| 72318-42-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 72318-42-4
• 化学式: C₆H₁₅N*C₁₄H₁₀N₃O₇*H
• 分子量: 434.449
• InChiKey: CSVNIPGKRDKNKQ-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  155.72
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 以69.5%的产率得到2,4,6-trinitrophenylacetophenone
  参考文献：
  名称：

  Transition State Imbalances in the Deprotonation of Picrylacetophenones by Carboxylate and Phenoxide Bases

  摘要：

  The kinetics of the reversible deprotonation of 4-X-substituted picrylacetophenones 3a-c (X = NO2, H, MeO) by a variety of bases have been measured in 50% H(2)0-50%Me(2)SO (v/v) at 25 degrees C. Comparison of Bronsted PB values for the ionization of each carbon acid by phenoxide and carboxylate bases and alpha(CH) values for deprotonation of 3a-c by individual buffers bases indicates that the reaction proceeds through strongly imbalanced transition states. The intrinsic reactivities of 3a-c, as determined from the Bronsted plots for phenoxide ion reactions, are typical for the formation of resonance-stabilized polynitrobenzyl-type carbanions, but the intrinsic rate constant k(0) decreases regularly on going from the less acidic p-methoxyacetophenone derivative 3c to the more acidic p-nitroacetophenone derivative 3a. This trend is attributed to the fact that the contribution of the benzoyl moiety to the resonance stabilization of the resulting carbanion C-3 is completely negligible for the p-methoxy compound but not for the p-nitro compound. An extensive H-1 and C-13 NMR study of the ionization of 3a-c confirms this proposal, with steric hindrance to rotation of the picryl ring around the C-alpha-C-ipso linkage being observed at the probe temperature in the p-methoxy-substituted carbanion C-3c, at -40 degrees C for the unsubstituted carbanion C-3b, but not at all for the p-nitro carbanion C-3a. A major finding, however, is that the three carbanions undergo protonation at the p-nitro group of the picryl ring to form nitronic acids in acidic media. This behavior clearly shows that charge delocalization through the 2,4,6-trinitrophenyl moiety is predominant in the three systems, including C-3a.

  DOI：

  10.1021/jo9518617
• 作为产物：
  描述：

  1,3,5-三硝基苯 、 三乙胺 、 苯乙酮 以 乙醚 为溶剂， 反应 12.0h， 以78%的产率得到
  参考文献：
  名称：

  Stability of carbon-bonded anionic .sigma. complexes. 3. Decomposition in aqueous acidic media

  摘要：

  DOI：

  10.1021/jo01291a018