1-(2-硝基苯基)-2-苯基乙烷-1,2-二酮 | 35010-10-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(2-硝基苯基)-2-苯基乙烷-1,2-二酮
• 英文名称: 1-(2-nitrophenyl)-2-phenylethane-1,2-dione
• 英文别名: 2-Nitro-benzil；nitrobenzil；2-Nitrobenzil；o-Nitrobenzil；Nitrobenzile
• CAS: 35010-10-7
• 化学式: C₁₄H₉NO₄
• 分子量: 255.23
• InChiKey: JIGQDVLEFZZETB-UHFFFAOYSA-N

物化性质

• 熔点：
  100 °C(Solv: ethanol (64-17-5))
• 沸点：
  437.2±28.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-硝基苯基)-2-苯基乙烷-1,2-二酮 在 盐酸羟胺 作用下， 生成 2-nitro-benzil-α'-oxime
  参考文献：
  名称：

  List, Chemische Berichte, 1893, vol. 26, p. 2452

  摘要：

  DOI：
• 作为产物：
  描述：

  苄基三苯基氯化膦 在 potassium permanganate 、 正丁基锂 、 magnesium sulfate 作用下， 以 甲苯 为溶剂， 反应 75.25h， 生成 1-(2-硝基苯基)-2-苯基乙烷-1,2-二酮
  参考文献：
  名称：

  Aitken, R. Alan; Cadogan, J. I. G.; Gosney, Ian, Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 101, # 1-4, p. 281 - 286

  摘要：

  DOI：

文献信息

• Mild Oxidation of Diarylacetylenes to 1,2-Diketones Using Oxone in Trifluoroacetic Acid
  作者：Ming-Jung Wu、Jean-Ho Chu、Yen-Ju Chen

  DOI：10.1055/s-0029-1216800

  日期：2009.7

  A variety of 1,2-diaryldiketones were synthesized in 15-90% yields by treatment of diarylacetylenes with Oxone as the oxidant in trifluoroacetic acid. Oxidation of 1-nitro-2-(phenylethynyl)benzene and 2,4′-(ethyne-1,2-diyl)bis(nitrobenzene) furnished 1-benzoylbenzo[c]isoxazol-3(1H)-one and benzo[c]isoxazol-3-yl(4-nitrophenyl)methanone as the major products, respectively.

  通过在三氟乙酸中用Oxone作为氧化剂处理芳烃炔烃，合成了多种1,2-二芳基二酮，产率在15%到90%之间。对1-硝基-2-(苯乙炔)苯和2,4′-(乙炔-1,2-二基)双(硝基苯)的氧化反应分别产生了1-苯甲酰苯并[c]异噁唑-3(1H)-酮和苯并[c]异噁唑-3-基(4-硝基苯基)甲酮作为主要产物。
• A New General Approach for the Synthesis of 2-Substituted-3<i>H</i>-indol-3-one <i>N</i>-Oxide Derivatives
  作者：Vania Bernardes Génisson、Anne-Valérie Bouniol、Françoise Nepveu

  DOI：10.1055/s-2001-13368

  日期：——

  2-aryl (phenyl, 1,3-benzodioxolyl) and 2-alkyl (ethyl, sec-butyl)-3H-indol-3-one N-oxides were synthesized by a new general method involving a reductive intramolecular cyclization reaction of ortho-diketo nitrobenzene derivatives.

  2-芳基（苯基，1,3-苯并间二氧杂环戊烯基）和2-烷基（乙基，仲丁基）-3H-吲哚-3-酮N-氧化物通过涉及邻位的还原分子内环化反应的新通用方法合成二酮硝基苯衍生物。
• Process for producing benzylamines
  申请人：IHARA CHEMICAL INDUSTRY Co., Ltd.

  公开号：EP0452952A1

  公开（公告）日：1991-10-23

  A process for producing a benzylamine which comprises reacting a benzyl halide with an aqueous ammonia solution in the presence of an aromatic aldehyde represented by the formula: wherein R represents a hydrogen atom, a halogen atom or a lower alkyl group, and n is 1 or 2, separating an oily substance from the reaction mixture, and treating the oily substance with a mineral acid.

  一种生产苄胺的工艺，包括使苄基卤化物与氨水溶液在由式......表示的芳香醛存在下反应： 其中 R 代表氢原子、卤素原子或低级烷基，n 为 1 或 2，从反应混合物中分离出油性物质，并用矿物酸处理油性物质。
• Tatsugi, Jiro; Izawa, Yasuji, Journal of Chemical Research, Miniprint, 1988, # 11, p. 2747 - 2763
  作者：Tatsugi, Jiro、Izawa, Yasuji

  DOI：——

  日期：——
• Synthesis and Antiplasmodial Activity of New Indolone <i>N</i>-Oxide Derivatives
  作者：Françoise Nepveu、Sothea Kim、Jeremie Boyer、Olivier Chatriant、Hany Ibrahim、Karine Reybier、Marie-Carmen Monje、Severine Chevalley、Pierre Perio、Barbora H. Lajoie、Jalloul Bouajila、Eric Deharo、Michel Sauvain、Rachida Tahar、Leonardo Basco、Antonella Pantaleo、Francesco Turini、Paolo Arese、Alexis Valentin、Eloise Thompson、Livia Vivas、Serge Petit、Jean-Pierre Nallet

  DOI：10.1021/jm901300d

  日期：2010.1.28

  A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), its well as for cytotoxic concentration (CC50) on MCF7 and KB human tumor Cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (< 3 nM on FcB1 and = 1.7 nM on 3D7) with a very satisfactory selectivity index (CC50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day.