9-nitrobenzanthrone | 38156-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9-nitrobenzanthrone
• 英文别名: 9-nitro-benz[de]anthracen-7-one；9-Nitro-benz[de]anthracen-7-on；9-Nitro-7h-benzo[de]anthracen-7-one；9-nitrobenzo[a]phenalen-7-one
• CAS: 38156-99-9
• 化学式: C₁₇H₉NO₃
• 分子量: 275.263
• InChiKey: JLDKLCWHMUFRSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  515.8±29.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘-5-硝基苯甲酸甲酯 在 lithium hydroxide 、 三氯化铝 、 氯化亚砜 、 铜 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 9-nitrobenzanthrone
  参考文献：
  名称：

  Synthesis and Characterization of Some Nitrobenzanthrones: Suspected New Mutagens in Atmospheric Environment

  摘要：

  通过改良的乌尔曼交叉耦合反应合成了五种单硝基、三种双硝基和一种三硝基苯蒽酮，这些反应是将硝基取代的1-碘萘与甲基2-碘苯甲酸酯进行反应，随后对生成的2-(1-萘基)苯甲酸衍生物进行弗里德尔-克拉夫茨环合。

  DOI：

  10.1055/s-1997-1352

文献信息

• Reaction of Benzanthrone (7<i>H</i>-Benz[<i>d</i>,<i>e</i>]anthracen-7-one) with Nitrogen Dioxide Alone or in Admixture with Ozone. Implications for the Atmospheric Formation of Genotoxic 3-Nitrobenzanthrone
  作者：Takeji Enya、Hitomi Suzuki、Yoshiharu Hisamatsu

  DOI：10.1246/bcsj.71.2221

  日期：1998.9

  The reaction of benzanthrone (7H-benz[d,e]anthracen-7-one, 1) with nitrogen dioxide alone or in admixture with ozonized oxygen has been investigated in polar and nonpolar organic solvents at different temperatures. A remarkable change of product distribution was observed depending on the solvent employed; 3-nitrobenzanthrone (4) was the main product from the reaction in dichloromethane, while 2-nitrobenzanthrone

  苯并蒽酮 (7H-benz[d,e]anthracen-7-one, 1) 与二氧化氮单独或与臭氧化氧混合的反应已在极性和非极性有机溶剂中在不同温度下进行了研究。根据所使用的溶剂，观察到产物分布的显着变化；3-硝基苯蒽酮 (4) 是二氯甲烷中反应的主要产物，而 2-硝基苯蒽酮是四氯甲烷中的主要产物。发现加入质子酸或无机固体载体可促进反应，有利于前者硝基化合物的形成，而后者则以牺牲为代价。确定了所有主要产品。
• 230. Synthesis of mesobenzanthrones and anthanthrones by the ullmann method
  作者：H. Gordon Rule、F. Randall Smith

  DOI：10.1039/jr9370001096

  日期：——
• 3-Nitrobenzanthrone, a Powerful Bacterial Mutagen and Suspected Human Carcinogen Found in Diesel Exhaust and Airborne Particulates
  作者：Takeji Enya、Hitomi Suzuki、Tetsushi Watanabe、Teruhisa Hirayama、Yoshiharu Hisamatsu

  DOI：10.1021/es961067i

  日期：1997.10.1

  9-Nitrobenzanthrone (3-nitro-7H-benz[d,e]anthracen-7-one) was isolated from the organic extracts of both diesel exhaust and airborne particles and was identified as a new class of powerful direct mutagen. its mutagenicity by Ames Salmonella assay is very high (208 000 revertants/nmol in Salmonella typhimurium TA98 and 6 290 000 revertants/nmol in YG1024) and compares with that of 1,8-dinitropyrene, which is the direct mutagen of strongest activity (257000 revertants/nmol in TA98 and 4 780 000 revertants/nmol in YG1024) so far reported in the literature. The new mutagen was also shown to induce micronuclei in mouse peripheral blood reticulocytes after intraperitoneal administration (micronucleated reticulocytes, 0.64% against 25 mg/kg dose after 48 h), suggesting its potential genotoxicity to mammalians. 3-Nitrobenzanthrone is most likely to be formed nor only during the combustion process of fossil fuels but also from the atmospheric reaction between benzanthrone and lower oxides of: nitrogen, since the latter ketone was found to be nitrated guile easily under an artificial atmosphere containing gaseous NO2(10 ppm) and O-3 (5 ppm)to produce the powerfully mutagenic 3-nitro derivative as the major product, along with several other isomeric mononitrobenzanthrones and dinitro descendants as minor products.