1-(3-formyl-4-hydroxyphenylazo)-2-chloro-4-nitrobenzene | 84790-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 1-(3-formyl-4-hydroxyphenylazo)-2-chloro-4-nitrobenzene
• 英文别名: Benzaldehyde, 5-[2-(2-chloro-4-nitrophenyl)diazenyl]-2-hydroxy-；5-[(2-chloro-4-nitrophenyl)diazenyl]-2-hydroxybenzaldehyde
• CAS: 84790-28-3
• 化学式: C₁₃H₈ClN₃O₄
• 分子量: 305.677
• InChiKey: QXGWAYYPKLZHPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-formyl-4-hydroxyphenylazo)-2-chloro-4-nitrobenzene 、 二甘醇胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以46%的产率得到1-{3-[(2-hydroxyethoxyethylimino)methyl]-4-hydroxyphenylazo}-2-chloro-4-nitrobenzene
  参考文献：
  名称：

  Synthesis and studies of selective chemosensors for anions and cations by azo-containing salicylaldimine-based receptors

  摘要：

  Three new chromogenic receptors containing electron-withdrawing groups appended to the azophenol moiety were synthesized, characterized, and their chromogenic behavior toward various anions and cations investigated. These chemosensors show visual changes towards biologically relevant anions like F and OH, and also towards various cations such as Cu2+, Co2+, Ni2+, Mn2+, and Zn2+. Yet, other anions such as Cl, Br, and NO3 could not cause any color change. The sensing action was further confirmed by UVVis titration. 1H-NMR experiments were carried out to explore the nature of interaction between receptors with F and OH. The binding constants (K a) of the hostguest complexes formed were determined.

  DOI：

  10.1080/00958972.2012.752818
• 作为产物：
  描述：

  (2-Cl-4-NO2C6H3NH3)Cl 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.75h， 生成 1-(3-formyl-4-hydroxyphenylazo)-2-chloro-4-nitrobenzene
  参考文献：
  名称：

  固定在二氧化硅上的有机硅烷基亚硝酸盐离子液体的纳米颗粒，用于苯胺衍生物的重氮化和随后的偶氮染料的合成

  摘要：

  由N-甲基咪唑与（3-氯丙基）三甲氧基硅烷的反应制备含三甲氧基甲硅烷基的咪唑基亚硝酸盐离子液体。将该离子液体共价固定在二氧化硅上，得到亚硝酸咪唑鎓部分保持完整的纳米颗粒。进行重氮化反应作为模型反应，以检查这些纳米粒子作为硝鎓源的活性。在温和的非均相条件下（室温和较短的反应时间），在HCl存在下，各种苯胺衍生物的重氮化反应均表现出优异的性能。使用标准实验程序，将重氮盐与一系列叔苯胺，苯酚和萘酚进行原位偶联，以高收率提供了必要的偶氮染料。

  DOI：

  10.1016/j.dyepig.2011.09.013

文献信息

• Synthesis and characterization of amino glucose-functionalized silica-coated NiFe2O4 nanoparticles: A heterogeneous, new and magnetically separable catalyst for the solvent-free synthesis of 2,4,5–trisubstituted imidazoles, benzo[d]imidazoles, benzo[d] oxazoles and azo-linked benzo[d]oxazoles
  作者：Leila Zare Fekri、Mohammad Nikpassand、Shahab Shariati、Behnaz Aghazadeh、Reza Zarkeshvari、Nahid Norouz pour

  DOI：10.1016/j.jorganchem.2018.07.008

  日期：2018.9

  NiFe2O4@SiO2@amino glucose supply an environmentally friendly procedure for the synthesis of 2,4,5-trisubstituted imidazoles through one-pot multicomponent condensation of benzil or benzoin, ammonium acetate with aryl aldehydes and for the synthesis of benzoxazoles using condensation reaction of 2-aminophenol with aryl aldehydes under solvent free condition. In the other study, this synthesized magnetically

  化学合成了氨基葡萄糖官能化的二氧化硅包覆的NiFe 2 O 4纳米颗粒（NiFe 2 O 4 @SiO 2 @氨基葡萄糖），并通过透射电子显微镜（TEM），X射线衍射（XRD），热重分析（TGA）进行了表征。 ），能量色散X射线分析（EDX），振动样品磁力计（VSM），Zetasizer和傅里叶变换红外光谱（FT-IR）仪器。NiFe 2 O 4 @SiO 2氨基葡萄糖提供了一种环境友好的方法，该方法可通过联苯或安息香，乙酸铵与芳基醛的一锅多组分缩合来合成2,4,5-三取代的咪唑，以及使用2-氨基苯酚与苯甲酰胺的缩合反应来合成苯并恶唑。无溶剂条件下的芳基醛。在另一项研究中，这种合成的磁性可重复使用的催化剂被引入作为合成苯并[d]的新途径。咪唑利用芳基醛与1,2-二氨基苯之间的反应。这些化合物以高产率和短反应时间获得。该催化剂可以容易地回收并以几乎恒定的活性重复使用五个循环。合成的化合物的特
• A new nitrite ionic liquid (IL-ONO) as a nitrosonium source for the efficient diazotization of aniline derivatives and in-situ synthesis of azo dyes
  作者：Hassan Valizadeh、Ashkan Shomali

  DOI：10.1016/j.dyepig.2010.11.010

  日期：2012.3

  affect the efficient diazotization of arylamines. The diazonium salts thus obtained were coupled, using standard experimental procedures, to a range of tertiary anilines, phenols and naphthols to afford the requisite azo dyes in good yield. The diazotization and subsequent azo-coupling generated the related azo dyes at 0–5 °C in short reaction times with a simple experimental procedure.

  合成了一种新的含特定任务的亚硝酸盐离子液体，该液体由N-甲基-N-羟丁基咪唑啉鎓氯化物的O-亚硝化反应衍生而来，并用作亚硝鎓离子的来源，以影响芳基胺的有效重氮化。使用标准的实验方法，将如此获得的重氮盐与一系列叔苯胺，苯酚和萘酚偶联，以高收率提供所需的偶氮染料。通过简单的实验程序，重氮化和随后的偶氮偶联在较短的反应时间内于0-5°C生成了相关的偶氮染料。
• Ionic liquid 1-(3-Trimethoxysilylpropyl)-3-methylimidazolium nitrite as a new reagent for the efficient diazotization of aniline derivatives and in situ synthesis of azo dyes
  作者：H. Valizadeh、M. Amiri、A. Shomali、F. Hosseinzadeh

  DOI：10.1007/bf03249083

  日期：2011.6

  A new ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite was synthesized. This ionic liquid was used as a convenient nitrosonium source in diazotization of arylamines into their corresponding diazonium salts which were converted into their related azo dyes via the in situ azo-coupling with aniline derivatives or phenolic compounds. The diazotization of anilines in this ionic liquid

  合成了一种新型的离子液体1-（3-三甲氧基甲硅烷基丙基）-3-甲基咪唑鎓亚硝酸盐。这种离子液体被用作芳胺的重氮化了方便亚硝源为它们相应的重氮盐，其被转换成其相关的偶氮染料通过在原位与苯胺衍生物或酚类化合物偶氮耦合。苯胺在该离子液体中的重氮化反应和随后的偶氮偶合反应，可通过简单的实验程序，在较短的反应时间内，在0–5°C的条件下，以优异的产率产生相关的偶氮染料。
• The Coumarin Psoralidin Enhances Anticancer Effect of Tumor Necrosis Factor-Related Apoptosis-Inducing Ligand (TRAIL)
  作者：Joanna Bronikowska、Ewelina Szliszka、Dagmara Jaworska、Zenon P. Czuba、Wojciech Krol

  DOI：10.3390/molecules17066449

  日期：——

  Coumarins are a very common type of secondary plant metabolites with a broad spectrum of biological activities. Psoralidin is a naturally occurring furanocoumarin isolated from Psoralea corylifolia possessing anticancer and chemopreventive properties. Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) triggers apoptosis in cancer cells with no toxicity toward normal tissues. Endogenous TRAIL plays an important role in immune surveillance and defence against cancer cells. Coumarins can modulate TRAIL-mediated apoptosis in cancer cells. We examined the cytotoxic and apoptotic activities of psoralidin in combination with TRAIL on HeLa cancer cells. The cytotoxicity was measured by MTT and LDH assays. The apoptosis was detected using annexin V-FITC staining and mitochondrial membrane potential was evaluated using DePsipher staining by fluorescence microscopy. Death receptor (TRAIL-R1/DR4 and TRAIL-R2/DR5) expression was analyzed using flow cytometry. Psoralidin enhanced TRAIL-induced apoptosis in HeLa cells through increased expression of TRAIL-R2 death receptor and depolarization of mitochondrial membrane potential. Our study indicated that psoralidin augmented the anticancer effects of TRAIL and confirmed a potential use of coumarins in cancer chemoprevention.

  香豆素是一类非常常见的次级植物代谢物，具有广泛的生物活性。普拉利定是一种天然存在的呋喃香豆素，来自小豆蔻（Psoralea corylifolia），具有抗癌和化学预防特性。肿瘤坏死因子相关凋亡诱导配体（TRAIL）能够诱导癌细胞 apoptosis，而对正常组织无毒性。内源性TRAIL在免疫监视和防御癌细胞方面发挥着重要作用。香豆素可以调节癌细胞中TRAIL介导的凋亡。我们研究了普拉利定与TRAIL联合对HeLa癌细胞的细胞毒性和凋亡活性。通过MTT和LDH检测其细胞毒性。采用annexin V-FITC染色法检测凋亡，使用DePsipher染色法通过荧光显微镜评估线粒体膜电位。死受体（TRAIL-R1/DR4和TRAIL-R2/DR5）的表达通过流式细胞术进行分析。普拉利定通过增加TRAIL-R2死受体的表达和线粒体膜电位去极化，增强了HeLa细胞中TRAIL诱导的凋亡。我们的研究表明，普拉利定增强了TRAIL的抗癌效果，确认了香豆素在癌症化学预防中的潜在应用。
• Green synthesis of novel azo-linked 2-phenyl benzimidazoles using ionic liquid [BDBDMIm]Br
  作者：Mohammad Nikpassand、Dornaz Pirdelzendeh

  DOI：10.1016/j.dyepig.2016.03.038

  日期：2016.7

  Benzimidazoles can serve as unique and versatile scaffolds for experimental drug design. Since, a wide range of methods are available for synthesizing benzimidazole nucleus and its derivatives but a real need exists for new procedures that support many kinds of structural diversity and various substitution. In this research, novel series of benzimidazoles were synthesized using the reaction between

  苯并咪唑可以用作实验药物设计的独特且用途广泛的支架。由于有各种各样的方法可用于合成苯并咪唑核及其衍生物，但真正需要支持多种结构多样性和各种取代的新方法。在这项研究中，在催化量为3,3-（丁烷-1,4）的情况下，利用各种合成的水杨醛与萘2,3-二胺或1,2-二氨基苯的反应，合成了一系列新的苯并咪唑系列。一锅法制得-（二基）双（1,2-二甲基-1H-咪唑-3-鎓）Br，而无需其他有机溶剂和氧化剂。IR，1 H NMR和13 C NMR光谱及元素分析用于鉴定这些化合物。