4-[(2-methoxyphenyl)diazenyl]-5-methyl-1H-pyrazol-3-amine | 947731-79-5

• 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: 4-[(2-methoxyphenyl)diazenyl]-5-methyl-1H-pyrazol-3-amine
• CAS: 947731-79-5
• 化学式: C₁₁H₁₃N₅O
• 分子量: 231.257
• InChiKey: WMCKPFQHSQKGQD-UHFFFAOYSA-N

物化性质

• 沸点：
  511.3±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(2-methoxyphenyl)diazenyl]-5-methyl-1H-pyrazol-3-amine 在 亚硝基硫酸 、 溶剂黄146 作用下， 反应 8.0h， 生成 C₁₆H₁₇N₇O₃
  参考文献：
  名称：

  吡唑并[5,1-c] [1,2,4]三嗪类分散染料的合成和吸收能力

  摘要：

  通过在冰醋酸中加热吡唑基肼基氰基氰基乙酸乙酯，合成了13种新颖的吡唑并[5,1- c ] [1,2,4]三嗪基分散染料。研究了溶剂和酸碱对最大吸收波长的影响。

  DOI：

  10.1007/s10593-013-1268-3
• 作为产物：
  描述：

  邻甲氧基苯胺 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 4-[(2-methoxyphenyl)diazenyl]-5-methyl-1H-pyrazol-3-amine
  参考文献：
  名称：

  新型2,4-二羟基喹啉染料的抗癌，抗菌和DNA保护分析

  摘要：

  通过5-氨基-4-苯基偶氮-3-甲基-1H-吡唑衍生物与2,4-二羟基喹啉的反应合成了一系列新的2,4-二羟基喹啉衍生的二偶氮染料。通过各种分光光度法，例如FT-IR，1 H-NMR和元素分析来鉴定获得的染料的结构。还检查了合成的化合物的不同生物活性，包括DNA保护，抗微生物和抗癌活性。发现化合物3b对革兰氏阳性细菌最有效。对所有化合物都进行了DNA保护分析，发现化合物3h和3j具有与DNA结合的高能力。此外，化合物3h和3j对HeLa和PC3癌细胞系显示出细胞毒性。基于它们对细菌和癌细胞系的作用，这些化合物有可能被用作药物或药物添加剂。

  DOI：

  10.1016/j.dyepig.2018.04.040

文献信息

• Synthesis of some new pyrazolo[5,1-c][1,2,4]triazine derivatives and computational study
  作者：Fati Yıldırım、Aykut Demirçalı、Aslı Öztürk Kiraz、Fikret Karcı

  DOI：10.1016/j.molstruc.2020.128850

  日期：2020.12

  Abstract In this study, the synthesis novel of seven new pyrazolo [5,1-c][1,2,4]triazin derivative disperse dyestuffs was reported. First, 2-arylhydrazone-3-ketiminobutyronitriles were synthesized and reacted with hydrazine hydrate to afford 5-amino-4-arylazo-3-methyl-1H-pyrazoles. The 5-amino-4-arylazo-3-methyl-1H-pyrazoles were diazotised and coupled with ethyl benzoylacetate to give ethyl pyrazolylazo

  摘要 本研究报道了七种新型吡唑并[5,1-c][1,2,4]三嗪衍生物分散染料的合成新进展。首先，合成2-芳基腙-3-酮亚氨基丁腈并与水合肼反应得到5-氨基-4-芳基偶氮-3-甲基-1H-吡唑。将 5-氨基-4-芳基偶氮-3-甲基-1H-吡唑重氮化并与苯甲酰乙酸乙酯偶联，得到吡唑基偶氮苯甲酰乙酸乙酯。最终产物在冰醋酸中加热，合成了七种新型吡唑并[5,1-c][1,2,4]三嗪染料。FT-IR、1H NMR 和元素分析技术用于表征合成染料。密度泛函理论计算方法被用于确定新七种染料的分子几何形状和光谱特性。
• New coumarin-based disperse disazo dyes: Synthesis, spectroscopic properties and theoretical calculations
  作者：Fati Yıldırım、Aykut Demirçalı、Fikret Karcı、Alpaslan Bayrakdar、Pınar Tunay Taşlı、H.Hüseyin Kart

  DOI：10.1016/j.molliq.2016.08.008

  日期：2016.11

  razoles (3a-l) have been diazotised and coupled with 4-hydroxycoumarin to give rise to the coumarin-based disperse disazo dyes (3a-l). The newly synthesized twelve coumarin-based disperse disazo dyes have been characterized by using the elemental analysis and the spectral methods. The solvatochromic behavior of these dyes in various solvents is evaluated. Substituent, acid and base effects on the visible

  已经将5-氨基-4-芳基偶氮-3-甲基-1H-吡唑（3a - 1）重氮化并与4-羟基香豆素偶联以产生基于香豆素的分散二偶氮染料（3a - 1）。通过元素分析和光谱方法对新合成的十二种香豆素基分散型二偶氮染料进行了表征。评估了这些染料在各种溶剂中的溶剂变色行为。取代基，酸和碱对在o-，m-和p处被吸电子和供电子基团取代的染料的可见吸收光谱的影响-位置也有详细报道。还使用基态下基于密度泛函理论（DFT）的从头算方法，对本文中考虑的化合物的分子几何结构和光谱性质进行了分析。从DFT获得的理论结果与实验结果相符。
• Disazo dyes containing pyrazole and indole moieties: Synthesis, characterization, absorption characteristics, theoretical calculations, structural and electronic properties
  作者：Çiğdem Karabacak Atay、Yeşim Kara、Merve Gökalp、Izzet Kara、Tahir Tilki、Fikret Karci

  DOI：10.1016/j.molliq.2016.01.031

  日期：2016.3

  recorded and chemical shifts of the molecules were compared to TMS by using the Gauge-Independent Atomic Orbital (GIAO) method. A study on the electronic and optical properties, absorption wavelengths, excitation energy and dipole moment is performed using DFT method. NBO analysis is carried out to picture the charge transfer between the localized bonds and lone pairs. All spectroscopic properties examined

  通过5-氨基-4-芳基偶氮-3-甲基-1H-吡唑2a-2m的重氮化并与2-甲基吲哚偶联制备了新合成的十三种分散二偶氮染料3a-3m。通过紫外可见光谱，傅立叶变换红外光谱，1 H NMR和元素分析对它们的结构进行了表征。研究了在不同溶剂中的溶剂变色性质。此外，还告知了酸和碱对染料可见吸收光谱的影响。此外，理论振动频率已经定标，并与相应的实验数据进行了比较。1个记录1 H NMR光谱，并使用不依赖于量规的原子轨道（GIAO）方法将分子的化学位移与TMS进行比较。使用DFT方法对电子和光学性质，吸收波长，激发能和偶极矩进行了研究。进行NBO分析以描绘局部键和孤对之间的电荷转移。计算结果支持了用实验技术检查的所有光谱特性。
• The synthesis, spectroscopic properties and theoretical calculation of some novel disperse disazo dyes derived from 3-amino-5-hydroxy-1-phenylpyrazole
  作者：Fati Karcı、Aykut Demirçalı、Fikret Karcı、İzzet Kara、Fatih Ucun

  DOI：10.1016/j.molstruc.2009.06.040

  日期：2009.10

  In this study 5-amino-4-arylazo-3-methyl-1H-pyrazoles (1a-1m) were diazotised and coupled with 3amino-5-hydroxy-1-phenylpyrazole to give disperse disazo dyes (2a-2m). The newly synthesized 13 disperse disazo dyes were characterized by elemental analysis and spectral methods. The solvatochromic behaviour of these disperse disazo dyes in various solvents was evaluated. Substituent, acid and base effects on the visible absorption spectra of the disperse disazo dyes substituted with electron-withdrawing and electron-donating groups at their o-, m-, p-position were also reported in detail. Additionally, theoretical calculations are performed for the disazo dyes. The molecular geometry and chemical shift are calculated by using ab initio calculations based on the density functional theory (DFT) in the ground state. The results obtained are in agreement with the experimental results. (C) 2009 Elsevier B.V. All rights reserved.
• Synthesis, solvatochromic properties and antimicrobial activities of some novel pyridone-based disperse disazo dyes
  作者：Fati Karcı、Fikret Karcı、Aykut Demirçalı、Mustafa Yamaç

  DOI：10.1016/j.molliq.2013.08.005

  日期：2013.11

  In this study, 5-amino-4-arylazo-3-methyl-1H-pyrazoles (2a-1) were diazotized and coupled with 3-cyano-6-hydroxy-4-methyl-2-pyridone to give pyridone-based disperse disazo dyes (3a-1). The newly synthesized twelve pyridone-based disperse disazo dyes were characterized by elemental analysis and spectral methods. The solvatochromic properties and antimicrobial activities of these disazo disperse dyes were also examined in detail. (C) 2013 Elsevier B.V. All rights reserved.