(E)-5-(2-(4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde | 884195-36-2

• 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: (E)-5-(2-(4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde
• 英文别名: (E)-2-hydroxy-5-((4-chlorophenyl)diazenyl)benzaldehyde；(E)-5-((4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde；(E)-5-([4-chlorophenyl]diazenyl)-2-hydroxybenzaldehyde；5-[(E)-(4-chlorophenyl)diazenyl]-2-hydroxybenzaldehyde；5-((4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde；5-(4-chlorophenylazo)salicylaldehyde
• CAS: 884195-36-2
• 化学式: C₁₃H₉ClN₂O₂
• mdl: MFCD00815999
• 分子量: 260.68
• InChiKey: XRNLZEQGHIINEL-FOCLMDBBSA-N

物化性质

• 熔点：
  211-212 °C(Solv: toluene (108-88-3))
• 沸点：
  436.6±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.02
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-5-(2-(4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 C₂₄H₂₃Cl₂N₅NiO₄
  参考文献：
  名称：

  Spectroscopic studies and biological evaluation of some transition metal complexes of azo Schiff-base ligand derived from (1-phenyl-2,3-dimethyl-4-aminopyrazol-5-one) and 5-((4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde

  摘要：

  A series of metal(II) complexes of VO(II), Co(II), Ni(II), Cu(II) and Zn(II) have been synthesized from the azo Schiff base ligand 4-((E)-4-((E)-(4-chlorophenyl)diazenyl)-2-hydroxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (CDHBAP) and characterized by elemental analysis, spectral (IR, UV-Vis, H-1 NMR, ESR and EI-mass), magnetic moment measurements, molar conductance, DNA, SEM, X-ray crystallography and fluorescence studies. The electronic absorption spectra and magnetic susceptibility measurements of the complexes indicate square pyramidal geometry for VO(II) and octahedral geometry for all the other complexes. The important infrared (IR) spectral bands corresponding to the active groups in the ligand and the solid complexes under investigation were studied and implies that CDHBAP is coordinated to the metal ions in a neutral tridentate manner. The redox behavior of copper(II) and vanadyl(II) complexes have been studied by cyclic voltammetry. The nuclease activity of the above metal(II) complexes shows that the complexes cleave DNA. All the synthesized complexes can serve as potential photoactive materials as indicated from their characteristic fluorescence properties. The antibacterial and antifungal activities of the synthesized ligand and its metal complexes were screened against bacterial species (Staphylococcus aureus, Salmonella typhi, Escherichia coli, Bacillus subtilis, Shigella sonnie) and fungi (Candida albicans, Aspergillus niger. Rhizoctonia bataicola). Amikacin and Ketoconozole were used as references for antibacterial and antifungal studies. The activity data show that the metal complexes have a promising biological activity comparable with the parent Schiff base ligand against bacterial and fungal species. The second harmonic generation (SHG) efficiency of the ligand was measured and the NLO (non-linear optical) properties of the ligand are expected to result in the realization of advanced optical devices in optical fiber communication (OFC) and optical computing. The SEM image of the copper(II) complex implies that the size of the particles is 1 mu m. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.05.053
• 作为产物：
  描述：

  对氯苯胺 在 盐酸 、 sodium carbonate 、 sodium hydroxide 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 生成 (E)-5-(2-(4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde
  参考文献：
  名称：

  某些新型含偶氮席夫碱及其Ni（II）配合物的合成，表征和电化学研究

  摘要：

  通过使甲基-2- { N-（2'-氨基乙烷）}-氨基-1-环戊二硫代羧酸甲酯（Hcden）与（E）-2-羟基-5反应制得五个具有NN'OS配位球的新型偶氮-偶氮甲碱配体-（苯基二氮烯基）苯甲醛及其取代的衍生物，然后合成相应的镍（II）配合物。配体和配合物的结构通过元素分析，IR，UV-Vis，1 H NMR光谱和循环伏安法进行表征。（甲基2-（2-（（E）-2-羟基-5-（（E）-对甲苯基二氮烯基）苄基脱甲基氨基）乙基氨基）环戊-1-烯碳二硫基）镍（II）和（甲基2- （2-（（E）-5-（（E）-（4-氯苯基）二氮烯基）-2-羟基亚苄基氨基）乙氨基）环戊-1-烯基碳二硫基）-镍（II）已通过X射线晶体学测定。X射线结果证实了配合物的几何形状是略微扭曲的方平面结构。镍离子与配体的亚胺部分的两个氮原子，二硫代羧酸甲酯的部分的硫原子和酚氧原子配位。

  DOI：

  10.1016/j.dyepig.2013.04.009

文献信息

• One-pot synthesis of novel pyrido[2,3-d]pyrimidines using HAp-encapsulated-γ-Fe2O3 supported sulfonic acid nanocatalyst under solvent-free conditions
  作者：Moona Mohsenimehr、Manouchehr Mamaghani、Farhad Shirini、Mehdi Sheykhan、Fatemeh Azimian Moghaddam

  DOI：10.1016/j.cclet.2014.04.025

  日期：2014.10

  Novel pyrido[2,3-d]pyrimidine derivatives were synthesized through a one-pot three-component approach using HAp-encapsulated-γ-Fe2O3 [γ-Fe2O3@HAp-SO3H] catalyzed condensation of 6-amino-2-(methylthio or ethylthio)pyrimidin-4(3H)-one, Meldrum's acid and aryl aldehydes at 60 °C and under solvent-free conditions. In this protocol the use of nanocatalyst provided a green, useful and rapid method to generate

  通过HAp包封的γ -Fe 2 O 3 [ γ -Fe 2 O 3 @ HAp-SO 3 H]催化缩合反应，通过一锅三组分法合成了新型吡啶并[2,3-d]嘧啶衍生物。 6-氨基-2-（甲硫基或乙硫基）嘧啶-4（3 H）-一，Meldrum的酸和芳基醛，在60°C且无溶剂的条件下。在该协议中，纳米催化剂的使用提供了一种绿色，有用且快速的方法，可在较短的反应时间和优异的产率（88％–94％）下生成产物。
• Regioselective synthesis of 5-aryl azo salicylaldehydes catalyzed by Zn/SBA-15
  作者：Forouzan Zonouzi、Alireza Rahmani、Hamid Dezhampanah、Bahram Ghalami-Choobar、Afsaneh Zonouzi

  DOI：10.1007/s11696-019-00790-1

  日期：2019.10

  Synthesis of (E)-2-hydroxy-5-(aryldiazenyl)benzaldehydes was investigated. Various Lewis acids were tested as catalyst to achieve regioselectivity. In addition to various commercial catalysts, mesoporous Zn/SBA-15 was synthesized through a modified direct method with chloride salt as zinc precursor and characterized using N2-physisorption, low-angle XRD, FESEM and EDX methods; specific surface area of 832 m2 g−1 is a noteworthy result compared to the literature. The synthesized catalyst showed the best results in terms of both total yield and regioselectivity. A scalable two-phase reaction media was used to facilitate both reaction progress monitoring and final product separation. Minimizing solvent consumption, this method can be considered for larger scale production of aryl azo dyes and related compounds.

  研究了(E)-2-羟基-5-(芳基偶氮)苯甲醛的合成，测试了各种路易斯酸作为催化剂以实现区域选择性。除了各种商业催化剂外，还通过改进的直接法合成了介孔Zn/SBA-15，以氯化物盐作为锌前驱体，并通过N₂物理吸附、小角XRD、FESEM和EDX方法进行了表征；与文献相比，比表面积达到832 m² g⁻¹是一个值得注意的结果。合成的催化剂在总收率和区域选择性方面均表现出最佳结果。采用可扩展的两相反应介质，便于反应进程监测和最终产品分离。最小化溶剂消耗，此方法可考虑用于大规模生产芳基偶氮染料及相关化合物。
• Sensitivity and Resolution Development of Spiropyran-based Molecular Photoswitches
  作者：Maryam Heydaripour、Farahnaz Nourmohammadian、Naghi Saadatjoo

  DOI：10.1002/jccs.201600159

  日期：2016.10

  studied. The quality of photochromic reactions of the synthesized photochromic compounds were compared using a dose–response model. Interestingly, by replacing the nitro group in 6‐nitrospiropyran (ε = 0.42 × 104 M−1 cm−1) with a simple phenylazo moiety, the SP form is still colorless and the color intensity of the merocyanine (MC) form is improved desirably by extending the conjugation length (1a, ε = 1

  研究了苯基偶氮部分及其供体和受体取代的衍生物，作为有效的辅助色素，可提高它们的灵敏度和分辨率，以区分分子光开关应用中的螺旋（SP; OFF）和铁（ON）形式。因此，合成了13种偶氮螺并吡喃衍生物，并研究了它们的光谱和光动力学行为。使用剂量反应模型比较了合成光致变色化合物的光致变色反应的质量。有趣的是，通过取代6-硝基螺吡喃中的硝基（ε  = 0.42×10 4  M -1  cm -1）具有简单的苯基偶氮部分，SP形式仍然是无色的，并且通过延长共轭长度（1a，ε  = 1.35×10 4  M -1 cm -1）理想地改善了花青（MC）形式的色强度。在苯偶氮部分对位的亲水性OH基或CH 3基的存在显示出与1a大致相同的光致变色特性。在偶氮苯部分对位的苯偶氮部分的6位上取代的OCH 3基团有效地提高了光致变色特性，SP到MC切换的最大k值。同时，Cl，Br，COOH和NO与1a相比，偶氮苯部
• Some polyhydroxy azo–azomethine derivatives of salicylaldehyde: Synthesis, characterization, spectroscopic, molecular structure and antimicrobial activity studies
  作者：Mustafa Odabaşoğlu、Çiğdem Albayrak、Reşit Özkanca、Fatma Zehra Aykan、Peter Lonecke

  DOI：10.1016/j.molstruc.2006.11.025

  日期：2007.9

  Abstract Some new substituted polyhydroxy azo–azomethine compounds were prepared by reaction of tris(hydroxymethyl)aminomethane with (E)-2-hydroxy-5-(phenyldiazenyl) benzaldehyde and its substituted derivatives. The structures of azo and azo–azomethine compounds were determined by IR, UV–vis, 1H NMR and 13C NMR spectroscopic techniques, and/or X-ray diffraction studies. According to IR spectra, all

  摘要 通过三(羟甲基)氨基甲烷与(E)-2-羟基-5-(苯基二氮烯基)苯甲醛及其取代衍生物反应制备了一些新型取代的多羟基偶氮-偶氮甲碱化合物。偶氮和偶氮甲碱化合物的结构通过 IR、UV-vis、1H NMR 和 13C NMR 光谱技术和/或 X 射线衍射研究确定。根据红外光谱，所有的偶氮甲碱化合物在固态下均采用酮形式。UV-vis 分析表明，所有偶氮-偶氮甲碱化合物在溶液中都存在酮-烯醇互变异构现象，除了硝基取代的衍生物，烯醇形式在溶液中占主导地位。同时，对上述衍生化合物的抗菌性能进行了体外研究。在测试的苯基偶氮水杨醛系列化合物中，4-苯基偶氮水杨醛、4-(3-氯苯基偶氮)水杨醛、4-(2-氯苯基偶氮)水杨醛、4-(4-氟苯基偶氮)水杨醛、4-(3-氯苯基偶氮)水杨醛和4-(4-乙基苯基偶氮)水杨醛仅表现出微弱的抗菌活性对抗革兰氏阳性菌。相反，苯偶氮水杨醛系列化合物与三（羟甲基）氨基甲烷
• Novel C-2 Symmetric Molecules as α-Glucosidase and α-Amylase Inhibitors: Design, Synthesis, Kinetic Evaluation, Molecular Docking and Pharmacokinetics
  作者：Danish Shahzad、Aamer Saeed、Fayaz Ali Larik、Pervaiz Ali Channar、Qamar Abbas、Mohamed F. Alajmi、M. Ifzan Arshad、Mauricio F. Erben、Mubashir Hassan、Hussain Raza、Sung-Yum Seo、Hesham R. El-Seedi

  DOI：10.3390/molecules24081511

  日期：——

  A series of symmetrical salicylaldehyde-bishydrazine azo molecules, 5a–5h, have been synthesized, characterized by 1H-NMR and 13C-NMR, and evaluated for their in vitro α-glucosidase and α-amylase inhibitory activities. All the synthesized compounds efficiently inhibited both enzymes. Compound 5g was the most potent derivative in the series, and powerfully inhibited both α-glucosidase and α-amylase.

  已经合成了一系列对称的水杨醛-双肼偶氮分子，5a-5h，用 1H-NMR 和 13C-NMR 表征，并评估了它们的体外 α-葡萄糖苷酶和 α-淀粉酶抑制活性。所有合成的化合物都有效地抑制了这两种酶。化合物5g是该系列中最有效的衍生物，对α-葡萄糖苷酶和α-淀粉酶都有很强的抑制作用。5g 对 α-葡萄糖苷酶的 IC50 值为 0.35917 ± 0.0189 µM（标准阿卡波糖 IC50 = 6.109 ± 0.329 µM），5g 对 α-淀粉酶的 IC50 值为 0.4379 ± 0.0423 µM，标准卡波糖 IC50 = 6.0423 µM。3.0423 µM。19 Lineweaver-Burk 图表明化合物 5g 是 α-葡萄糖苷酶的竞争性抑制剂。通过分子对接研究证实了最活跃的类似物的结合相互作用。对接研究表明，5g 与残基 Trp690、Asp548、Arg425 和 Glu426