2,4,6-trinitrophenylacetophenone | 35113-74-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,4,6-trinitrophenylacetophenone
• 英文别名: 1-Benzoylmethyl-2,4,6-trinitrobenzol；2',4',6'-trinitro-deoxybenzoin；2',4',6'-Trinitro-desoxybenzoin；1-Phenyl-2-(2,4,6-trinitrophenyl)ethanone
• CAS: 35113-74-7
• 化学式: C₁₄H₉N₃O₇
• 分子量: 331.241
• InChiKey: LQNADNUSVLBINS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  155
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,4,6-trinitrophenylacetophenone 在 四甲基氢氧化铵 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成
  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：

  eqimolar complex of 2,4,6-trinitrochlorobenzene with naphthalene 在 sodium ethanolate 作用下， 生成 2,4,6-trinitrophenylacetophenone
  参考文献：
  名称：

  Kimura, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 1216

  摘要：

  DOI：

文献信息

• Atroshchenko, Yu.M.; Akhromushkina, I.M.; Gitis, S.S., Russian Journal of Organic Chemistry, 1993, vol. 29, # 9.2, p. 1525 - 1531
  作者：Atroshchenko, Yu.M.、Akhromushkina, I.M.、Gitis, S.S.、Golopolosowa, T.V.、Savinova, L.N.、et al.

  DOI：——

  日期：——
• Unexpected route to 3-substituted 4,6-dinitroanthranils by oxidation of anionic ?-complexes of 1,3,5-trinitrobenzene
  作者：S. V. Kovalenko、G. A. Artamkina、P. B. Terent'ev、V. K. Shevtsov、I. P. Beletskaya、O. A. Reutov

  DOI：10.1007/bf00472561

  日期：1990.3
• KOVALENKO, S. V.;ARTAMKINA, G. A.;TERENTEV, P. B.;SHEVTSOV, V. K.;BELETSK+, XIMIYA GETEROTSIKL. SOED.,(1990) N, S. 412-416
  作者：KOVALENKO, S. V.、ARTAMKINA, G. A.、TERENTEV, P. B.、SHEVTSOV, V. K.、BELETSK+

  DOI：——

  日期：——
• IZV. AN CCCP. CEP. XIM.,(1987) N 12, 2869-2870
  作者：

  DOI：——

  日期：——