2-[2-(4-cyanophenyl)hydrazono]malononitrile | 64691-81-2

• 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: 2-[2-(4-cyanophenyl)hydrazono]malononitrile
• 英文别名: Propanedinitrile, ((4-cyanophenyl)hydrazono)-；2-[(4-cyanophenyl)hydrazinylidene]propanedinitrile
• CAS: 64691-81-2
• 化学式: C₁₀H₅N₅
• mdl: MFCD01698284
• 分子量: 195.183
• InChiKey: FMYMDEPLLXDYGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2-(4-cyanophenyl)hydrazono]malononitrile 在 copper(II) acetate monohydrate 作用下， 以 乙腈 为溶剂， 反应 15.17h， 生成 2-(4-cyanophenyl)-5-(pyrrolidin-1-yl)-2H-1,2,3-triazole-4-carbonitrile
  参考文献：
  名称：

  2-Aryl-5-amino-1,2,3-triazoles: New effective blue-emitting fluorophores

  摘要：

  The synthesis of a new series of 2-aryl-5-amino-1,2,3-triazole derivatives is reported. The photochemical properties of these new fluorophores were studied both experimentally and using theoretical models. The compounds were found to be fluorescent, with Stokes shifts ranging from 40 nm (2494 CM-1) to 140 nm (9461 cm(-1)) and quantum yield values between 0.004 and 0.996. The fluorescence of the 1,2,3-triazoles was highly structure dependent and could be tuned by variation of the substituents at the C-4 and C-5 atoms of triazole ring and by the electronic and spatial effect of substituents within the aromatic cycle. Photophysical studies showed moderate changes in the fluorescence quantum yields depending on the solvent polarity. The UV-Vis spectra calculations employing the time-dependent density functional theory (TD-DFT) are in good agreement with the experimental data. The favourable photophysical properties of the studied compounds and their facile and high-yielding synthesis make them excellent candidates for commercial application as fluorescent tags. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.08.015
• 作为产物：
  描述：

  4-氰基重氮苯四氟硼酸盐 、 丙二腈 在 sodium acetate 、 silica gel 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以92%的产率得到2-[2-(4-cyanophenyl)hydrazono]malononitrile
  参考文献：
  名称：

  高速球磨机械活化的苯并hydr衍生物的固态合成

  摘要：

  在高速球磨条件下，由四氟硼酸壬二唑鎓盐和活性亚甲基化合物合成了一系列苯hydr衍生物。该反应在不存在溶剂的情况下发生，并且在短反应时间内（不超过30分钟）以良好的产率获得了产物。

  DOI：

  10.2174/1570178611999140404111411

文献信息

• Synthesis of arylhydrazone-based molecular switches using aryldiazonium silica sulfate nanocomposites and analysis of their isomerization
  作者：Amin Zarei、Leila Khazdooz、Solmaz Soltani、Alireza Najafi Chermahini、Hamidreza Aghaei、Alireza Abbaspourrad

  DOI：10.1016/j.dyepig.2021.109544

  日期：2021.10

  each synthesized compound in these two solvents. By changing the solvent from CHCl3 to DMSO, the E/Z ratios decreased. The results demonstrated that the ΔG° values for the formation of Z isomers were more negative than those of the E isomers in DMSO. This is why Z isomers are more stable than E isomers in DMSO. The results of density functional theory (DFT) calculations at B3LYP/6–311++G (d,p) level

  报道了一种通过芳基重氮硅硫酸盐纳米复合材料与丙二腈、乙酰乙酸乙酯和二甲酮反应来合成一系列芳基腙的快速有效方法。所有反应均在室温下在水中进行，相应的产物以 77-87% 的产率获得。使用乙酰乙酸乙酯合成的芳基腙中存在两种分子内氢键，使这些化合物能够通过围绕腙C N 键旋转而转换，从而导致它们的E和Z构型之间的可逆异构化。这种转换可以通过改变溶剂的极性来控制。在 CHCl 3 中研究了每种合成化合物的E/Z比和二甲基亚砜。E/Z的比率是使用1 H NMR 数据在 CDCl 3和 DMSO- d 6中计算的，并用于计算每种合成化合物在这两种溶剂中的EZ异构化的ΔG ° 。通过将溶剂从 CHCl 3改为 DMSO，E/Z比降低。结果表明，在 DMSO 中形成Z异构体的 Δ G ° 值比E异构体的更负。这就是为什么Z异构体比E更稳定DMSO 中的异构体。B3LYP/6–311++G (d,p) 理论水平的密度泛函理论
• Effect of new carbonyl cyanide aromatic hydrazones on biofilm inhibition against methicillin resistant <i>Staphylococcus aureus</i>
  作者：Xueer Lu、Ziwen Zhang、Yingying Xu、Jun Lu、Wenjian Tang、Jing Zhang

  DOI：10.1039/d0ra03124k

  日期：——

  and 1.56 μM, respectively). Some compounds in combination with antibiotics exhibited potentiate Gram-positive antibacterial activity; compound 2e was found to display unaided or synergistic efficacy against MRSA. In particular, when compound 2e is combined with ofloxacin, it has a good synergistic effect against MRSA. Moreover, electron microscopy revealed that compound 2e inhibits biofilm formation

  羰基氰化物间氯苯腙 (CCCP) 作为一种质子载体，与抗生素结合表现出增强的抗菌活性。为了提高CCCP的效力和毒性，合成了一系列芳香腙，并对其抗菌活性进行了评价；其中，化合物2e和2j在苯环上具有强对位吸电子取代基（-NO 2和-CF 3 ），对金黄色葡萄球菌和耐甲氧西林金黄色葡萄球菌的 MIC 最低（分别为 1.56 和 1.56 μM）。一些化合物与抗生素组合表现出增强的革兰氏阳性抗菌活性；发现化合物2e对 MRSA 表现出单独的或协同的功效。特别是化合物2e与氧氟沙星合用时，对MRSA具有良好的协同作用。此外，电子显微镜显示化合物2e抑制生物膜形成并有效根除预先形成的生物膜。MTT 分析表明，化合物2e的毒性与 CCCP 一样低。总体而言，我们的数据表明，芳香腙是一种很有前途的抗葡萄球菌药物开发支架。
• “Clip-cycle” synthesis of 2-pyridazinones bearing enaminonitrile moiety from thioesters and dicyanohydrazones
  作者：Chen Zhu、Jubao Zhou、Xinxin Li、Xinyu Wang、Hui Jin、Lixin Zhang

  DOI：10.1016/j.tetlet.2023.154905

  日期：2024.1

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  [显示省略]
• 2-Aryl-5-amino-1,2,3-triazoles: New effective blue-emitting fluorophores
  作者：Kseniya D. Gavlik、Ekaterina S. Sukhorukova、Yuri M. Shafran、Pavel A. Slepukhin、Enrico Benassi、Nataliya P. Belskaya

  DOI：10.1016/j.dyepig.2016.08.015

  日期：2017.1

  The synthesis of a new series of 2-aryl-5-amino-1,2,3-triazole derivatives is reported. The photochemical properties of these new fluorophores were studied both experimentally and using theoretical models. The compounds were found to be fluorescent, with Stokes shifts ranging from 40 nm (2494 CM-1) to 140 nm (9461 cm(-1)) and quantum yield values between 0.004 and 0.996. The fluorescence of the 1,2,3-triazoles was highly structure dependent and could be tuned by variation of the substituents at the C-4 and C-5 atoms of triazole ring and by the electronic and spatial effect of substituents within the aromatic cycle. Photophysical studies showed moderate changes in the fluorescence quantum yields depending on the solvent polarity. The UV-Vis spectra calculations employing the time-dependent density functional theory (TD-DFT) are in good agreement with the experimental data. The favourable photophysical properties of the studied compounds and their facile and high-yielding synthesis make them excellent candidates for commercial application as fluorescent tags. (C) 2016 Elsevier Ltd. All rights reserved.
• Mechanically Activated Solid-State Synthesis of Phenylhydrazone Derivatives via High-Speed Ball Milling
  作者：Xingyi Zhu、Yuanyuan Chen、Yuhe Chen、Jue Wang、Weike Su

  DOI：10.2174/1570178611999140404111411

  日期：2014.6

  A series of phenylhydrazone derivatives was synthesized from arenediazonium tetrafluoroborates and active methylene compounds under high-speed ball milling. The reaction occurred in the absence of the solvent and products were obtained in good yield within short reaction times (no more than 30 min).

  在高速球磨条件下，由四氟硼酸壬二唑鎓盐和活性亚甲基化合物合成了一系列苯hydr衍生物。该反应在不存在溶剂的情况下发生，并且在短反应时间内（不超过30分钟）以良好的产率获得了产物。