Benzaldehyd-4-fluorbenzoylhydrazon | 62433-15-2

• 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: Benzaldehyd-4-fluorbenzoylhydrazon
• 英文别名: N-(benzylideneamino)-4-fluorobenzamide
• CAS: 62433-15-2
• 化学式: C₁₄H₁₁FN₂O
• mdl: MFCD00812372
• 分子量: 242.253
• InChiKey: WFTMUPMNCOTYAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 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：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzaldehyd-4-fluorbenzoylhydrazon 在 Co(dmgH)(dmgH₂)Cl₂ 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 乙腈 为溶剂， 以95 %的产率得到2-(4-氟苯基)-5-苯基-1,3,4-恶二唑
  参考文献：
  名称：

  无氧化剂条件下光氧化还原/钴催化级联氧化合成 2,5-二取代 1,3,4-恶二唑

  摘要：

  通过使用有机吖啶光催化剂和钴肟催化剂，开发了一种有效的无氧化剂、光氧化还原介导的级联环化策略，用于合成 1,3,4-恶二唑。各种酰腙已转化为相应的1,3,4-恶二唑产品，收率高达96%，H 2是唯一的副产物。机理实验和密度泛函理论 (DFT) 计算研究表明，光激发 Mes–Acr + *氧化以及去质子化产生的 π 自由基是以碳为中心的自由基，而不是以氧为中心的自由基，这是造成这种转变的原因。该方法的实用性突出是直接从市售醛和酰肼开始的一锅克级合成。

  DOI：

  10.1021/acs.joc.3c01078
• 作为产物：
  描述：

  4-氟苯甲酰肼 、 苯甲醛 以 乙腈 为溶剂， 生成 Benzaldehyd-4-fluorbenzoylhydrazon
  参考文献：
  名称：

  使用 FeBr3 催化剂和过氧化氢，从醛和酰肼衍生物中绿色氧化环化生成 2,5-二取代-1,3,4-恶二唑

  摘要：

  2,5-二取代-1,3,4-恶二唑已开发出在水溶液存在下使用催化量的 FeBr 3将醛和酰肼衍生物氧化环化以获得 2,5-二取代-1,3,4-恶二唑过氧化氢作为氧化剂。通过合成35个2,5-二取代1,3,4-恶二唑实例，证明该方法具有适用范围广、条件温和、耐空气/水、操作简单等优点。更重要的是，它有望在有机合成中得到广泛的应用。

  DOI：

  10.1016/j.tetlet.2023.154783

文献信息

• Photoredox/Cobalt-Catalyzed Cascade Oxidative Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles under Oxidant-Free Conditions
  作者：Jun-Li Li、Hao-Yuan Li、Shan-Shan Zhang、Shigang Shen、Xiu-Long Yang、Xiaoying Niu

  DOI：10.1021/acs.joc.3c01078

  日期：2023.11.3

  An efficient oxidant-free, photoredox-mediated cascade cyclization strategy for the synthesis of 1,3,4-oxadiazoles by using an organo acridinium photocatalyst and a cobaloxime catalyst has been developed. Various acylhydrazones have been transformed into the corresponding 1,3,4-oxadiazole products in up to 96% yield, and H2 is the only byproduct. Mechanistic experiments and density functional theory

  通过使用有机吖啶光催化剂和钴肟催化剂，开发了一种有效的无氧化剂、光氧化还原介导的级联环化策略，用于合成 1,3,4-恶二唑。各种酰腙已转化为相应的1,3,4-恶二唑产品，收率高达96%，H 2是唯一的副产物。机理实验和密度泛函理论 (DFT) 计算研究表明，光激发 Mes–Acr + *氧化以及去质子化产生的 π 自由基是以碳为中心的自由基，而不是以氧为中心的自由基，这是造成这种转变的原因。该方法的实用性突出是直接从市售醛和酰肼开始的一锅克级合成。
• Milcent, Rene; Barbier, Geo, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 77 - 80
  作者：Milcent, Rene、Barbier, Geo

  DOI：——

  日期：——
• Synthesis and biological activity of hydrazide–hydrazones and their corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles
  作者：Bedia Koçyiğit-Kaymakçıoğlu、Emine Elçin Oruç-Emre、Seda Ünsalan、Nurhayat Tabanca、Shabana Iqrar Khan、David Earl Wedge、Gökalp İşcan、Fatih Demirci、Sevim Rollas

  DOI：10.1007/s00044-011-9882-z

  日期：2012.11

  Various 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles (11-20) were prepared by the reaction of aryl substituted hydrazones of 4-fluorobenzoic acid hydrazide (1-10) with acetic anhydride. The structures of the synthesized compounds 11-20, were confirmed by UV, IR, H-1-NMR and mass spectroscopic methods. Antifungal evaluation of the hydrazide-hydrazones 1-10 and corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles 11-20, against clinical and standard Candida pathogens have been performed by using agar diffusion to indentify the active compounds, which were later subjected to a broth microdilution assay to justify the activity level in terms of minimum inhibitory concentrations (MIC). 4-Fluorobenzoic acid [(5-bromothiophen-2-yl)methylene]hydrazide, showed the highest inhibitory activity against Candida albicans (MIC: 125 mu g/ml), and when compared with ketoconazole. In addition, bioauthographic antifungal activity against plant pathogenic fungi such as Colletotrichum, Botrytis, Fusarium, and Phomopsis was conducted. 4-Fluorobenzoic acid [(5-bromothiophen-2-yl)methylene]hydrazide was the most active analog against P. viticola with 91% inhibition at 30 mu M after 144 h. Furthermore, known and the newly synthesized compounds were also screened through a panel of bioassays to determine their anti-inflammatory, cytotoxic, and antioxidant activities in mammalian cells. 3-Acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole, showed a strong inhibition of NF-kappa B-dependent transcription in SW1353 cells with IC50 value of 0.75 mu g/ml. 4-Fluorobenzoic acid [(3-hydroxy-4-methoxyphenyl)methylene]hydrazide, and 3-acetyl-5-(4-fluorophenyl)-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole on intracellular ROS generation in PMA induced HL-60 cells demonstrated potent activity with IC50 values of 0.9 mu g/ml. A strong inhibition of the activity of iNOS activity in LPS induced RAW 264.7 cells was observed for 3-acetyl-5-(4-fluorophenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1,3,4-oxadiazole with IC50 value of 0.3 mu g/ml.