9-Chloro-10-nitroanthracene | 66670-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-Chloro-10-nitroanthracene
• CAS: 66670-30-2
• 化学式: C₁₄H₈ClNO₂
• 分子量: 257.676
• InChiKey: DUOSABFMBRDXJW-UHFFFAOYSA-N

物化性质

• 沸点：
  433.0±25.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-Chloro-10-nitroanthracene 生成 10-Chloro-10-nitroso-10H-anthracen-9-one
  参考文献：
  名称：

  Galliani,G.; Rindone,B., Gazzetta Chimica Italiana, 1977, vol. 107, p. 435 - 436

  摘要：

  DOI：
• 作为产物：
  描述：

  蒽 在 硝酸 、 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 生成 9-Chloro-10-nitroanthracene
  参考文献：
  名称：

  Novel aromatic–polyamine conjugates as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase

  摘要：

  Three types of aromatic-polyamine conjugates (6a-6s) were designed, synthesized and evaluated as potential inhibitors for cholinesterases (ChEs). The results showed that anthraquinone-polyamine conjugates (AQPCs) exhibited the most potent acetylcholinesterase (AChE) inhibitory activity with IC50 values from 1.50 to 11.13 mu M. Anthracene-polyamine conjugates (APCs) showed a surprising selectivity (from 76- to 3125-fold) and were most potent at inhibiting butyrylcholinesterase (BChE), with IC50 values from 0.016 to 0.657 mu M. A Lineweaver-Burk plot and molecular modeling studies indicated that the representative compounds, 6l and 6k, targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of ChEs. Furthermore, APCs did not affect HepG2 cell viability at the concentration of 100 mu M. Consequently, these polyamine conjugates could be thoroughly and systematically studied for the treatment of AD. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.045

文献信息

• Sulphuryl chloride as an electrophile. Part 5. Chlorination of some anthracene derivatives; molecular orbital modelling of substituent effects
  作者：Roger Bolton、D. Brynn Hibbert、Simin Parand

  DOI：10.1039/p29860000981

  日期：——

  The rates of electrophilic attack at C-10 of some 9-substituted anthracenes (9-H, Br, CHO, CN, NO2, OMe, or Bz) by sulphuryl chloride have been measured (in PhCl 298 K). The substituent effects roughly parallel those expected from considering the simpler p-XC6H4 system (ρ–1.51; r 0.975); better agreement (ρ–1.23 ± 0.05; r 0.994) comes by using Dewar's FMMF treatment. MNDO calculations of the energy

  已经测量了一些硫磺酰氯在C-10处对C的亲电进攻速率（9-H，Br，CHO，CN，NO 2，OMe或Bz）（在PhCl 298 K中）。取代基的影响大致与考虑使用更简单的p -XC 6 H 4体系（ρ-1.51；r 0.975）有关。通过使用杜瓦氏FMMF处理可获得更好的一致性（ρ–1.23±0.05; r 0.994）。MNDO对中间σ复合物的能量和最优化几何结构的MNDO计算显示出折叠结构，其允许一定程度的sp 3C-10原子的特征，同时在蒽离子中保持扩展的π系统足够的离域。遵循Bell-Eyring-Polyani原理，每种反应物与其σ络合物之间的计算能量差与Clδ +攻击过程中实验观察到的自由能变化之间存在线性关系。
• The Reaction of Iodine Monochloride with Polycyclic Aromatic Compounds: Polar and Electron Transfer Pathways
  作者：Dean E. Turner、Robert F. O'Malley、Dennis J. Sardella、Lucio S. Barinelli、Pushkar Kaul

  DOI：10.1021/jo00103a026

  日期：1994.12

  Several polycyclic aromatic hydrocarbons were treated with iodine monochloride. Although iodination is the predominant reaction of benzenoid arenes, chlorination is the sole reaction with anthracene, phenanthrene and naphthalene compounds (except for 5), whose oxidation half-wave potentials are less than 1.58 V vs Ag/Ag+ (0.1 M). Arenes with higher potentials are unreactive. Naphthalene (9) and its derivatives with mild electron-withdrawing substituents are chlorinated; the exception (5) yields the 1-iodo product (21). The reaction is first order in substrate and second order in ICl. An electron transfer pathway involving radical cation intermediates is assumed. Ion-pair collapse of the radical cation-ICl intermediates is proposed for the chlorinations and radical-pair collapse for the iodination.