoxy]undecyl [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] carbonate
  参考文献：
  名称：

  Reversible Thermal and Photochemical Switching of Liquid Crystalline Phases and Luminescence in Diphenylbutadiene-Based Mesogenic Dimers

  摘要：

  The synthesis and study of the photo- and thermoresponsive behavior of a series of novel asymmetric mesogenic dimers, consisting of a cholesterol moiety linked to a diphenylbutadiene chromophore via flexible alkyl chains are reported. These mesogenic dimers possess the combined glass forming properties of the cholesterol moiety and the photochromic and luminescent properties of the butadiene moiety. Photoinduced cis/trans isomerization of the butadiene chromophore in these materials could be utilized to bring about an isothermal phase transition from the smectic to the cholesteric state. By photochemically controlling the cis/trans isomer ratio, the pitch of the cholesteric could be continuously varied making it possible to tune the color of the film over the entire visible region, and the color images thus generated could be stabilized by converting them to N* glasses. These materials were also polymorphic, exhibiting two crystalline forms possessing distinctly different fluorescence properties. The ability to thermally switch these materials from one crystalline form to the other in a reversible manner also makes them useful for recording fluorescent images.

  DOI：

  10.1021/ja061575k
• 作为产物：
  描述：

  1-(para-cyanophenyl)-4-(para-methoxyphenyl)-buta-1E,3E-diene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到(1E,3E)-1-(4-cyanophenyl)-4-(4-hydroxyphenyl)-1,3-butadiene
  参考文献：
  名称：

  Reversible Thermal and Photochemical Switching of Liquid Crystalline Phases and Luminescence in Diphenylbutadiene-Based Mesogenic Dimers

  摘要：

  The synthesis and study of the photo- and thermoresponsive behavior of a series of novel asymmetric mesogenic dimers, consisting of a cholesterol moiety linked to a diphenylbutadiene chromophore via flexible alkyl chains are reported. These mesogenic dimers possess the combined glass forming properties of the cholesterol moiety and the photochromic and luminescent properties of the butadiene moiety. Photoinduced cis/trans isomerization of the butadiene chromophore in these materials could be utilized to bring about an isothermal phase transition from the smectic to the cholesteric state. By photochemically controlling the cis/trans isomer ratio, the pitch of the cholesteric could be continuously varied making it possible to tune the color of the film over the entire visible region, and the color images thus generated could be stabilized by converting them to N* glasses. These materials were also polymorphic, exhibiting two crystalline forms possessing distinctly different fluorescence properties. The ability to thermally switch these materials from one crystalline form to the other in a reversible manner also makes them useful for recording fluorescent images.

  DOI：

  10.1021/ja061575k

文献信息

• Synthesis of α,ω-Diarylbutadienes and -Hexatrienes via Decarboxylative Coupling of Cinnamic Acids with Vinyl Bromides under Palladium Catalysis
  作者：Mana Yamashita、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol9027896

  日期：2010.2.5

  Readily available cinnamic acid derivatives such as ferulic acid couple with β-bromostyrenes and 1-bromo-4-phenylbutadiene under palladium catalysis accompanied by decarboxylation to produce the corresponding α,ω-diarylbutadienes and -hexatrienes, respectively. Some of the products exhibit solid-state fluorescence.

  易得的肉桂酸衍生物（如阿魏酸）在钯催化下与β-溴苯乙烯和1-溴-4-苯基丁二烯偶合，并伴随脱羧反应分别生成相应的α，ω-二芳基丁二烯和-己三烯。一些产品表现出固态荧光。
• Light induced generation of stable blue phase in photoresponsive diphenylbutadiene based mesogen
  作者：Ratheesh K. Vijayaraghavan、Shibu Abraham、D. S. Shankara Rao、S. Krishna Prasad、Suresh Das

  DOI：10.1039/b926524d

  日期：——

  Light induced isothermal phase transition leading from smectic A* phase to a stable blue phase was achieved via photoisomerization of a chiral diphenylbutadiene based mesogen.

  通过基于手性二苯基丁二烯的介晶的光异构化实现了从近晶A*相到稳定蓝相的光诱导等温相变。