4-((4-nitrophenyl)diazenyl)-1H pyrazole-3,5-diamine | 62679-04-3

• 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-((4-nitrophenyl)diazenyl)-1H pyrazole-3,5-diamine
• 英文别名: 4-(4-Nitrophenylazo)-1H-pyrazole-3,5-diamine；4-[(4-nitrophenyl)diazenyl]-1H-pyrazole-3,5-diamine
• CAS: 62679-04-3
• 化学式: C₉H₉N₇O₂
• 分子量: 247.216
• InChiKey: WGDRKGIORBVJCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-((4-nitrophenyl)diazenyl)-1H pyrazole-3,5-diamine 在 哌啶 作用下， 反应 3.5h， 生成 8-(4-nitro-phenylazo)-N⁴-phenyl-pyrazolo[1,5-a][1,3,5]triazine-2,4,7-triamine
  参考文献：
  名称：

  Elgemeie; Sood, Journal of Chemical Research - Part S, 2001, # 10, p. 439 - 441

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基氯化重氮苯 在 吡啶 、 sodium ethanolate 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 4-((4-nitrophenyl)diazenyl)-1H pyrazole-3,5-diamine
  参考文献：
  名称：

  Fluoride-responsive organogel containing azobenzyl and cholesterol units

  摘要：

  In this paper, two new cholesterol-based compounds 01 and 02 were designed and synthesized. The compound 02 could selectively gel in 1,4-dioxane with porous ribbon structure. The aggregation mode of 02 molecules were characterized by SEM, IR, UV-vis and XRD experiments. Interestingly, the gel of 02 was also fluoride-responsive. The addition of TBAF on the gel surface would trigger the gel-sol transition, and the collapse time could be controlled by amount of fluoride ions. The response process was also accompanied by dramatic color changes from orange to purple. From the NMR titration experiments, it was deduced that the hydrogen bonding competition between the anion-receptor and self-assembly of the receptor played an important role for the gel-sol transition. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.12.005

文献信息

• Synthesis, Absorption Properties and Biological Evaluation of Some Novel Disazo Dyes Derived from Pyrazole Derivatives
  作者：Nesrin Sener、Izzet Sener、Serkan Yavuz、Fikret Karci

  DOI：10.14233/ajchem.2015.18769

  日期：——

  In this study, 20 novel disazo dyes containing pyrazole derivatives were synthesized by a convenient method. Diazotized aniline and some aniline derivatives were reacted with malononitrile to give 2-arylazomalononitrile derivatives 1(a-e). The synthesized 2-arylazomalononitrile derivatives were reacted with hydrazine and phenyl hydrazine to afford the corresponding 3,5-diamino-4-arylazo-1H-pyrazole 2(a-e) and 3,5-diamino-4-arylazo-1-phenylpyrazole 3(a-e). Diazotized compounds of 2(a-e)and 3(a-e) reacted with ethylacetoacetate to give 4-arylazo-3-amino-1H-pyrazole-5-ylazo-ethylacetoacetate 4(a-e) and 4-arylazo-3-amino-1-phenylpyrazole-5-ylazo-ethylacetoacetate 7(a-e). The obtained 4(a-e) and 7(a-e) were reacted with hydrazine and phenyl hydrazine to give disazo dyes 5(a-e), 6(a-e), 8(a-e) and 9(a-e), respectively. The synthesized disazo dyes were characterized by spectroscopic techniques as well as elemental analysis. The solvatochromic behaviours of these dyes in various solvents were examined. Acid-base effects on the absorption maxima of the dyes were also reported. Antimicrobial activities of the synthesized novel disazo dyes were investigated.

  在本研究中，通过一种简便的方法合成了20种含吡唑衍生物的新型双偶氮染料。重氮化的苯胺及一些苯胺衍生物与丙二腈反应得到2-芳基偶氮丙二腈衍生物1(a-e)。合成的2-芳基偶氮丙二腈衍生物与肼和苯肼反应，分别得到相应的3,5-二氨基-4-芳基偶氮-1H-吡唑2(a-e)和3,5-二氨基-4-芳基偶氮-1-苯基吡唑3(a-e)。2(a-e)和3(a-e)的重氮化合物与乙酰乙酸乙酯反应得到4-芳基偶氮-3-氨基-1H-吡唑-5-偶氮-乙酰乙酸乙酯4(a-e)和4-芳基偶氮-3-氨基-1-苯基吡唑-5-偶氮-乙酰乙酸乙酯7(a-e)。所得的4(a-e)和7(a-e)分别与肼和苯肼反应，得到双偶氮染料5(a-e)、6(a-e)、8(a-e)和9(a-e)。合成的双偶氮染料通过光谱技术和元素分析进行表征。这些染料在不同溶剂中的溶剂化变色行为被研究。酸碱效应对染料最大吸收的影响也被报道。合成的双偶氮染料的抗菌活性也被研究。
• Novel heterocyclic disazo dyes containing pyrazole and phenylpyrazole. part 1: Synthesis, characterization, solvent polarity and acid-base sensitive characteristics
  作者：Aykut Demirçalı

  DOI：10.1016/j.molstruc.2021.129960

  日期：2021.5

  A series of diazotised aniline and aniline derivative compounds were reacted with solution of malononitrile in pyridine at 0–5 °C were obtained 1a-1m compounds. Then 4-arylazo-3,5-diamino-1H-pyrazole (2a-2m) derivatives were synthesized by coupling arylazo malononitrile compounds with hydrazine. Finally, the synthesized pyrazole derivative 2a-2m compounds were again diazotised. By reacting these diazotised

  在0〜5℃下，将一系列重氮化的苯胺和苯胺衍生物与丙二腈在吡啶中的溶液反应，得到1a-1m的化合物。然后通过将芳基偶氮丙二腈化合物与肼偶合来合成4-芳基偶氮-3，5-二氨基-1H-吡唑（2a-2m）衍生物。最后，将合成的吡唑衍生物2a-2m化合物再次重氮化。通过使这些重氮化的化合物与3-氨基-5-羟基-1-苯基吡唑反应，得到了新的13种杂环二偶氮染料（3a-3m）加入了染料文献和染料行业。这些新合成的化合物的结构通过元素分析和光谱方法进行表征，例如傅立叶变换红外光谱-原子吸收全反射率（FT-IR-ATR），1 H-核磁共振（1 H NMR）光谱和质谱。然后研究了在二甲基亚砜，二甲基甲酰胺，乙腈，乙酸，甲醇和氯仿中的溶剂变色性质和溶剂作用。此外，研究了有机和无机酸和碱对化合物吸收光谱的影响以及苯环键合基团的取代作用。
• Synthesis, molecular docking and antimicrobial activity of new fused pyrimidine and pyridine derivatives
  作者：Mohamed A.A. Radwan、Maha A. Alshubramy、Marwa Abdel-Motaal、Bahaa A. Hemdan、Dina S. El-Kady

  DOI：10.1016/j.bioorg.2019.103516

  日期：2020.3

  Synthesis of some new heterocyclic ring systems incorporated pyrimidine and pyridine moieties starting from 1-(furan-2-yl)-3-(thiophen-2-yl) chalcone was achieved. The structure of the new compounds was interpreted by spectral studies and ESI-MS analysis. Antimicrobial investigations of the designated compounds were performed towards some harmful pathogenic microbes. Antimicrobial tests proved that

  合成了一些新的掺入嘧啶和吡啶部分的杂环系统，所述吡啶基和吡啶部分从1-（呋喃-2-基）-3-（噻吩-2-基）查尔酮开始。通过光谱研究和ESI-MS分析解释了新化合物的结构。对某些有害病原微生物进行了指定化合物的抗菌研究。抗菌测试证明，化合物11具有比其他设计的化合物更高的抗菌活性。将化合物11对接到DNA促旋酶B链的活性位点中显示出结合能为-13.05kJ mol-1，距离为3.18Ao。此外，针对目标化合物进入DNA促旋酶B链的对接研究已获批准，其结合能从-13.05扩展至-20.48 kJ mol-1。
• Acidity constant and solvatochromic behavior of some pyrazolo[1,5-a]pyrimidin-2-amine derivatives
  作者：Mohamed A. El-Gahami、Ahmed E.M. Mekky、Tamer S. Saleh、Abdullah S. Al-Bogami

  DOI：10.1016/j.saa.2014.03.029

  日期：2014.8

  medium changing from cyclohexane → carbon tetrachloride → chloroform → ethanol → DMF. The acid dissociation constants of these compounds were determined in aqueous–organic solvent mixtures such as acetone, methanol, ethanol and DMF. The ionization constants of the dyes in question depend largely on both the proportion and the nature of the organic solvent basicity contribute the major effects on the

  研究了吡唑并[1,5-a]嘧啶-2-胺的一些偶氮化合物的紫外可见电子光谱。通过研究它们在不同极性的纯有机溶剂（例如环己烷四氯化碳，氯仿，乙醇和DMF）中的光谱，研究了这些化合物的溶剂变色行为。这些表现出其红移λ最大随着介质相对介电常数的增加，从环己烷→四氯化碳→氯仿→乙醇→DMF改变。这些化合物的酸解离常数是在水性有机溶剂混合物（如丙酮，甲醇，乙醇和DMF）中测定的。所讨论的染料的电离常数在很大程度上取决于比例和有机溶剂碱性的性质，这对电离过程起主要作用。通常，所有化合物的p K a值均随介质相对介电常数的增加而降低。研究的偶氮化合物的酸度按以下顺序增加： 对-NO 2  ＜m-CF 3  ＜pF ＜p-Cl ＜pH ＜p-CH 3。
• REACTIONS OF CHLOROCARBONYL ISOCYANATE WITH 5-AMINOPYRAZOLES AND ACTIVE METHYLENE NITRILES: A NOVEL SYNTHESIS OF PYRAZOLO[1,5-a]-1,3,5-TRIAZINES AND BARBITURATES
  作者：Galal H. Elgemeie、Samia R. El-Ezbawy、Hany A. Ali

  DOI：10.1081/scc-100106205

  日期：2001.1

  Reactions of chlorocarbonyl isocyanate and chlorosulfonyl isocyanate with aminopyrazoles and active methylene nitriles are reported. They lead to novel pyrazolo[1,5-a]-1,3,5-triazines and barbituric acid derivatives. The structures of the products and the mechanisms of their formation are reported.

  氯羰基异氰酸酯和氯磺酰基异氰酸酯与氨基吡唑和活性亚甲基腈的反应已有报道。它们导致新的吡唑并[1,5-a]-1,3,5-三嗪和巴比妥酸衍生物。报道了产物的结构及其形成机制。