2-cyano-N'-[(1,3-diphenyl-1H-pyrazol-4-yl)methylene]acetohydrazide | 864669-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-cyano-N'-[(1,3-diphenyl-1H-pyrazol-4-yl)methylene]acetohydrazide
• 英文别名: 2-cyano-N'-[(1,3-diphenyl-1h-pyrazol-4-yl)methylidene]acetohydrazide；2-cyano-N-[(1,3-diphenylpyrazol-4-yl)methylideneamino]acetamide
• CAS: 864669-72-7
• 化学式: C₁₉H₁₅N₅O
• 分子量: 329.361
• InChiKey: HIKHKZANOCSLCI-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C(Solv: ethanol (64-17-5); benzene (71-43-2))
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-N'-[(1,3-diphenyl-1H-pyrazol-4-yl)methylene]acetohydrazide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以35%的产率得到1,2-bis((1,3-diphenyl-1H-pyrazol-4-yl)methylene)hydrazine
  参考文献：
  名称：

  一些新型腙、吡唑啉酮、色烯酮、2-吡啶酮和2-吡喃酮衍生物的合成和抗菌活性评价

  摘要：

  氰基乙酰肼衍生物与不同的亲核试剂，如水合肼、对氯苯甲醛和水杨醛进行一系列反应，得到缩合产物。此外，亚芳基丙二腈与不同的含氮亲核试剂，如水合肼、硫代碳酰肼和氰基乙酰肼反应，分别得到肼、腙和吡啶-2-酮衍生物。此外，吡啶-2-one衍生物与不同的碳亲电子试剂反应，如二硫化碳、对氯苯甲醛和乙酸酐。检查了一些化合物的抗微生物活性。

  DOI：

  10.3184/174751917x15065183733150
• 作为产物：
  描述：

  氰乙酰肼 、 1,3-二苯-1H-吡唑-4-甲醛 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到2-cyano-N'-[(1,3-diphenyl-1H-pyrazol-4-yl)methylene]acetohydrazide
  参考文献：
  名称：

  一些新型膦酰基和磷酰基吡唑化合物的合成和光谱表征

  摘要：

  1,3-二苯基-1H-吡唑-4-甲醛 (1) 在亚磷酸二乙酯存在下与苯胺、2-取代苯胺和 P,P-二甲基次膦酰肼反应，得到无环 α-氨基膦酸酯 2、环状 α-氨基膦酸酯分别为 4–6 和 α-肼基膦酸酯 7。此外，用氰基乙酰酰肼、苯乙酮和丙二腈处理醛 1 分别得到缩合产物 8、16 和 21，它们依次与亚磷酸二乙酯和 P,P-二甲基次膦酰肼反应。亚磷酸二乙酯与腙 8 和查耳酮 16 的反应分别产生了新的磷杂环 13 和 18，而它与二氰基亚芳基 21 的反应产生了二氰基吡唑基膦酸酯 22。另一方面，用 P,P 处理腙8 -二甲基次膦酰肼得到意想不到的P，P-二甲基次膦酰腙 15，与亚磷酸二乙酯反应形成 α-肼基膦酸酯 7。此外，通过 P,P-二甲基次膦酰肼与查耳酮 16 和二氰基芳叉 21 的环加成，产生了有趣的 N-磷酰基吡唑 20 和 24分别。通过考虑 IR 光谱、MS、1H-、13C-和

  DOI：

  10.1002/hc.21110

文献信息

• A Facile Synthesis of Some New Thiazolo[3, 2]pyridines Containing Pyrazolyl Moiety and Their Antimicrobial Activity
  作者：T. I. El-Emary、A. Khalil、G. A. M. El-Hag Ali、A. A. A. M. El-Adasy

  DOI：10.1080/10426500490494778

  日期：2005.1.1

  Condensation of 2-cyanomethyl-4-thiazolinone 1 with 1,3-diphenyl-pyrozole-4-carboxaldehyde 2 in ethanol containing a few drops of piperidine yielded the novel methylene derivative 3. Compound 3 was refluxed with malononitrile to give the corresponding thiazolo[3,2-a]pyridine derivative 5. Also, treatment of compound 3 with benzylidenemalononitriles gave the thiazolo[3,2-a]pyridine derivatives 6a-e. Refluxing of compound 6d with triethyl orthoformate furnished the ethoxymethylideneamino derivative 7. Formic acid and malononitrile were reacted with compound 6d to produce thiazolo[3,2-a][1,8]naphthyridine derivative 8 and 11, respectively. Condensation of 2 with cyanoacetohydrazide in ethanol containing piperidine as catalyst gave the hydrazone derivative 12 which, on treatment with salicyaldehyde and 2-cyano-3-(4-fluorophenyl)acrylic acid ethyl ester, yielded the novel chromene 13 and pyridinone 14, respectively Structures of the synthesized compounds have been established by elemental analysis and spectral data. Compounds 3, 5, 6a-d, 8, 11, 13, and 14 have been screened for antimicrobial activities.
• Synthesis of pyrazole encompassing 2-pyridone derivatives as antibacterial agents
  作者：Nisheeth C. Desai、Kiran M. Rajpara、Vivek V. Joshi

  DOI：10.1016/j.bmcl.2013.02.077

  日期：2013.5

  A series of novel compounds 6-amino-1-((1,3-diphenyl-1H-pyrazole-4-yl) methyleneamino)-4-(aryl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles (4a-t) were synthesized and characterized by IR, H-1 NMR, C-13 NMR and mass spectral data. These compounds were screened for their in vitro antibacterial activity against Staphylococcus aureus, Streptococcus pyogenes (Gram positive), Escherichia coli, Pseudomonas aeruginosa (Gram negative) by serial broth dilution and cytotoxic activity (NIH 3T3 & HeLa) by MTT assay. The results indicated that compounds 4g, 4i, 4m, 4o, 4r and 4t exhibit potent antibacterial activity against bacterial strains at non-cytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.
• 2-Cyano-N′-[(1,3-diphenyl-1H-pyrazol-4-yl)methylidene]acetohydrazide in the Synthesis of Nitrogen Heterocycles
  作者：S. K. Ramadan、E. A. E. El-Helw、M. E. Azab

  DOI：10.1134/s1070428019120224

  日期：2019.12

  Some interesting nitrogen heterocycles, as well as other products, were synthesized by reactions of 2-cyano-N'-[(1,3-diphenyl-1H-pyrazol-4-yl)methylidene]acetohydrazide with phenyl isothiocyanate/elemental sulfur, 3,4,5-trimethoxybenzaldehyde, 4-hydroxy-1,1'-biphenyl-3-carbaldehyde, 2-oxoquinoline-3-caraldehyde, triethyl orthoformate, ethyl cyanoacetate, and thiosemicarbazide. The structures of all isolated compounds were established from their analytical and spectral data.