10-硝基-10h-蒽-9-酮 | 6313-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 10-硝基-10h-蒽-9-酮
• 中文别名: 3,4-二溴-4-苯基-2-丁酮；10-硝基蒽酮
• 英文名称: 9-nitroanthrone
• 英文别名: 10-Nitro-anthron；9-Nitro-anthron；10-nitro-anthrone；10-Nitro-9-oxo-anthracen-dihydrid-(9.10)；10-nitro-9(10H)-anthracenone；10-Nitroanthracen-9(10h)-one；10-nitro-10H-anthracen-9-one
• CAS: 6313-44-6
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: UWLBXNSHGLMXLU-UHFFFAOYSA-N

物化性质

• 熔点：
  136-138 °C
• 沸点：
  414.2±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2914700090

制备方法与用途

化学性质： 淡黄色针状结晶，熔点为140℃。

用途： 主要用于有机合成。

生产方法： 将20克蒽酮溶解于300毫升冰乙酸中，在60℃下搅拌，并在1小时内滴加10.5克发烟硝酸与50毫升冰乙酸的混合物。冷却至10℃后，得到约15克产品；向母液中加入水，又结晶出约6克产品。将两次获得的产品用苯-石油醚（1:1）重结晶，最终得到16.5克10-硝基蒽，收率为67%。

反应信息

• 作为反应物：
  描述：

  10-硝基-10h-蒽-9-酮 在 sodium hydroxide 、 甲基锂 、 硝酸 、 calcium carbonate 作用下， 生成 1,2-二羟基蒽醌
  参考文献：
  名称：

  DE292247

  摘要：

  公开号：
• 作为产物：
  描述：

  蒽酮 在 吡啶 、 硝酸 、 溶剂黄146 作用下， 生成 10-硝基-10h-蒽-9-酮
  参考文献：
  名称：

  Barnett; Cook, Journal of the Chemical Society, 1923, vol. 123, p. 2641

  摘要：

  DOI：

文献信息

• Enzymatic Cleavage of Aryl Acetates
  作者：Marcel Bauch、Dominique Böttcher、Uwe T. Bornscheuer、Torsten Linker

  DOI：10.1002/cctc.201600678

  日期：2016.9.7

  the cleavage of aryl acetates. Phenyl and naphthyl acetates react with lipases and esterases, whereas the sterically demanding anthracene acetate gave a conversion only with porcine liver esterase and esterase 2 from Bacillus subtilis (BS2) . These two enzymes have been employed on a preparative (0.5 mmol) scale and afforded cleavage products in 91 and 94 % yields, even for anthracene acetate. Thus

  已经筛选了七个酶来切割乙酸芳基酯。苯基乙酸萘酯和萘乙酸酯与脂肪酶和酯酶反应，而对空间要求苛刻的蒽乙酸酯仅与猪肝酯酶和枯草芽孢杆菌的酯酶2发生转化（BS2）。这两种酶已在制备型（0.5 mmol）规模上使用，即使对于乙酸蒽，也能以91％和94％的产率提供裂解产物。因此，该方法优于用催化量的甲醇钠进行化学裂解（Zemplén条件），后者的转化率很低。最后，用蒽双乙酸酯实现了区域选择性，其中乙基控制第一乙酸酯的裂解。这表明空间相互作用在乙酸芳基酯的酶促裂解中起关键作用，这对于将来的应用或酶抑制剂的开发可能是令人感兴趣的。
• US2361259
  申请人：——

  公开号：——

  公开（公告）日：——
• Gas/Solid Reactions with Nitrogen Dioxide
  作者：Gerd Kaupp、Jens Schmeyers

  DOI：10.1021/jo00122a031

  日期：1995.9

  Numerous gas/solid reactions of nitrogen dioxide with organic substrates are investigated preparatively and mechanistically. Gaseous NO2 reacts with crystalline stable free radicals (nitroxyls 1, verdazyl 6) by electron transfer. The nitrite ions formed are irreversibly oxidized by NO2 via oxygen atom transfer. Solid cation nitrates are formed quantitatively. Thione bonds of thiohydantoins 8 are transformed to carbonyl bonds with formation of sulfur and NO presumably via nitrites as intermediates. Hydantoin 13 oxygenates at its free 5-methylene group via C-H abstraction and nitrite or it undergoes N-1 nitration via N-H abstraction depending on the conditions. Both reactions proceed quantitatively. 1,3-Oxazolidin-2-one (15) gives N-nitration and N-nitrosation with the NO produced. Nonenolized crystalline barbituric acids 17 are quantitatively nitrated (C-N bond formation with radicals) at their methylene groups. 4-Hydroxybenzaldehyde (19) and vanilline (22) give quantitative aromatic nitration (C-N bond formation with arenes) without melting. All possible regioisomers are formed. Solid 9-methylanthracene (26) gives a quantitative yield of its 10-nitro derivative 27. Crystalline anthracene (28) and gaseous NO2 yield 3 primary products 29 (cis; trans) and the new dimeric product 30 as well as the stable secondary products 31 and 32. The gas/solid tetranitration of tetraphenylethylene (33) is severely hindered by the water of reaction. However, a 95% yield of pure tetrakis(p-nitrophenyl)ethylene is obtained if the drying agent MgSO4 . 2H(2)O is admired and the product 34 extracted. The gas/solid procedures avoid solvents and fuming nitric acid. They give pure products without necessity for recrystallization in most cases and they avoid wastes. Atomic force microscopy (AFM) measurements on prominent faces of single crystals of 1a, 11a, 28, and 33 reveal phase rebuildings with well-directed long-range molecular transports. Nanoliquids were only present on (110) of 28. The characteristic AFM features are correlated with known X-ray crystal structure data and compared with previous results. The shape of the features depends on the molecular packing in the crystal bulk and on the molecular shapes. Molecular interpretations of the AFM features are given.
• Barnett; Cook; Matthews, Journal of the Chemical Society, 1923, vol. 123, p. 2005
  作者：Barnett、Cook、Matthews

  DOI：——

  日期：——
• Meisenheimer; Connerade, Justus Liebigs Annalen der Chemie, 1904, vol. 330, p. 146,169
  作者：Meisenheimer、Connerade

  DOI：——

  日期：——