2-hydroxy-3-methoxy-5-((4-methoxyphenyl)diazenyl)benzaldehyde | 341494-76-6

• 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: 2-hydroxy-3-methoxy-5-((4-methoxyphenyl)diazenyl)benzaldehyde
• 英文别名: 2-hydroxy-3-methoxy-5-[(E)-(4-methoxyphenyl)diazenyl]benzaldehyde；2-hydroxy-3-methoxy-5-[(4-methoxyphenyl)diazenyl]benzaldehyde
• CAS: 341494-76-6
• 化学式: C₁₅H₁₄N₂O₄
• mdl: MFCD19288457
• 分子量: 286.287
• InChiKey: RHHOPCROFTVBRD-UHFFFAOYSA-N

物化性质

• 沸点：
  478.3±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-methoxy-5-((4-methoxyphenyl)diazenyl)benzaldehyde 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 bis(2-(hydroxyimino)methyl)-6-methoxy-4-(((4-methoxyphenyl)diazenyl)phenoxy)nickel
  参考文献：
  名称：

  In-vitro antibacterial activity of Ni(II), Cu(II), and Zn(II) complexes incorporating new azo-azomethine ligand possessing excellent antioxidant, anti-inflammatory activity and protective effect of free radicals against plasmid DNA

  摘要：

  Azo Schiff base ligand 2-hydroxy-3-methoxy-5-(tolyldiazenyl)benzaldehyde oxime (HL1) and 2-hydroxy-3-methoxy-5-(methoxyphenyl)benzaldehyde oxime (HL2) were prepared along with their transition metal complexes of Ni(II), Cu(II), and Zn(II). Ligands and their metal complexes were characterized by several analysis techniques. In- vitro antibacterial, antioxidant and anti-inflammatory activities of synthesized ligands and their metal complexes have been studied. Biological study showed that amongst all the synthesized compounds, Cu(II) complexes possessed excellent antibacterial activity than standard antibiotic Chloramphenicol. Ligands (HL1) and (HL2) showed excellent antioxidant as well as anti-inflammatory activity. Both the ligands were tested for their protective effect of free radicals against plasmid DNA and it was found that both the ligands showed good DNA nicking activity.

  DOI：

  10.1080/00397911.2019.1663213
• 作为产物：
  描述：

  甲氧苯胺 、 邻香草醛 在 sodium carbonate 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 2-hydroxy-3-methoxy-5-((4-methoxyphenyl)diazenyl)benzaldehyde
  参考文献：
  名称：

  基于偶氮染料-硫代半氨基偶氮化合物的阴离子简单裸眼比色化学传感器的合成与评价

  摘要：

  一系列新型的，高度选择性的基于偶氮染料的硫代半氨基偶氮阴离子传感器（3e – f）是由硫代氨基脲与六种不同的偶氮水杨醛之间的缩合反应合成的。传感器的结构通过光谱法确认。通过肉眼和紫外可见光谱确定乙酸根阴离子相对于其他阴离子（例如氟离子，氯离子，碘离子和磷酸二氢根阴离子）识别的选择性和敏感性。仅在水溶液中添加乙酸根阴离子（水/二甲亚砜，7：3，v / v）后，含传感器的溶液的颜色才从浅黄色变为橙色，而其他阴离子则不会引起明显的颜色变化。通过紫外可见滴定和1 H NMR光谱监测通过质子转移受体的阴离子识别特性。在传感器水溶液中的条件下3e（水/二甲亚砜，7：3，v / v），乙酸根阴离子定量的线性范围为1–22μM，乙酸根阴离子的检出限（LOD）为0.71μM。

  DOI：

  10.1016/j.saa.2013.10.086

文献信息

• New 1,3-diazabicyclo-[3.1.0]hex-3-ene photochromic azo dyes: Synthesis, characterization and spectroscopic studies
  作者：Nosrat O. Mahmoodi、Meysam Pasandideh Nadamani、Tahereh Behzadi

  DOI：10.1016/j.molliq.2013.05.026

  日期：2013.11

  Ten new 1,3-diazabicyclo-[3.1.0]hex-3-ene-based azo dyes (3a–3k) were synthesized via three-component reaction between [3-(x-phenyl)aziridin-2-yl](phenyl)methanone (x = 4-NO2, 3-NO2), NH4OAc and azo-coupled o-vanillin or salicylaldehyde precursors (1a–1e) and characterized by UV–Vis, IR and 1H NMR spectroscopic techniques. The synthesized azo dyes undergo ring opening in EtOH by irradiation with 254 nm

  通过[3-（x-苯基）叠氮基-2-基]（-）之间的三组分反应，合成了十种新的1,3-二氮杂双环-[3.1.0] hex-3-ene基偶氮染料（3a - 3k）。苯基）甲酮（x = 4-NO 2，3 -NO 2），NH 4 OAc和偶氮偶联的邻香兰素或水杨醛前体（1a - 1e），并通过UV-Vis，IR和1 H NMR光谱技术表征。合成的偶氮染料通过用254 nm紫外线照射在EtOH中开环。分析了这些染料的性质和光致变色结构行为关系（PSBR）。该光谱信息表明，特写Ë普通的室内光中主要使用光敏异构体，但是通过紫外光照射，开放Z型光敏异构体非常突出。
• A triangular dysprosium with asymmetric central caps featuring ferromagnetic coupling and single-molecule magnet behaviour
  作者：Si Shen、Shufang Xue、Shuang-Yan Lin、Lang Zhao、Jinkui Tang

  DOI：10.1039/c3dt51235e

  日期：——

  Dy3 triangle bridged by a deprotonated alkoxyl group of a Schiff-base ligand together with a μ3-OH group has been prepared, in which intramolecular ferromagnetic interactions and single molecule magnet behaviour have been observed.

  一种新的Dy 3三角形桥接由去质子化的烷氧基中的席夫碱配体一起与μ 3 -OH基团已被制备，其中使用分子内相互作用铁磁和单分子磁体行为已经观察到。
• Synthesis, characterization and computational study on potential inhibitory action of novel azo imidazole derivatives against COVID-19 main protease (Mpro: 6LU7)
  作者：Abhijit Chhetri、Sailesh Chettri、Pranesh Rai、Dipu Kumar Mishra、Biswajit Sinha、Dhiraj Brahman

  DOI：10.1016/j.molstruc.2020.129230

  日期：2021.2
• Novel Schiff base scaffolds derived from 4‐aminoantipyrine and 2‐hydroxy‐3‐methoxy‐5‐(phenyldiazenyl)benzaldehyde: Synthesis, antibacterial, antioxidant and anti‐inflammatory
  作者：Mangesh S. Kasare、Pratik P. Dhavan、Aksh Hina I. Shaikh、Bhaskar L. Jadhav、Suresh D. Pawar

  DOI：10.1002/jmr.2976

  日期：2022.9

  AbstractThe synthesis of four new azo‐Schiff base ligands from 2‐hydroxy‐3‐methoxy‐5‐(phenyldiazenyl)benzaldehyde and 4‐aminoantipyrine is described in this study. The molecular structures of all the scaffolds were confirmed using NMR spectroscopies such as 1H and 13C, as well as FT‐IR and Mass spectroscopy. After successful synthesis and characterization of all the ligands, their in vitro antibacterial, antioxidant and anti‐inflammatory activities were carried out by using standard protocols. Results revealed that all the four ligands (L1‐L4) possessed excellent biological potency.
• Synthesis and evaluation of simple naked-eye colorimetric chemosensors for anions based on azo dye-thiosemicarbazones
  作者：Widchaya Radchatawedchakoon、Withsakorn Sangsuwan、Senee Kruanetr、Uthai Sakee

  DOI：10.1016/j.saa.2013.10.086

  日期：2014.3

  selective azo dye-thiosemicarbazones based anion sensors (3e–f) have been synthesized from the condensation reaction between thiosemicarbazide and six different azo salicylaldehydes. The structure of the sensors was confirmed by spectroscopic methods. The selectivity and sensitivity in the recognition for acetate anion over other anions such as fluoride, chloride, iodide and dihydrogenphosphate anions were

  一系列新型的，高度选择性的基于偶氮染料的硫代半氨基偶氮阴离子传感器（3e – f）是由硫代氨基脲与六种不同的偶氮水杨醛之间的缩合反应合成的。传感器的结构通过光谱法确认。通过肉眼和紫外可见光谱确定乙酸根阴离子相对于其他阴离子（例如氟离子，氯离子，碘离子和磷酸二氢根阴离子）识别的选择性和敏感性。仅在水溶液中添加乙酸根阴离子（水/二甲亚砜，7：3，v / v）后，含传感器的溶液的颜色才从浅黄色变为橙色，而其他阴离子则不会引起明显的颜色变化。通过紫外可见滴定和1 H NMR光谱监测通过质子转移受体的阴离子识别特性。在传感器水溶液中的条件下3e（水/二甲亚砜，7：3，v / v），乙酸根阴离子定量的线性范围为1–22μM，乙酸根阴离子的检出限（LOD）为0.71μM。