N,N'-bis(3,4-dichlorophenyl)hydrazine | 71753-42-9

• 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: N,N'-bis(3,4-dichlorophenyl)hydrazine
• 英文别名: 1,2-bis(3,4-dichlorophenyl)hydrazine；hydrazo(3,4-dichlorobenzene)；3,3',4,4'-Tetrachlorohydrazobenzol；N,N'-Bis-(3,4-dichlor-phenyl)-hydrazin；3.4.3'.4'-Tetrachlor-hydrazobenzol
• CAS: 71753-42-9
• 化学式: C₁₂H₈Cl₄N₂
• 分子量: 322.021
• InChiKey: IPEACQYLDNVWOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3,4-dichlorophenyl)hydrazine 在 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 16.5h， 生成 N,1,2-tris(3,4-dichlorophenyl)-3-hydroxy-5-oxo-pyrazole-4-carboxamide
  参考文献：
  名称：

  Pyrazolidine-3,5-diones and 5-Hydroxy-1H-pyrazol-3(2H)-ones, Inhibitors of UDP-N-acetylenolpyruvyl Glucosamine Reductase

  摘要：

  A series of pyrazolidine-3,5-dione and 5-hydroxy-1H-pyrazol-3(2H)-one inhibitors of Escherichia coli UDP-N-acetylenolpyruvyl glucosamine reductase (MurB) has been prepared. The 5-hydroxy-1H-pyrazol-3(2H)ones show low micromolar IC50 values versus E. coli MurB and submicromolar minimal inhibitory concentrations ( MIC) against Staphylococcus aureus GC 1131, Enterococcus faecalis GC 2242, Streptococcus pneumoniae GC 1894, and E. coli GC 4560 imp, a strain with increased outer membrane permeability. None of these compounds show antimicrobial activity against Candida albicans, a marker of eukaryotic toxicity. Moreover, these compounds inhibit peptidoglycan biosynthesis, as assessed by measuring the amount of soluble peptidoglycan produced by Streptococcus epidermidis upon incubation with compounds. A partial least squares projection to latent structures analysis shows that improving MurB potency and MIC values correlate with increasing lipophilicity of the C-4 substituent of the 5-hydroxy-1H-pyrazol-3(2H)-one core. Docking studies using FLO and PharmDock produced several binding orientations for these molecules in the MurB active site.

  DOI：

  10.1021/jm060499t
• 作为产物：
  描述：

  3,4-二氯硝基苯 在 氨 、 lithium perchlorate 作用下， 以 乙腈 为溶剂， 以47%的产率得到N,N'-bis(3,4-dichlorophenyl)hydrazine
  参考文献：
  名称：

  气态氨化学选择性电化学还原硝基芳烃

  摘要：

  可以通过还原硝基芳烃来合成有价值的芳族氮化合物。在这里，我们报告了通过使用惰性石墨毡作为电极和氨作为还原剂的协议对硝基芳烃进行电化学还原。根据电池电压和溶剂的不同，该协议可用于获得芳族a氧基，偶氮和化合物以及具有高化学选择性的苯胺衍生物。该方案可以轻松放大至> 10 g，而产量不会降低，证明了其潜在的合成效用。提出了逐步的阴极还原途径以依次解释产物的世代。

  DOI：

  10.1039/d1ob00077b

文献信息

• Gaudry; Keirstead, Canadian Journal of Research, Section B: Chemical Sciences, 1949, vol. 27, p. 897,899, 900
  作者：Gaudry、Keirstead

  DOI：——

  日期：——
• Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia
  作者：Liu Chang、Jin Li、Na Wu、Xu Cheng

  DOI：10.1039/d1ob00077b

  日期：——

  Valuable aromatic nitrogen compounds can be synthesized by reduction of nitroarenes. Herein, we report electrochemical reduction of nitroarenes by a protocol that uses inert graphite felt as electrodes and ammonia as a reductant. Depending on the cell voltage and the solvent, the protocol can be used to obtain aromatic azoxy, azo, and hydrazo compounds, as well as aniline derivatives with high chemoselectivities

  可以通过还原硝基芳烃来合成有价值的芳族氮化合物。在这里，我们报告了通过使用惰性石墨毡作为电极和氨作为还原剂的协议对硝基芳烃进行电化学还原。根据电池电压和溶剂的不同，该协议可用于获得芳族a氧基，偶氮和化合物以及具有高化学选择性的苯胺衍生物。该方案可以轻松放大至> 10 g，而产量不会降低，证明了其潜在的合成效用。提出了逐步的阴极还原途径以依次解释产物的世代。
• Pyrazolidine-3,5-diones and 5-Hydroxy-1<i>H</i>-pyrazol-3(2<i>H</i>)-ones, Inhibitors of UDP-<i>N</i>-acetylenolpyruvyl Glucosamine Reductase
  作者：Adam M. Gilbert、Amedeo Failli、Jay Shumsky、Youjun Yang、Anatoly Severin、Guy Singh、William Hu、David Keeney、Peter J. Petersen、Alan H. Katz

  DOI：10.1021/jm060499t

  日期：2006.10.1

  A series of pyrazolidine-3,5-dione and 5-hydroxy-1H-pyrazol-3(2H)-one inhibitors of Escherichia coli UDP-N-acetylenolpyruvyl glucosamine reductase (MurB) has been prepared. The 5-hydroxy-1H-pyrazol-3(2H)ones show low micromolar IC50 values versus E. coli MurB and submicromolar minimal inhibitory concentrations ( MIC) against Staphylococcus aureus GC 1131, Enterococcus faecalis GC 2242, Streptococcus pneumoniae GC 1894, and E. coli GC 4560 imp, a strain with increased outer membrane permeability. None of these compounds show antimicrobial activity against Candida albicans, a marker of eukaryotic toxicity. Moreover, these compounds inhibit peptidoglycan biosynthesis, as assessed by measuring the amount of soluble peptidoglycan produced by Streptococcus epidermidis upon incubation with compounds. A partial least squares projection to latent structures analysis shows that improving MurB potency and MIC values correlate with increasing lipophilicity of the C-4 substituent of the 5-hydroxy-1H-pyrazol-3(2H)-one core. Docking studies using FLO and PharmDock produced several binding orientations for these molecules in the MurB active site.