5-methyl-4-(2-(4-nitrophenyl)hydrazono)-2-phenyl-2,4-dihydro-3H-pyrazol-3one

• 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: 5-methyl-4-(2-(4-nitrophenyl)hydrazono)-2-phenyl-2,4-dihydro-3H-pyrazol-3one
• 英文别名: 4-(4-nitrophenylhydrazono)-3-methyl-1-phenyl-4,5-dihydropyrazole-5-one；3-methyl-4-(2-(4-nitrophenyl)hydrazono)-1-phenyl-1H-pyrazol-5(4H)-one；5-methyl-4-[(4-nitrophenyl)hydrazinylidene]-2-phenylpyrazol-3-one
• 化学式: C₁₆H₁₃N₅O₃
• 分子量: 323.311
• InChiKey: ZUPWRAGGXBPJEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  100.2
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-nitrobenzenediazonium tetrafluoroborate 、 依达拉奉 在 三甲胺 作用下， 20.0 ℃ 、50.0 kPa 条件下， 反应 12.0h， 以98%的产率得到5-methyl-4-(2-(4-nitrophenyl)hydrazono)-2-phenyl-2,4-dihydro-3H-pyrazol-3one
  参考文献：
  名称：

  重氮盐的无废化学反应和固体盐反应中偶联产物的良性分离。

  摘要：

  气固和固固技术可在重氮盐化学过程中实现无浪费的定量合成。研究了用反应性气体NO（2），NO和NOCl重氮化的五种技术。两种类型通过原子力显微镜（AFM）进行了机械研究，并根据已知的晶体堆积进行了解释。相同的原理适用于由一步反应衍生的级联反应。固体重氮盐与固体二苯胺和苯胺定量偶合，得到三氮烯。偶氮偶联通过定量重磨固体重氮盐与β-萘酚和CH酸性杂环（如巴比妥酸或吡唑啉酮）而定量获得。固体重氮盐可以化学计量比更容易地用于溶液中的偶联。固体重氮盐与KI共同研磨可定量获得各种固体芳基碘化物。盐反应中不可避免的偶合产物以高度良性的方式从不溶性产物中完全分离出来。固态反应优于产生大量废料的类似溶液反应。用IR和NMR光谱及质谱法阐明了产物的结构，同时用B3LYP / 6-31G *和BLYP / 6-31G **水平的密度泛函计算研究了化合物的互变异构性质。固态反应优于产生大量废料的类似溶液反应。用IR

  DOI：

  10.1002/1521-3765(20020315)8:6<1395::aid-chem1395>3.0.co;2-l

文献信息

• Room temperature diazotization and coupling reaction using a DES–ethanol system: a green approach towards the synthesis of monoazo pigments
  作者：Sujit Suresh Kamble、Ganapati Subray Shankarling

  DOI：10.1039/c9cc01114e

  日期：——

  An environmentally benign, one-pot diazotization and coupling reaction using ChCl:tartaric acid DES at room temperature is described. The bulky tartrate ion renders stability to the diazonium salt at room temperature, also evidenced by 1H NMR. The isolated diazonium salt is stable and active even after 192 h at room temperature.

  描述了在室温下使用ChCl：酒石酸DES进行的环境友好的一锅重氮化和偶联反应。庞大的酒石酸根离子在室温下对重氮盐也具有稳定性，这也由1 H NMR证实。分离出的重氮盐即使在室温下192小时后仍是稳定且有活性的。
• Tautomerism in azo dyes: Border cases of azo and hydrazo tautomers as possible NMR reference compounds
  作者：V. Deneva、A. Lyčka、S. Hristova、A. Crochet、K.M. Fromm、L. Antonov

  DOI：10.1016/j.dyepig.2019.02.015

  日期：2019.6

  hydrazone tautomers. The tautomeric state is not substantially influenced by nitro group substitution in the phenyl ring. Consequently, the studied compounds can be used as model tautomers in the NMR evaluation of the tautomeric state in various azo dyes in solution. According to the crystallographic data (obtained by us or available in the literature) the conclusions about the tautomerism of the studied

  为了满足互变异构偶氮染料研究中对NMR参考化合物的需求，衍生自3-甲基-1-苯基-4-（苯基二氮烯基）-1H-吡唑-5-胺和5-的两个系列偶氮染料甲基-2-苯基-4-（2-苯基肼基）-2,4-二氢-3H-吡唑-3-酮已通过分子光谱法（UV-Vis和NMR）和量子化学计算（M06- 2X / TZVP）。结果清楚地表明3-甲基-1-苯基-4-（苯基二氮烯基）-1H-吡唑-5-胺以纯偶氮互变异构形式存在，而5-甲基-2-苯基-4-（2-苯基肼基） -2，4-二氢-3H-吡唑-3-酮以互变异构体的形式存在。互变异构状态基本上不受苯环中硝基取代的影响。所以，所研究的化合物可在溶液中各种偶氮染料的互变异构状态的NMR NMR评价中用作模型互变异构体。根据晶体学数据（由我们获得或可从文献中获得），关于所研究化合物在溶液中的互变异构的结论在固态下也是有效的。
• Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties
  作者：Udaya Pratap Singh、Hans Raj Bhat、Amita Verma、Mukesh Kumar Kumawat、Rajinder Kaur、S. K. Gupta、Ramendra K. Singh

  DOI：10.1039/c3ra41604f

  日期：——

  A novel series of phenyl hydrazone bearing pyrazole and pyrimidine hybrid compounds has been designed using the molinspiration toolkit based on Lipinski's rule of five and developed via sequential reactions starting from the diazotization of different anilines and further active methylation with acetyl acetone, ethyl acetoacetate and ethyl cyanoacetate to generate hydrazono derivatives. The target hybrid compounds were synthesized on cyclisation of the resulting hydrazono derivatives with hydrazine, phenyl hydrazine and urea. These molecules have been subsequently tested for anti-HIV activity using TZM-bl cell lines. The MTT assay was also carried out for the cytotoxicity determination of the active compounds. Further, to exemplify the key structural features of the molecules, a molecular docking analysis of the most active compounds was performed at the NNIBP of the HIV-RT protein. The antibacterial activity of the target compounds was also determined against a panel of four Gram-positive and four Gram-negative human pathogens. All molecules showed a potent anti-HIV activity along with a prominent inhibition of bacterial organisms.

  一种新的系列含有吡唑和嘧啶杂合化合物的苯肼酮已被设计，这一设计基于Lipinski五条规则，并通过从不同苯胺的重氮化反应开始，随后与乙酰乙酸、乙基乙酰乙酸和乙基氰乙酸的活性甲基化反应生成肼酮衍生物。目标杂合化合物是在生成的肼酮衍生物与肼、苯肼和尿素环化反应后合成的。这些分子随后在TZM-bl细胞系中进行了抗HIV活性测试。此外，还进行了MTT法以确定活性化合物的细胞毒性。为了说明这些分子的关键结构特征，还对最活跃化合物在HIV-RT蛋白的NNIBP进行了分子对接分析。目标化合物的抗菌活性也针对四种革兰氏阳性菌和四种革兰氏阴性人类病原体进行了检测。所有分子均显示出强效的抗HIV活性以及显著的细菌抑制作用。
• Singh, Vipin Kumar, Indian Journal of Heterocyclic Chemistry, 2014, vol. 23, # 4, p. 429 - 432
  作者：Singh, Vipin Kumar

  DOI：——

  日期：——
• Waste-Free Chemistry of Diazonium Salts and Benign Separation of Coupling Products in Solid Salt Reactions
  作者：Gerd Kaupp、Andreas Herrmann、Jens Schmeyers

  DOI：10.1002/1521-3765(20020315)8:6<1395::aid-chem1395>3.0.co;2-l

  日期：2002.3.15

  and anilines to give the triazenes. Azo couplings are achieved with quantitative yields by cautious co-grinding of solid diazonium salts with beta-naphthol and C-H acidic heterocycles, such as barbituric acids or pyrazolinones. Solid diazonium salts may be more easily applied in a stoichiometric ratio for couplings in solution. Co-grinding of solid diazonium salts with KI gives quantitative yields of

  气固和固固技术可在重氮盐化学过程中实现无浪费的定量合成。研究了用反应性气体NO（2），NO和NOCl重氮化的五种技术。两种类型通过原子力显微镜（AFM）进行了机械研究，并根据已知的晶体堆积进行了解释。相同的原理适用于由一步反应衍生的级联反应。固体重氮盐与固体二苯胺和苯胺定量偶合，得到三氮烯。偶氮偶联通过定量重磨固体重氮盐与β-萘酚和CH酸性杂环（如巴比妥酸或吡唑啉酮）而定量获得。固体重氮盐可以化学计量比更容易地用于溶液中的偶联。固体重氮盐与KI共同研磨可定量获得各种固体芳基碘化物。盐反应中不可避免的偶合产物以高度良性的方式从不溶性产物中完全分离出来。固态反应优于产生大量废料的类似溶液反应。用IR和NMR光谱及质谱法阐明了产物的结构，同时用B3LYP / 6-31G *和BLYP / 6-31G **水平的密度泛函计算研究了化合物的互变异构性质。固态反应优于产生大量废料的类似溶液反应。用IR