3-氨基-5-羟基-4-苯基氮杂吡唑 | 6627-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氨基-5-羟基-4-苯基氮杂吡唑
• 英文名称: 5-Amino-3-hydroxy-4-phenylazopyrazol
• 英文别名: 5-amino-2H-pyrazole-3,4-dione 4-phenylhydrazone；5-amino-4-phenyldiazenyl-1,2-dihydropyrazol-3-one
• CAS: 6627-93-6
• 化学式: C₉H₉N₅O
• 分子量: 203.203
• InChiKey: ORRWSNWFDNFTLA-UHFFFAOYSA-N

物化性质

• 熔点：
  256 °C (decomp)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.9
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933199090

SDS

3-氨基-5-羟基-4-苯基氮杂吡唑MSDS英文版

反应信息

• 作为反应物：
  描述：

  苄烯丙二腈 、 3-氨基-5-羟基-4-苯基氮杂吡唑 以 吡啶 为溶剂， 反应 3.0h， 以55%的产率得到7-amino-2-hydroxy-5-phenyl-3-phenylazopyrazolo<1,5-a>pyrimidine-6-carbonitrile
  参考文献：
  名称：

  Hilmy Elnagdi, Mohamed; Hassen Taha, Nadia; Abdel Maksoud Abd El All, Fatma, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 4, p. 1082 - 1091

  摘要：

  DOI：
• 作为产物：
  描述：

  α-carboxamido-α-phenylhydrazonoacetonitrile 在 一水合肼 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 以96%的产率得到3-氨基-5-羟基-4-苯基氮杂吡唑
  参考文献：
  名称：

  Ibrahim, Mohamed Kamal Ahmed; El-Moghayar, Mohamed Riffat Hamza, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 832 - 835

  摘要：

  DOI：

文献信息

• Synthesis of Pyrazolo[5,1–c][1,2,4]triazines, Isoxazolo[3,4-e]pyrazolo-[5,1–c][1,2,4]triazines and Aminopyridones
  作者：Kamal U. Sadek、Nadia S. Ibrahim、Mohamed H. Elnagdi

  DOI：10.1002/ardp.19883210306

  日期：——

  Novel pyrazolo[5,1‐c][1,2,4]triazines, isoxazolo[3,4‐e]pyrazolo[5,1‐c]‐[1,2,4]triazines and aminopyridones were synthesised using potassium cyanoacetohydroxamate (1) as starting component.

  使用氰基乙酰异羟肟酸钾合成新型吡唑并 [5,1-c] [1,2,4] 三嗪、异恶唑并 [3,4-e] 吡唑并 [5,1-c] - [1,2,4] 三嗪和氨基吡啶酮(1) 作为起始组件。
• Regioselectivity in the multicomponent reaction of 5-aminopyrazoles, cyclic 1,3-diketones and dimethylformamide dimethylacetal under controlled microwave heating
  作者：Kamal Usef Sadek、Ramadan Ahmed Mekheimer、Tahany Mahmoud Mohamed、Moustafa Sherief Moustafa、Mohamed Hilmy Elnagdi

  DOI：10.3762/bjoc.8.3

  日期：——

  The multicomponent reaction of 5-aminopyrazole derivatives with cyclic 1,3-dicarbonyl compounds and dimethylformamide dimethylacetal (DMFDMA) in DMF at 150 °C under controlled microwave heating afforded regioselectively 8,9-dihydropyrazolo[1,5-a]quinazolin-6(7H)-ones 6 rather than the corresponding dihydropyrazolo[5,1-b]quinazolin-8(5H)-ones 4.

  5-氨基吡唑衍生物与环状1,3-二羰基化合物和二甲基甲醛二甲基缩醛（DMFDMA）在DMF中以控制的微波加热条件下发生多组分反应，得到了具有区域选择性的8,9-二氢吡唑并[1,5-a]喹唑啉-6(7H)-酮6，而不是相应的二氢吡唑并[5,1-b]喹唑啉-8(5H)-酮4。
• Chemoselective Three Component Reactions of 3-Aminopyrazoles, Aldehydes and Malononitrile: Optimize the Structures and Compute the Energies of Possible Tautomers
  作者：Hassan Sheibani、Vahid Saheb、Marjan Rezaei、Mahboobeh Zahedifar

  DOI：10.2174/15701786113106660066

  日期：2014.1.31

  A chemoselective synthesis of 7-amino-5-aryl-2-hydroxy-3-(aryldiazenylpyrazolo[1,5-a]pyrimidine-6- carbonitriles and 4-((7-amino-6-cyano-2-hydroxy-5-arylpyrazolo[1,5-a]pyrimidine-3-yl)diazenyl)benzenesulfonamides through three-component reaction of 3-aminopyrazoles, aldehydes and malononitrile in the presence of base catalysts such as sodium acetate, pyridine and high surface area MgO is reported. 3-Amino pyrazoles were prepared by refluxing of ethyl(arylazo) cyanoacetates with hydrazine hydrate in ethanol. Structures of the new compounds were established by their spectral data and theoretical results. Density Functional Theory (DFT) calculations have been performed to optimize the structure of products. The theoretical results are in good agreement with experimental findings. The theoretical results are compared with the experimetal data. DFT calculations reveal that the enol form of 6 is the most stable molecule.

  通过 3-氨基吡唑、醛类和丙二腈三组分反应，化学选择性合成 7-氨基-5-芳基-2-羟基-3-(芳基偶氮基吡唑并[1,5-a]嘧啶-6-甲腈)和 4-((7-氨基-6-氰基-2-羟基-5-芳基吡唑并[1.5-a]嘧啶-3-基)偶氮基)苯磺酰胺、3-氨基吡唑、醛类和丙二腈在醋酸钠、吡啶和高比表面积氧化镁等碱催化剂存在下通过三组分反应制备的苯磺酰胺。3-Amino 吡唑是通过乙基（芳基偶氮）氰乙酸酯与水合肼在乙醇中的回流反应制备的。通过光谱数据和理论结果确定了新化合物的结构。为了优化产品的结构，还进行了密度泛函理论（DFT）计算。理论结果与实验结果十分吻合。理论结果与实验数据进行了比较。DFT 计算显示，6 的烯醇形式是最稳定的分子。
• Reaction of (chloro carbonyl) phenyl ketene with 5-amino pyrazolones: Synthesis, characterization and theoretical studies of 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives
  作者：Mahboobeh Zahedifar、Razieh Razavi、Hassan Sheibani

  DOI：10.1016/j.molstruc.2016.07.043

  日期：2016.12

  Abstract New 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5- a ]pyrimidine-2,5(1 H ,4 H )-dione derivatives were synthesized from the reaction of (chlorocarbonyl)phenyl ketene and 5-amino pyrazolones in high to excellent yields and short reaction times. Structures of the new compounds were fully characterized by their spectral data IR, 1 H NMR, and 13 C NMR and by the theoretical results. Density

  摘要 由(氯羰基)苯基乙烯酮与(氯羰基)苯基乙烯酮反应合成了新的7-羟基-6-苯基-3-(苯基二氮烯基)吡唑并[1,5-a]嘧啶-2,5(1 H ,4 H)-二酮衍生物。 5-氨基吡唑啉酮以高到极好的收率和较短的反应时间。新化合物的结构通过其光谱数据 IR、 1 H NMR 和 13 C NMR 以及理论结果进行了充分表征。密度泛函理论 (DFT) 用于优化结构，计算所需产品的能量和振动频率 IR 和 1 H NMR 屏蔽张量。将理论结果与实验数据进行了比较。
• Novel Mercaptopurine and Thioguanine Analogues: The Reaction of Dimethyl <i>N</i>‐Cyanodithioiminocarbonate with Oxo‐ and Amino‐diazoles
  作者：Siham Y. Alqaradawi、Galal H. Elgemeie

  DOI：10.1081/scc-120028352

  日期：2004.12.31

  A novel and efficient method for the synthesis of a new variety of methylsulfanyl derivatives of azoloazines and azoloazoles by the reaction of dimethyl N-cyanodithioiminocarbonate with diazoles containing oxo-and amino functions. The synthetic potential of the method is demonstrated.