5-(cyclohexylamino)-2-(4-methoxyphenyl)-2H-1,2,3-triazole-4-carbonitrile | 1088707-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(cyclohexylamino)-2-(4-methoxyphenyl)-2H-1,2,3-triazole-4-carbonitrile
• 英文别名: 5-(Cyclohexylamino)-2-(4-methoxyphenyl)triazole-4-carbonitrile；5-(cyclohexylamino)-2-(4-methoxyphenyl)triazole-4-carbonitrile
• CAS: 1088707-48-5
• 化学式: C₁₆H₁₉N₅O
• 分子量: 297.36
• InChiKey: GXPUIBDEUCBFKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(cyclohexylamino)-2-(4-methoxyphenyl)-2H-1,2,3-triazole-4-carbonitrile 在 吡啶 、 硫化氢 、 三乙胺 作用下， 以94%的产率得到5-cyclohexylamino-2-(4-methoxyphenyl)-2H-1,2,3-triazole-4-thiocarboxamide
  参考文献：
  名称：

  Synthesis and reactions of thioamides of 5-amino-2-aryl-2H-1,2,3-triazole-4-carboxylic acid

  摘要：

  A method has been developed for obtaining thioamides of 5-amino-2-aryl-2H-1,2,3-triazole-4-carboxylic acid. Their heterocyclization reactions with bifunctional reagents has been studied. New heterocyclic polycyclic ensembles have been synthesized containing a 1,2,3-triazole fragment, a thiazole, and a residue of the natural alkaloid cytisine.

  DOI：

  10.1007/s10593-009-0348-x
• 作为产物：
  描述：

  在 copper(II) acetate monohydrate 作用下， 反应 6.0h， 以180 mg的产率得到5-(cyclohexylamino)-2-(4-methoxyphenyl)-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

文献信息

• 5-Amino-2-aryl-1,2,3-triazol-4-carboxylic acids: Synthesis, photophysical properties, and application prospects
  作者：Nikita E. Safronov、Timur O. Fomin、Artem S. Minin、Lozan Todorov、Irena Kostova、Enrico Benassi、Nataliya P. Belskaya

  DOI：10.1016/j.dyepig.2020.108343

  日期：2020.7

  present an effective strategy for the synthesis of novel 2-aryl-1,2,3-triazol-4-carboxylic acids (ATAs). The behavior of ATAs in different solvents showed that these new 1,2,3-triazole derivatives had bright blue fluorescence with excellent quantum yields, large Stokes shifts, and prolonged fluorescence lifetimes. Their photophysical and physicochemical properties showed extra sensitivity to both structural

  为了扩大小分子杂环的高活性荧光团家族，我们提出了一种新型2-芳基-1,2,3-三唑-4-羧酸（ATAs）合成的有效策略。ATA在不同溶剂中的行为表明，这些新的1,2,3-三唑衍生物具有明亮的蓝色荧光，具有出色的量子产率，大的斯托克斯位移和延长的荧光寿命。它们的光物理和理化性质对结构变化和微环境都表现出额外的敏感性，通常伴随着量子产率的显着变化。ATA对不同pH的响应取决于三唑环C5原子上氨基的结构。对于带有叔氨基的ATA，pKa值为7.65–8.08。相反，带有仲烷基胺的ATA的pKa值在3.20-3.52之间。量子力学方法被用来理解潜在的转变并解释获得的实验数据。在合成的化合物中，观察到聚集诱导的发射增强（AIEE）行为，具有潜在的应用作为监测和控制pH值的传感器。ATA在酸性和碱性pH值之间的可逆性及其毒性支持其在生物学研究中的实时使用。具有潜在的应用作为监测和控制pH值的传感器。AT
• 5-Amino-2-aryl-2H-1,2,3-triazole-4-carboxamides: Unique AIEE-gens and selective Hg2+ fluorosensors
  作者：Nikita E. Safronov、Artem S. Minin、Pavel A. Slepukhin、Irena P. Kostova、Enrico Benassi、Nataliya P. Belskaya

  DOI：10.1016/j.saa.2023.122419

  日期：2023.5

  any appreciable changes in fluorescence intensity. The CATs form a complex with Hg2+ with highly specific detection for Hg2+ over other competitive metal ions: the detection limits were determined to be 0.23 and 0.15 μM for the CATs 1b and 2c. The reverse effect was registered with the addition of ethylene diamine sodium salt; meanwhile, the CATs demonstrated more effective coordination with Hg2+ in comparison

  设计并充分表征了一系列基于小分子的荧光传感器，证明了 AIEE 效应并揭示了选择性检测 Hg 2+离子的出色能力。 通过（时间相关）密度泛函理论（（TD）-DFT）水平的量子化学计算研究了结构和电子特性。2-Aryl-1,2,3-Triazoles (CAT) 的甲酰胺在其光物理性质上表现出显着差异，具体取决于杂环中 C5 原子上氨基功能取代基的结构。当连接叔环烷基氨基（吡咯烷、哌啶、氮杂环庚烷）时，三唑显示出高强度蓝色荧光，在不同溶剂中的量子产率 (QY) 高达 95%，寿命高达 6.9 ns，而同系物的 QY 具有仲烷基氨基（即NHMe、NHC 6 H 11 -环) 表示低 QY (1-10%)。尽管如此，所获得的所有类型的荧光团都表现出优异的 AIEE 效应，并在有机溶剂和水的二元混合物中形成荧光纳米粒子。甲酰胺功能的引入增强了 2-aryl-1,2,3-triazole 的传感特性，在