1-(para-cyanophenyl)-4-(para-methoxyphenyl)-buta-1E,3E-diene | 136795-67-0

• 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: 1-(para-cyanophenyl)-4-(para-methoxyphenyl)-buta-1E,3E-diene
• 英文别名: 1-(p-cyanophenyl)-4-(p-methoxyphenyl) buta-1-E,3-E, diene；(E,E)-4-[4-(4-methoxyphenyl)-1,3-butadienyl]benzonitrile；1-(p-methoxyphenyl)-4-(p-cyanophenyl)-buta-1E,3E-diene；4-[(1E,3E)-4-(4-methoxyphenyl)buta-1,3-dienyl]benzonitrile
• CAS: 136795-67-0
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: PQNZQXPGXOPWAO-ZUVMSYQZSA-N

物化性质

• 熔点：
  172-173 °C(Solv: ethanol (64-17-5))
• 沸点：
  475.6±38.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(para-cyanophenyl)-4-(para-methoxyphenyl)-buta-1E,3E-diene 在 吡啶 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 39.0h， 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：

  对氰基溴化苄 在 sodium hydride 作用下， 反应 72.0h， 生成 1-(para-cyanophenyl)-4-(para-methoxyphenyl)-buta-1E,3E-diene
  参考文献：
  名称：

  非常规霍纳-沃兹沃斯-埃蒙斯烯化产物的观察以及侧向乙基取代对固态荧光的影响

  摘要：

  供体-受体取代diphenylbutadienes，即1-（p -甲氧基苯基）-4-（p氰基苯基）丁1 ë，3 é -二烯（MCB）和1-（p - Ñ，Ñ -dimethylaminophenyl）-4- （p-氰基苯基）buta-1 E，3 E-二烯（ACB）在其固体中显示出与溶液中的荧光明显不同的荧光性质。红移吸收和发射光谱固态观察到的现象归因于J聚集体的形成。通过霍纳-沃兹沃思-埃蒙斯反应制备这些衍生物，其中膦酸酯 通过治疗获得 对氰基苄基溴 和 亚磷酸三乙酯 被压缩与相应 肉桂醛，也产生了非传统烯产物1-（p -甲氧基苯基）-4-（p氰基苯基）-4-（乙基）丁-1- ë，3 é -二烯（MCBE）和1-（p - Ñ，N-二甲氨基苯基）-4-（对氰基苯基）-4-（乙基）buta-1 E，3 E-二烯（ACBE）乙基丁二烯链上的取代基。这些产物的形成表明碱催化的1,3-迁移乙基从氧中心

  DOI：

  10.1039/b408748h

文献信息

• Effect of microheterogeneous media on the fluorescence and fluorescence probe properties of donor–acceptor diarylbutadienes
  作者：Anil K. Singh、Sriram Kanvah

  DOI：10.1039/b000586j

  日期：——

  Diarylbutadienes, namely 1-(para-cyanophenyl)-4-phenylbuta-1E,3E-diene (1), 1-(para-methoxyphenyl)-4-phenylbuta-1E,3E-diene (2), 1-(para-cyanophenyl)-4-(para-methoxyphenyl)-buta-1E,3E-diene (3) have been prepared and investigated for their absorption and fluorescence properties in homogeneous media of organic solvents, dioxane–water binary mixtures and in the microheterogeneous media of sodium dodecyl sulfate, cetyl trimethyl ammonium bromide and Triton-X-100 micelles. The fluorescence behaviour in various media has been correlated in terms of empirical solvent parameters such as Dimroth ET(30) and Kamlet–Taft π* values, and Kirkwood functions. A Linear correlation between solvent polarity and fluorescence properties is observed. In ethanol–methanol (1:1, v/v) matrix at 77 K, a blue-shifted fluorescence maximum with enhanced fluorescence quantum yields is observed for dienes 2 and 3. The singlet excited state of diene 3 is found to be highly polar in nature. The fluorescence peak intensity of dienes 1 and 2 and the fluorescence emission wavelength maximum (λf max) of diene 3 undergo significant changes upon changing the concentration of surfactants. The fluorescence properties of these dienes have been further used to characterize the micelles in terms of their critical micelle concentration and micropolarity.

  在有机溶剂、二噁烷和水的二元混合物的均相介质中，以及在二噁烷和水的微均相介质中，制备了二芳基丁二烯，即 1-(对氰基苯基)-4-苯基丁-1E,3E-二烯 (1)、1-(对甲氧基苯基)-4-苯基丁-1E,3E-二烯 (2)、1-(对氰基苯基)-4-(对甲氧基苯基)-丁-1E,3E-二烯 (3)，研究了它们的吸收和荧光特性、3E-diene (3)，并研究了它们在有机溶剂、二恶烷和水的二元混合物的均相介质以及十二烷基硫酸钠、十六烷基三甲基溴化铵和 Triton-X-100 胶束的微均相介质中的吸收和荧光特性。各种介质中的荧光行为都与经验溶剂参数相关，如 Dimroth ET(30) 和 KamletâTaft Ï* 值以及 Kirkwood 函数。观察到溶剂极性与荧光特性之间存在线性相关。在 77 K 的乙醇/甲醇（1:1，v/v）基质中，二烯 2 和 3 的荧光最大值发生蓝移，荧光量子产率增强。发现二烯 3 的单激发态具有高度极性。在改变表面活性剂浓度时，二烯 1 和 2 的荧光峰强度以及二烯 3 的荧光发射波长最大值（δ "f max）会发生显著变化。这些二烯的荧光特性被进一步用来描述胶束的临界胶束浓度和微极性。
• Sequential Cross-Coupling of 1,4-Bissilylbutadienes:  Synthesis of Unsymmetrical 1,4-Disubstituted 1,3-Butadienes
  作者：Scott E. Denmark、Steven A. Tymonko

  DOI：10.1021/ja0518373

  日期：2005.6.1

  A mild and general and stereospecific cross-coupling reaction of unsymmetrical 1,4-bissilyl-1,3-butadienes has been accomplished. By the use of either a benzyldimethylsilyl or 2-thienyldimethylsilyl unit at one end of the dienylsilanol, a selective cross-coupling could be effected under mildly basic conditions (KOTMS) to afford 4-aryl-1,3-dienylsilanes in excellent yield for a wide range of aryl and alkenyl coupling partners. The second cross-coupling could be effected cleanly by the action of TBAF with electron-rich or electron-poor halides. The sequential process could be telescoped into a "one pot" procedure with overall excellent yields of the unsymmetrical 1,4-diaryl-1,3-butadienes.
• Reversible Thermal and Photochemical Switching of Liquid Crystalline Phases and Luminescence in Diphenylbutadiene-Based Mesogenic Dimers
  作者：Shibu Abraham、V. Ajay Mallia、K. Vijayaraghavan Ratheesh、Nobuyuki Tamaoki、Suresh Das

  DOI：10.1021/ja061575k

  日期：2006.6.1

  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.
• Observation of a non-conventional Horner–Wadsworth–Emmons olefination product and the effect of the lateral ethyl substitution on the solid state fluorescence
  作者：Riju Davis、Shibu Abraham、Nigam P. Rath、Suresh Das

  DOI：10.1039/b408748h

  日期：——

  henyl)-4-(ethyl)buta-1E,3E-diene (MCBE) and 1-(p-N,N-dimethylaminophenyl)-4-(p-cyanophenyl)-4-(ethyl)buta-1E,3E-diene (ACBE), which bear an ethyl group substituent on their butadiene chain. The formation of these products suggests a base-catalyzed 1,3-migration of an ethyl group from an oxygen center to the benzylic position in the initially formed phosphonate. The presence of the ethyl group in an

  供体-受体取代diphenylbutadienes，即1-（p -甲氧基苯基）-4-（p氰基苯基）丁1 ë，3 é -二烯（MCB）和1-（p - Ñ，Ñ -dimethylaminophenyl）-4- （p-氰基苯基）buta-1 E，3 E-二烯（ACB）在其固体中显示出与溶液中的荧光明显不同的荧光性质。红移吸收和发射光谱固态观察到的现象归因于J聚集体的形成。通过霍纳-沃兹沃思-埃蒙斯反应制备这些衍生物，其中膦酸酯 通过治疗获得 对氰基苄基溴 和 亚磷酸三乙酯 被压缩与相应 肉桂醛，也产生了非传统烯产物1-（p -甲氧基苯基）-4-（p氰基苯基）-4-（乙基）丁-1- ë，3 é -二烯（MCBE）和1-（p - Ñ，N-二甲氨基苯基）-4-（对氰基苯基）-4-（乙基）buta-1 E，3 E-二烯（ACBE）乙基丁二烯链上的取代基。这些产物的形成表明碱催化的1,3-迁移乙基从氧中心