Propanedinitrile, [[2-(trifluoromethyl)phenyl]hydrazono]- | 101398-31-6

• 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: Propanedinitrile, [[2-(trifluoromethyl)phenyl]hydrazono]-
• 英文别名: 2-[[2-(trifluoromethyl)phenyl]hydrazinylidene]propanedinitrile
• CAS: 101398-31-6
• 化学式: C₁₀H₅F₃N₄
• mdl: MFCD00042196
• 分子量: 238.172
• InChiKey: LMFPADXPOKBSAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  Propanedinitrile, [[2-(trifluoromethyl)phenyl]hydrazono]- 在 copper(II) acetate monohydrate 作用下， 以 乙腈 为溶剂， 反应 50.17h， 生成 5-(pyrrolidin-1-yl)-2-(2-(trifluoromethyl)phenyl)-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：

  丙二腈 、 邻氨基三氟甲苯 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 为溶剂， 反应 1.5h， 生成 Propanedinitrile, [[2-(trifluoromethyl)phenyl]hydrazono]-
  参考文献：
  名称：

  4-arylazo-3,5-diamino-1H-pyrazoles 的 SAR 研究：鉴定诱导铜绿假单胞菌生物膜分散的小分子

  摘要：

  通过筛选 50 000 种小分子化合物的集合，我们最近将 4-arylazo-3,5-diamino-1 H -pyrazoles 鉴定为一组新型抗生物膜剂。在这里，我们报告了一项基于 60 种类似物的 SAR 研究，通过检查可以进一步优化药效团的方法，例如通过芳环中的取代。SAR 研究揭示了非常有效的抗生物膜化合物 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1 H -pyrazol-3-amine ( 2 )。

  DOI：

  10.1039/d1md00275a

文献信息

• Sturdik, Ernest; Durcova, Edita; Mikes, Vladimir, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 11, p. 2819 - 2825
  作者：Sturdik, Ernest、Durcova, Edita、Mikes, Vladimir、Dadak, Vladimir、Balaz, Stefan、et al.

  DOI：——

  日期：——
• SAR study of 4-arylazo-3,5-diamino-1<i>H</i>-pyrazoles: identification of small molecules that induce dispersal of <i>Pseudomonas aeruginosa</i> biofilms
  作者：Charlotte U. Jansen、Jesper Uhd、Jens B. Andersen、Louise D. Hultqvist、Tim H. Jakobsen、Martin Nilsson、Thomas E. Nielsen、Michael Givskov、Tim Tolker-Nielsen、Katrine M. Qvortrup

  DOI：10.1039/d1md00275a

  日期：——

  4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of anti-biofilm agents. Here, we report a SAR study based on 60 analogues by examining ways in which the pharmacophore can be further optimized, for example, via substitutions in the aryl ring. The SAR study revealed the very potent anti-biofilm compound 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1H-pyrazol-3-amine (2).

  通过筛选 50 000 种小分子化合物的集合，我们最近将 4-arylazo-3,5-diamino-1 H -pyrazoles 鉴定为一组新型抗生物膜剂。在这里，我们报告了一项基于 60 种类似物的 SAR 研究，通过检查可以进一步优化药效团的方法，例如通过芳环中的取代。SAR 研究揭示了非常有效的抗生物膜化合物 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1 H -pyrazol-3-amine ( 2 )。
• 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.