3-methoxy-4-hydroxybenzaldehyde-2,4-dinitrophenylhydrazone | 1166-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-methoxy-4-hydroxybenzaldehyde-2,4-dinitrophenylhydrazone
• 英文别名: 4-(2-(2,4-dinitrophenyl)hydrazono)methyl-2-methoxyphenol；vanillin (2,4-dinitrophenyl)hydrazone；vanillin-(2,4-dinitro-phenylhydrazone)；Vanillin-(2,4-dinitro-phenylhydrazon)；<3-Methoxy-4-hydroxy-benzaldehyd>-2.4-dinitro-phenylhydrazon；2-Methoxy-4-(2,4-dinitro-phenylhydrazonomethyl)-phenol；Vanillin-2,4-dinitrophenylhydrazon；4-[[(2,4-dinitrophenyl)hydrazinylidene]methyl]-2-methoxyphenol
• CAS: 1166-13-8
• 化学式: C₁₄H₁₂N₄O₆
• 分子量: 332.272
• InChiKey: UPCLQWFMKFHQAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  香草醛 、 2,4-二硝基苯肼 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以70%的产率得到3-methoxy-4-hydroxybenzaldehyde-2,4-dinitrophenylhydrazone
  参考文献：
  名称：

  Synthesis and Antimicrobial Resistant Modulatory Activity of 2,4-Dinitrophenylhydrazone Derivatives as Agents against Some ESKAPE Human Pathogens

  摘要：

  合成了一个包含六种新型苯基肼酮化合物的图书馆，并针对一系列革兰氏阳性、革兰氏阴性和真菌物种评估了它们的体外抗菌和耐药调节活性。这些化合物的产率高，达到60-92%（重量/重量），并使用熔点、紫外-可见光谱、红外和核磁共振（1H、13C和DEPT-Q）技术进行了表征。质谱技术用于确认其中一种最活性化合物5 [SA5] 的身份。苯基肼酮对所有六种选定的微生物表现出活性，其中最活性化合物1 [BP1] 和5 [SA5] 的最小抑制浓度（MIC）值分别为138 µM（肺炎克雷伯菌）和165 µM（肺炎链球菌）。化合物1 [BP1] 进一步表现出对肺炎链球菌和肺炎克雷伯菌的高耐药调节活性，MIC值为1.078 µM。

  DOI：

  10.1155/2020/2720697

文献信息

• 一种香草醛缩2,4-二硝基苯腙的绿色合成法
  申请人：广东海洋大学

  公开号：CN115160180A

  公开（公告）日：2022-10-11

  本发明公开了一种香草醛缩2,4‑二硝基苯腙的绿色合成法，属于化学合成技术领域，其技术方案要点是：合成步骤如下，S1、称取原料2,4‑二硝基苯肼和香草醛，并将原料放入研磨皿中充分混合，加入氯化铵进行研磨，获得橙红色沉淀；S2、用无水乙醇洗涤橙红色沉淀水浴加热：水浴加热过程中使用玻璃棒搅拌溶解无水乙醇和橙红色沉淀，然后冷却后进行抽滤，获得固体；S3、用蒸馏水洗涤固体，再经过抽滤和无水乙醇重结晶，获得香草醛缩2,4‑二硝基苯腙晶体。本发明主要用于香草醛缩2,4‑二硝基苯腙的绿色合成，避免了有机溶剂的使用及强酸、强腐蚀性试剂作催化剂所造成的对环境的污染；并且本方法具有催化剂便宜易得、后处理简单、粗产品易纯化等优点。
• Acid-Base Indicator Properties of Synthesized Phenylhydrazones: 4-(2-(2,4-Dinitrophenyl) Hydrazono) Methyl)-2 Methoxy Phenol and 4-(2-(2,4-Dinitrophenylhydrazono) Methyl) Benzene-1,3-diol
  作者：Cedric D. K. Amengor、Abena Brobbey、Isaac Ayensu、Emmanuel Orman、Paul Peprah、Billy Mawunyo Abudey、Seth Junior Ayihi、Claudia Naa Dedei Attoh、Alberta Ade、Paul Kwesi Sodzi、James Sarpong Aboagye

  DOI：10.1155/2022/3667814

  日期：2022.9.20

  4-(2-(2,4-Dinitrophenyl) hydrazone) methyl)-2 methoxy phenol (IND-X) and 4-(2-(2, 4-dinitrophenylhydrazono) methyl) benzene-1,3-diol (IND-Y) were synthesised by condensation reactions with 2,4-dinitrinophenylhydrazine and were observed to possess acid-base indicator properties. The study was conducted to explore and verify their use in different analytical situations and, consequently, validate them. Analysis of their use in acid-base titrations between strong acids/strong bases and weak acids/strong bases as well as pharmaceutical applications in the assay of ibuprofen pure powder and batch of ibuprofen tablets (400 mg) using standard methods in the British Pharmacopoeia (2020) was all considered. The validations were performed by the International Conference on Harmonisation of Technical Requirements for the registration of Pharmaceuticals for Humans Q2 (R1) guidelines. The outcomes were statistically compared with existing conventional analytical approaches. Titrimetric data obtained were analyzed statistically by Student’s t-test and one-way ANOVA at a 95% confidence level. IND-X and IND-Y were shown to be similar in behaviour to phenolphthalein, methyl orange, and methyl red as visual indicators after preliminary evidence of sharp colour changes in acid, alkaline, and neutral pH solutions. The use of the two indicators in the assay of ibuprofen powder and tablets has also been established. The validation parameters considered were found to be consistent with respective acceptance criteria for analytical purposes. IND-X and IND-Y are therefore proposed as alternative acid-base indicators to methyl red, methyl orange, and phenolphthalein for routine volumetric analysis in students’ laboratory experiments. They also serve as alternative indicators to phenolphthalein for the titrimetric analysis of ibuprofen-based samples and products.