(噌啉-3-基)(4-硝基苯基)甲酮 | 337512-20-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (噌啉-3-基)(4-硝基苯基)甲酮
• 英文名称: 3-(4-nitrobenzoyl)cinnoline
• 英文别名: 3-p-nitrobenzoylcinnoline；(cinnolin-3-yl)(4-nitrophenyl)methanone；Cinnolin-3-yl-(4-nitrophenyl)methanone
• CAS: 337512-20-6
• 化学式: C₁₅H₉N₃O₃
• 分子量: 279.255
• InChiKey: VEOLABGLWCEPCK-UHFFFAOYSA-N

物化性质

• 熔点：
  214-216 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  521.1±56.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-甲基苯肼盐酸盐 、 (噌啉-3-基)(4-硝基苯基)甲酮 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 4.5h， 以51%的产率得到3-(4-nitrophenyl)-1-p-tolyl-1H-pyrazolo[4,3-c]cinnoline
  参考文献：
  名称：

  A New Cyclization to Fused Pyrazoles Tunable for Pericyclic or Pseudopericyclic Route: An Experimental and Theoretical Study

  摘要：

  2-Pyrazinyl (2) and 3-pyridazinylketone arylhydrazones (6) and their benzologues undergo a ring closure reaction to yield pyrazolo[3,4-b]pyrazines (4) and pyrazolo[4,3-c]pyridazines (7), respectively, in acceptable to good yields. The reaction was found to be accelerated by using acidic or basic conditions. Quantum chemical calculations suggest the key step of the mechanism to be a direct cyclization; analysis of aromaticity based on computed magnetic properties revealed its medium-dependent pericyclic or pseudopericyclic character. The cyclization reaction has also been extended for the synthesis of related ring systems (9, 12, 14).

  DOI：

  10.1021/jo800483a
• 作为产物：
  描述：

  3-(4-nitrophenyl)-3-oxo-2-(phenylhydrazono)propionaldehyde 在 硫酸 作用下， 反应 0.08h， 以60%的产率得到(噌啉-3-基)(4-硝基苯基)甲酮
  参考文献：
  名称：

  从芳基甲基酮高效合成3-芳基肉桂啉

  摘要：

  描述了从合适的芳基甲基酮开始的3-芳基肉桂啉的有效合成。将后者分两步转化为相应的3-氧代-3-芳基-2-芳基肼基丙醛，其在浓盐酸中经酸催化环化。硫酸或多磷酸（PPA）生成相应的3-aroylcinnolines。

  DOI：

  10.1016/s0040-4020(00)01141-8

文献信息

• Catalyst-Free Cascade Annulation of Enaminones and Aryl Diazonium Tetrafluoroboronates for Cinnoline Synthesis and the Anti-Inflammatory Activity Study
  作者：Shanghui Tian、Yunyun Liu、Changfeng Wan、Jie-Ping Wan、Guifeng Hao

  DOI：10.1021/acs.joc.2c02858

  日期：2023.2.17

  A simple and concise method for the synthesis of cinnolines has been developed by the reactions of readily available enaminones and aryl diazonium tetrafluoroboronates. The reactions run efficiently to provide cinnolines with broad diversity in the substructure by heating in dimethyl sulfoxide without using any catalyst or additive. In addition, the primary investigation of the anti-inflammatory activity

  通过容易获得的烯胺酮和芳基四氟硼酸重氮盐的反应，开发了一种简单明了的合成肉啉的方法。在不使用任何催化剂或添加剂的情况下，通过在二甲亚砜中加热，反应可以高效运行，从而提供亚结构具有广泛多样性的肉啉。此外，对这些产品的抗炎活性的初步研究导致观察到对氯苯甲酰 ( 3f ) 和对硝基苯甲酰 ( 3j ) 肉啉作为有吸引力的体外抗炎化合物。
• Flash vacuum pyrolysis of 3-aroylcinnolines: interesting routes toward polynuclear aromatic compounds
  作者：Yehia A Ibrahim、Nouria A Al-Awadi、Kamini Kaul

  DOI：10.1016/s0040-4020(01)00577-4

  日期：2001.8

  Flash vacuum pyrolysis of 3-aroylcinnolines 3 at 900 degreesC and 0.02 Torr yielded phenanthrene and arylacetylene derivatives as the major products beside anthracene, and diarylacetylene derivatives as minor products. Also, FVP of 3-(2-thienoyl)-cinnoline gave three isomeric naphthothiophenes, phenyl-2-thienylacetylene and phenylacetylene. On the other hand, 3-(2-furoyl)-cinoline gave dibenzofuran as a major product besides naphtho[1,2-b]furan and phenylacetylene. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Efficient synthesis of 3-aroylcinnolines from aryl methyl ketones
  作者：Nouria A Al-Awadi、Mohamed Hilmy Elnagdi、Yehia A Ibrahim、Kamini Kaul、Ajith Kumar

  DOI：10.1016/s0040-4020(00)01141-8

  日期：2001.2

  An efficient synthesis of 3-aroylcinnolines starting from the appropriate aryl methyl ketones is described. The latter were converted in two steps to the corresponding 3-oxo-3-aryl-2-arylhydrazonopropanals, which upon acid catalyzed cyclization in conc. sulfuric acid or polyphosphoric acid (PPA) led to the corresponding 3-aroylcinnolines.

  描述了从合适的芳基甲基酮开始的3-芳基肉桂啉的有效合成。将后者分两步转化为相应的3-氧代-3-芳基-2-芳基肼基丙醛，其在浓盐酸中经酸催化环化。硫酸或多磷酸（PPA）生成相应的3-aroylcinnolines。
• A New Cyclization to Fused Pyrazoles Tunable for Pericyclic or Pseudopericyclic Route: An Experimental and Theoretical Study
  作者：László Filák、Tibor András Rokob、Gyöngyvér Ágnes Vaskó、Orsolya Egyed、Ágnes Gömöry、Zsuzsanna Riedl、György Hajós

  DOI：10.1021/jo800483a

  日期：2008.5.1

  2-Pyrazinyl (2) and 3-pyridazinylketone arylhydrazones (6) and their benzologues undergo a ring closure reaction to yield pyrazolo[3,4-b]pyrazines (4) and pyrazolo[4,3-c]pyridazines (7), respectively, in acceptable to good yields. The reaction was found to be accelerated by using acidic or basic conditions. Quantum chemical calculations suggest the key step of the mechanism to be a direct cyclization; analysis of aromaticity based on computed magnetic properties revealed its medium-dependent pericyclic or pseudopericyclic character. The cyclization reaction has also been extended for the synthesis of related ring systems (9, 12, 14).