2-(3-cyano-4-(4-((2-hydroxyethyl)(methyl)amino)styryl)-5,5-dimethylfluran-2(5H)-ylidene)malononitrile | 916674-81-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(3-cyano-4-(4-((2-hydroxyethyl)(methyl)amino)styryl)-5,5-dimethylfluran-2(5H)-ylidene)malononitrile
• 英文别名: 2-{3-cyano-4-[((2-hydroxyethyl)(methyl)amino)styryl]-5,5-dimethylfuran-2(5H)-ylidene}malononitrile；2-(3-Cyano-4-(4-((2-hydroxyethyl)(methyl)amino)styryl)-5,5-dimethylfuran-2(5h)-ylidene)malononitrile；2-[3-cyano-4-[2-[4-[2-hydroxyethyl(methyl)amino]phenyl]ethenyl]-5,5-dimethylfuran-2-ylidene]propanedinitrile
• CAS: 916674-81-2
• 化学式: C₂₁H₂₀N₄O₂
• 分子量: 360.415
• InChiKey: JMDHDDFDSCMMIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104.07
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  丁二酸酐 、 2-(3-cyano-4-(4-((2-hydroxyethyl)(methyl)amino)styryl)-5,5-dimethylfluran-2(5H)-ylidene)malononitrile 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到4-(2-((4-(2-(4-cyano-5-(dicyanomethylene)-2,2-dimethyl-2,5-dihydrofuran-3-yl)vinyl)phenyl)(methyl)amino)ethoxy)-4-oxobutanoic acid
  参考文献：
  名称：

  基于3-苯氧基丙烷-1，2-二醇的双发色团，可增强非线性光学性能

  摘要：

  通过元素分析，紫外-可见吸收光谱和1 H NMR证实了一种新型的双色团的结构，该结构包括一个可通过酯化作用与3-苯氧基丙烷-1，2-二醇形成的超极化性发色团。通过将双色团和相应的单色团掺杂到聚（4-乙烯基苯酚）中来制备非线性光学聚合物膜。原位二次谐波生成测量结果表明，双发色团使薄膜的二次谐波生成系数提高了2.2倍，表明新型3-苯氧基丙烷-1，2-二醇衍生物可用于多酚的设计和合成-发色树状大分子，具有大的宏观光学非线性。

  DOI：

  10.1016/j.dyepig.2010.03.027
• 作为产物：
  描述：

  2-dicyanomethylene-3-cyano-4-methyl-2,5-dihydrofuran 、 N-甲基-N-(2-羟乙基)-4-氨基苯醛 以 乙醇 为溶剂， 反应 2.0h， 生成 2-(3-cyano-4-(4-((2-hydroxyethyl)(methyl)amino)styryl)-5,5-dimethylfluran-2(5H)-ylidene)malononitrile
  参考文献：
  名称：

  铜（I）催化的点击反应合成的两个新型双色团的增强的电光活性

  摘要：

  本文通过Cu（I）催化的点击反应合成了基于传统苯胺生色团YL的两个新型双生色团YL1和YL2，并对其进行了系统的研究。对这些生色团的UV-Vis，电化学性质，热稳定性和EO活性进行了系统的研究和讨论。这两个双色团显示出良好的热稳定性。然后通过将发色团掺杂到聚甲基丙烯酸甲酯（PMMA）中来制造非线性光学聚合物膜。含双色团YL1和YL2的掺杂薄膜在1310 nm处浓度为25 wt％时，r 33值为20和17 pm / V。这些值分别是发色团YL（7 pm / V）的EO活性的2.85倍和2.43倍。高r 33值表明，双色团YL1和YL2的新结构可以减少分子间静电相互作用，从而增强宏观EO活性。这些性质表明，新的双色团在非线性光学材料中的潜在用途。

  DOI：

  10.1016/j.dyepig.2017.01.009

文献信息

• Preparation of polymer films containing multi-branched chromophores for enhanced nonlinear optical activity
  作者：Wenxin Lin、Yuanjing Cui、Jiancan Yu、Yu Yang、Guodong Qian

  DOI：10.1016/j.dyepig.2016.09.040

  日期：2017.1

  Two new multi-branched chromophores were synthesized via esterification from monochromophores to achieve ideal macroscopic nonlinear optical activities. Molecular chemical structures of chromophores were confirmed by 1H NMR, FT-IR spectroscopy, elemental analysis, mass spectrometry and UV–visible absorption spectra. Monochromophore N1 and bichromophore DN were doped into poly (4-vinylphenol) to fabricate

  通过酯化反应从单色团合成了两个新的多支化色团，以实现理想的宏观非线性光学活性。发色团的分子化学结构通过1 H NMR，FT-IR光谱，元素分析，质谱和UV-可见吸收光谱确定。将单发色团N1和双发色团DN掺杂到聚（4-乙烯基苯酚）中，以制备具有高分子负载密度（最高30 wt％）的客体-主体聚合物膜Film-N1和Film-DN。聚合物膜Film-N1和Film-DN的最大二次谐波产生系数（d 33）达到25 pm V-1和39 pm V -1。与此相反，六支树突生色SN直接用于制备薄膜膜-SN没有任何聚合物基质由于其分子量大（约3183道尔顿）和d 33的值电影-SN达208分V - 1。与Film-N1相比，含有多支发色团Film-DN和Film-SN的薄膜在d 33中显示出约1.6倍和8.3倍的增强 表示多支发色团的值可以通过位点隔离效应显着促进宏观光学非线性。
• Synthesis and property of solvatochromic fluorophore based on D-π-A molecular system: 2-{[3-Cyano-4-(N-ethyl-N-(2-hydroxyethyl)amino)styryl]-5,5-dimethylfuran-2(5H)-ylidene}malononitrile dye
  作者：Young-A Son、Seon-Yeong Gwon、Sue-Yoen Lee、Sung-Hoon Kim

  DOI：10.1016/j.saa.2009.10.015

  日期：2010.1

  2-[3-Cyano-4-(N-ethyl-N-(2-hydroxyethyl)amino)styryl]-5,5-dimethylfuran-2(5H)-ylidene}malono nitrile styryl dye was prepared by the condensation of 4-[(2-hydroxy-ethyl)-methyl-amino]-benzaldehyde (donor moiety) with 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (acceptor moiety). The corresponding design, synthesis and solvatochromic characteristics of the intramolecular charge-transfer (ICT) dye chromophore were discussed and determined. Optical properties Such as absorption and fluorescence emission spectra were monitored in several solvent media with different polarity. In this determination, the prepared dye chromophore showed positive solvatochromisrn effect and the resulting solvatochromic characteristics were Studied with semiempirical calculations. The energy potentials of this dye chromophore such as HOMO and LUMO values were calculated by computational simulation approaches using Material Studio 4.3. Furthermore, the functions as a molecular switching sensor with pH stimulation of alkali-acid addition were determined in DMSO, which was operated by deprotonation/protonation effects based on intramolecular charge-transfer system. (C) 2009 Elsevier B.V. All rights reserved.