(2Z,4E)-5-(4-methoxyphenyl)-2-phenylpenta-2,4-dienenitrile | 1313706-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2Z,4E)-5-(4-methoxyphenyl)-2-phenylpenta-2,4-dienenitrile
• 英文别名: 5-(p-methoxyphenyl)-2-phenylpenta-2,4-dienenitrile
• CAS: 1313706-55-6
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: OLYYXMVSOMZEEA-ZUZMZGHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33.02
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-甲氧基肉桂醛 、 苯乙腈 在 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 10.0h， 以81%的产率得到(2Z,4E)-5-(4-methoxyphenyl)-2-phenylpenta-2,4-dienenitrile
  参考文献：
  名称：

  简便地制备α-氰基-α，ω-二芳基低聚二亚乙烯基：一类新型的可彩色调谐的固体发射体

  摘要：

  有效的Knoevenagel缩合反应用于构建一系列的α-氰基-α，ω-二芳基寡聚谷氨酰胺，它们在固态下显示出显着的荧光发射。在研究共轭长度对荧光性质的影响时，我们发现二烯结构显示出优异的固态发光。此外，可以通过在末端芳基上引入供体或受体官能团来调节发光颜色。通过向α-氰基-α，ω-二芳基二亚乙烯基部分添加不同的官能团，可以实现可见光区域的全色发射。阐明了结构与属性之间的关系，并讨论了一些观察结果，例如取代位置效应。

  DOI：

  10.1002/asia.201500473

文献信息

• Structural and computational studies of 2,5-diarylpenta-2,4-dienenitriles
  作者：A. Manimekalai、A. Balamurugan

  DOI：10.1016/j.molstruc.2011.03.060

  日期：2011.5

  2,5-Diarylpenta-2,4-dienenitriles 1-9 were synthesized and characterized by the high resolution H-1, C-13, H-1-H-1 COSY and H-1-C-13 COSY spectra. Spectral data indicate the trans arrangement of the side chain protons H(3), H(4) and H(5) and trans orientation of H(3) proton with respect to cyano group in 1-9. Computational calculations were carried out for some possible structures and they support the conformation in which all side chain protons are trans to each other and H(3) proton is trans to CN group. Moreover, syn orientation of NO2 group with respect to H(5) proton in 4-6 is revealed by computational calculations and chemical shift data. From the favored conformations, geometrical parameters, HOMO-LUMO energies, dipole moment, polarizabilities and first order hyperpolarizabilities were determined theoretically. The highest beta(tot) is observed for the nitrile 9 where electron releasing substituent (OCH3) and electron withdrawing substituent (NO2) are present at the opposite ends of the conjugated system and hence it is the best NLO candidate. The NLO character decreases according to the order 9 > 3 > 5 > 4 > 7 > 8 > 6 > 2 > 1. The H-1 and C-13 chemical shifts in gaseous state as well as in solution were also determined theoretically by DFT method and they are in agreement with the experimental values. NBO analyses were further carried out for the minimum energy conformer. From H-1 and C-13 chemical shifts, the effect of introduction of substituents (NO2, OCH3, Cl) in the phenyl ring on the chemical shifts of the side chain protons [H(3), H(4) and H(5)] and carbons [C(3), C(4) and C(5)] were analyzed in detail. (C) 2011 Elsevier B.V. All rights reserved.