5-(2,6-dichlorobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(2,6-dichlorobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: 5-[(2,6-Dichlorophenyl)methylidene]-1,3-diazinane-2,4,6-trione
• 化学式: C₁₁H₆Cl₂N₂O₃
• mdl: MFCD00117964
• 分子量: 285.086
• InChiKey: SQYOZZVSVQWNJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2,6-dichlorobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 在 苯甲醛 、 2-氨基苯硫醇 作用下， 以 水 为溶剂， 反应 0.33h， 以0.236 g的产率得到5-(2,6-dichlorobenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  2-苯基-2,3-二氢苯并[d]噻唑：一种温和、高效、高活性的原位化学选择性还原剂，用于在水中一锅法合成 5-单烷基巴比妥酸盐

  摘要：

  使用原位生成的化学选择性还原剂 2-苯基-2,3-二氢苯并[d]噻唑从巴比妥酸和醛一锅合成 5-单烷基巴比妥酸酯的无金属和无催化剂还原烷基化方案并描述了苯甲醛。该协议的显着优点是操作简单、反应条件温和、收率高、反应时间短、后处理和纯化过程简单，使其极具吸引力。

  DOI：

  10.1055/s-0036-1591725
• 作为产物：
  描述：

  巴比妥酸 、 2,6-二氯苯甲醛 以 水 为溶剂， 反应 0.17h， 生成 5-(2,6-dichlorobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  2-苯基-2,3-二氢苯并[d]噻唑：一种温和、高效、高活性的原位化学选择性还原剂，用于在水中一锅法合成 5-单烷基巴比妥酸盐

  摘要：

  使用原位生成的化学选择性还原剂 2-苯基-2,3-二氢苯并[d]噻唑从巴比妥酸和醛一锅合成 5-单烷基巴比妥酸酯的无金属和无催化剂还原烷基化方案并描述了苯甲醛。该协议的显着优点是操作简单、反应条件温和、收率高、反应时间短、后处理和纯化过程简单，使其极具吸引力。

  DOI：

  10.1055/s-0036-1591725

文献信息

• Cremlyn, Richard; Bassin, Jatinder P.; Ahmed, Fozia, Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 73, # 1-4, p. 161 - 172
  作者：Cremlyn, Richard、Bassin, Jatinder P.、Ahmed, Fozia、Hastings, Michael、Hunt, Ian、Mattu, Tajinder

  DOI：——

  日期：——
• Synthesis, NMR, FT-IR, X-ray structural characterization, DFT analysis and isomerism aspects of 5-(2,6-dichlorobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
  作者：Assem Barakat、Hany J. Al-Najjar、Abdullah Mohammed Al-Majid、Saied M. Soliman、Yahia Nasser Mabkhot、Mohammed Rafi Shaik、Hazem A. Ghabbour、Hoong-Kun Fun

  DOI：10.1016/j.saa.2015.03.016

  日期：2015.8

  The synthesis and spectral characterization of the 5-(2,6-dichlorobenzylidene)-pyrimidine-2,4,6(1H,3H,5H)-trione;3 was reported. The solid state molecular structure of 3 was studied using X-ray crystallography. The relative stabilities of the seven possible isomers of 3 were calculated by DFT/B3LYP method using 6-311G(d,p) basis set. The calculated total energies and thermodynamic parameters were used to predict the relative stabilities of these isomers. The effect of solvent polarity on the relative stability of these isomers was studied at the same level of theory using PCM. It was found that the keto form, (TO), is the most stable isomer both in the gaseous state and solution. In solution, the calculated total energies of all isomers are decreased indicating that all isomers are stabilized by the solvent effect. The vibrational spectra of the most stable isomer, 3(TO) are calculated using the same level of theory and the results are compared with the experimentally measured FTIR spectra. Good correlation was obtained between the experimental and calculated vibrational frequencies (R-2 = 0.9992). The electronic spectra of 3(T0) in gas phase as well as in solutions were calculated using the TD-DFT method. All the predicted electronic transitions showed very little spectral shifts and increase in the intensity of absorption due to solvent effect. Also the H-1- and C-13-NMR chemical shifts of the stable isomer were calculated and the results were correlated with the experimental data. Good correlations between the experimental and calculated chemical shifts were obtained. (C) 2015 Elsevier B.V. All rights reserved.