2,5-dinitrophenyl benzoate | 1694-28-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2,5-dinitrophenyl benzoate
• 英文别名: 2,5-dinitrophenylbenzoate；2,5-Dinitro-phenylbenzoat
• CAS: 1694-28-6
• 化学式: C₁₃H₈N₂O₆
• 分子量: 288.216
• InChiKey: AQMRGRGHJUFVOS-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C
• 沸点：
  500.6±40.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112.58
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,5-dinitrophenyl benzoate 、 L-脯氨酸 在 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 N-苯甲酰基-l-脯氨酸
  参考文献：
  名称：

  Reactivity of Tyrosyl–Proline toward Benzoylation in Aqueous 1,4-Dioxane

  摘要：

  The kinetics of the reaction of L-tyrosyl-L-proline (Tyr-Pro) with di- and trinitrophenyl benzoates in aqueous 1,4-dioxane (40 wt % of water) were studied in the temperature range 298-313 K. The reaction rate constant k(298) was found to vary in the range from 0.035 to 0.564 L.mol(-1).s(-1), and the activation barrier changed from 39 to 51 kJ/mol. The neutral and anionic forms of the dipeptide were simulated by the DFT/B3LYP/cc-pVTZ method. Natural bond orbital analysis of the electron density distribution in these forms showed that the preferred nucleophilic center in the dipeptide molecule is the nitrogen atom of the primary amino group rather than the oxygen atom of the phenolic hydroxy group.

  DOI：

  10.1134/s1070428020060111
• 作为产物：
  描述：

  γ-二硝基酚 、 苯甲酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 2,5-dinitrophenyl benzoate
  参考文献：
  名称：

  Belousova; Simanenko; Savelova, Russian Journal of Organic Chemistry, 2000, vol. 36, # 11, p. 1656 - 1664

  摘要：

  DOI：

文献信息

• Reactivity of α-amino acids in the N-acylation with benzoic acid esters in aqueous dioxane
  作者：N. R. Ishkulova、L. E. Oparina、L. B. Kochetova、T. P. Kustova、N. V. Kalinina、L. V. Kuritsin

  DOI：10.1134/s1070363210050178

  日期：2010.5

  The effect of the nitro group as a substituent in the phenoxide part of phenyl benzoate on the rate of N-acylation of glycine, L-proline, and L-valine in the water (40 wt %)-dioxane solvent was studied. The activation parameters of glycine reactions with the esters were measured. The existence of compensation effect and the linear relation of the logarithms of the acylation constants to the Hammett constants were revealed. The energy of the LUMO of esters can serve as the descriptors of the easters reactivity.