2-硝基吩嗪 | 3442-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-硝基吩嗪
• 英文名称: 2-nitrophenazine
• 英文别名: 2-nitro-phenazine；2-Nitro-phenazin；2-Nitrophenazin
• CAS: 3442-62-4
• 化学式: C₁₂H₇N₃O₂
• 分子量: 225.206
• InChiKey: XMPQBEJBTADGKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-硝基吩嗪 在 甲醇 、 钯 作用下， 生成 2-氨基吩嗪
  参考文献：
  名称：

  Studies on Phenazines. VII. : Nitration of Phenazine and its Derivatives.

  摘要：

  DOI：

  10.1248/cpb1953.2.283
• 作为产物：
  描述：

  2,4-二硝基二苯胺 生成 2-硝基吩嗪
  参考文献：
  名称：

  Maffei; Aymon, Gazzetta Chimica Italiana, 1954, vol. 84, p. 667,672

  摘要：

  DOI：

文献信息

• Investigation on the photoreactions of nitrate and nitrite ions with selected azaarenes in water
  作者：Toralf Beitz、Wolfgang Bechmann、Rolf Mitzner

  DOI：10.1016/s0045-6535(98)00188-x

  日期：1999.1

  spectrum of oxidized products corresponded to the one got in the photoreactions of azaarenes with hydrogen peroxide. The formation of several oxidation and nitration products of the pyridine ring with its low electron density was explained by the reaction of excited states of azaarenes. The photoreactions with nitrite ions only led to the formation of oxidized and nitrated products. Nitroso products were not

  在λ= 313 nm的辐射下研究了选定的氮杂芳烃与硝酸根和亚硝酸根离子的光反应。两种阴离子的激发导致几种光化学反应，主要形成羟基自由基和氮氧化物。天然水的净化能力，即无机物和有机物的氧化，是由于羟基的形成。在所研究的光反应的主要产物中发现了氮杂氮杂的硝化异构体。氮氧化物负责产生具有高毒性潜力的硝化衍生物。它们的形成可以通过两种机制的平行发生来解释，即分子机制和自由基机制。随着氮杂芳烃电离势的增加，分子机理变得越来越重要。氧化产物的光谱对应于氮杂芳烃与过氧化氢的光反应所得到的光谱。低电子密度的吡啶环的几种氧化和硝化产物的形成可以通过氮杂芳烃的激发态反应来解释。与亚硝酸根离子的光反应仅导致形成氧化和硝化的产物。亚硝基产物未形成。一氧化氮的反应性对于与氮杂芳烃的反应而言太低。与亚硝酸根离子的光反应仅导致形成氧化和硝化的产物。亚硝基产物未形成。一氧化氮的反应性对于与氮杂芳烃的反应而言太低。与亚硝酸
• An umpolung strategy for rapid access to thermally activated delayed fluorescence (TADF) materials based on phenazine
  作者：Huaxing Zhang、Qiang Guo、Hu Cheng、Chunhao Ran、Di Wu、Jingbo Lan

  DOI：10.1039/d1cc06705b

  日期：——

  radical nucleophilic addition/rearrangement of 2-aryl diazaboroles has been accomplished for the first time to construct phenazine structures. This protocol is an umpolung strategy based on the classical electrophilic mechanism, and therefore, a reversed regioselectivity was observed, which provides an opportunity to prepare sterically hindered phenazines. The resulting thermally activated delayed fluorescence

  在此，Ag(I) 促进的 2-芳基二氮杂硼的区域选择性分子内自由基亲核加成/重排首次实现了构建吩嗪结构。该协议是一种基于经典亲电机制的 umpolung 策略，因此观察到了反向的区域选择性，这为制备空间位阻吩嗪提供了机会。由此产生的基于吩嗪的热激活延迟荧光 (TADF) 材料表现出从绿色到红色的发射带，具有高量子产率和中等荧光寿命作为固体薄膜。
• Pseudomonas fluorescens Showing Antifungal Activity against Macrophomina phaseolina, a Severe Pathogenic Fungus of Soybean, Produces Phenazine as the Main Active Metabolite
  作者：Stefany Castaldi、Marco Masi、Francisco Sautua、Alessio Cimmino、Rachele Isticato、Marcelo Carmona、Angela Tuzi、Antonio Evidente

  DOI：10.3390/biom11111728

  日期：——

  Pseudomonas fluorescens 9 and Bacillus subtilis 54, proposed as biofungicides to control Macrophomina phaseolina, a dangerous pathogen of soybean and other crops, were grown in vitro to evaluate their ability to produce metabolites with antifungal activity. The aim of the manuscript was to identify the natural compounds responsible for their antifungal activity. Only the culture filtrates of P. fluorescens 9 showed strong antifungal activity against M. phaseolina. Its organic extract contained phenazine and mesaconic acid (1 and 2), whose antifungal activity was tested against M. phaseolina, as well as Cercospora nicotianae and Colletotrichum truncatum, other pathogens of soybean; however, only compound 1 exhibited activity. The antifungal activity of compound 1 was compared to phenazine-1-carboxylic acid (PCA, 3), 2-hydroxyphenazine (2-OH P, 4), and various semisynthetic phenazine nitro derivatives in order to perform a structure–activity relationship (SAR) study. PCA and phenazine exhibited the same percentage of growth inhibition in M. phaseolina and C. truncatum, whereas PCA (3) showed lower activity against C. nicotianae than phenazine. 2-Hydroxyphenazine (4) showed no antifungal activity against M. phaseolina. The results of the SAR study showed that electron attractor (COOH and NO2) or repulsor (OH) groups significantly affect the antifungal growth, as well as their α- or β-location on the phenazine ring. Both PCA and phenazine could be proposed as biopesticides to control the soybean pathogens M. phaseolina, C. nicotianae, and C. truncatum, and these results should prompt an investigation of their large-scale production and their suitable formulation for greenhouse and field applications.

  Pseudomonas fluorescens 9和Bacillus subtilis 54被提议作为生物杀菌剂，用于控制大豆和其他作物的危险病原体Macrophomina phaseolina。为了评估它们产生具有抗真菌活性的代谢物的能力，在体外培养了这些细菌。本文的目的是确定其抗真菌活性的自然化合物。只有P. fluorescens 9的培养滤液显示出对M. phaseolina的强烈抗真菌活性。其有机提取物含有苯肼和丙酮酸（1和2），对M. phaseolina、Cercospora nicotianae和Colletotrichum truncatum等大豆病原体的抗真菌活性进行了测试，但只有化合物1表现出活性。将化合物1的抗真菌活性与苯肼-1-羧酸（PCA，3）、2-羟基苯肼（2-OH P，4）以及各种半合成苯肼硝基衍生物进行比较，以进行结构-活性关系（SAR）研究。PCA和苯肼在M. phaseolina和C. truncatum中显示出相同的生长抑制百分比，而PCA（3）对C. nicotianae的活性低于苯肼。2-羟基苯肼（4）对M. phaseolina没有抗真菌活性。SAR研究的结果表明，电子吸引剂（COOH和NO2）或排斥剂（OH）基团显着影响抗真菌生长，以及它们在苯肼环上的α或β位置。PCA和苯肼都可以作为生物杀虫剂，用于控制大豆病原体M. phaseolina、C. nicotianae和C. truncatum，这些结果应促使对它们的大规模生产和适合温室和田间应用的适当配方进行研究。
• Fasani, Elisa; Amer, Atef M.; Albini, Angelo, Heterocycles, 1994, vol. 37, # 2, p. 985 - 992
  作者：Fasani, Elisa、Amer, Atef M.、Albini, Angelo

  DOI：——

  日期：——
• Grabenko; Serebrjanyi, Ukrainskij Khimicheskij Zhurnal, 1955, vol. 21, p. 249,250
  作者：Grabenko、Serebrjanyi

  DOI：——

  日期：——

表征谱图