N-[(1E,3E)-5-(1,3-dimethyl-2,4,6-trioxo-1,2,3,4,5,6-hexahydropyrimidin-5-ylidene)penta-1,3-dien-1-yl]-N-phenylacetamide | 943923-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(1E,3E)-5-(1,3-dimethyl-2,4,6-trioxo-1,2,3,4,5,6-hexahydropyrimidin-5-ylidene)penta-1,3-dien-1-yl]-N-phenylacetamide
• 英文别名: N-phenyl-N-[(1E,3E)-5-(1,3-dimethyl-2,4,6-trioxohexahydro-5-pyrimidinylidene)-1,3-pentadienyl]acetamide
• CAS: 943923-90-8
• 化学式: C₁₉H₁₉N₃O₄
• 分子量: 353.378
• InChiKey: ROBMLSMKZRPQLK-BHHNFLQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  78.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[(1E,3E)-5-(1,3-dimethyl-2,4,6-trioxo-1,2,3,4,5,6-hexahydropyrimidin-5-ylidene)penta-1,3-dien-1-yl]-N-phenylacetamide 、 1-benzyl-2-methylbenzo[cd]indol-1-ium tetrafluoroborate 在 sodium acetate 、 乙酸酐 作用下， 反应 0.08h， 以18%的产率得到5-[(2E,4E,6E)-6-(1-benzylbenzo[cd]indol-2(1H)-ylidene)hexa-2,4-dien-1-ylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Synthesis, structure, and solvatochromism of merocyanine dyes based on barbituric acid

  摘要：

  Di-, tetra-, and hexamethinemerocyanines were synthesized on the basis of barbituric and 1,3-dimethylbarbituric acids and heterocycles characterized by a strong (1-benzyl-1,2-dihydrobenzo[cd]indole), medium (1,3-dihydro-1,3,3-trimethyl-2H-indole and 3-ethyl-2,3-dihydro-1,3-benzothiazole), and strong electron-donor power (1,3-diphenyl-2,3-dihydro-1H-benzirnidazole). Their solvatochromic properties were analyzed using both conventional parameters (absorption maxima and molar absorption coefficients) and centroids, oscillator strengths, widths, asymmetry and excess coefficients, and fine structure of the long-wave absorption bands, which were determined by mathematical processing (method of moments). A combination of these parameters unambiguously characterizes limiting electronic states of merocyanines (neutral polyene, polymethine, or charged polyene) responsible for the type of solvatochronism. Relations were found between solvatochromic properties, on the one hand, and donor-acceptor power of the terminal groups, length of the polymethine chain, and solvent nature, on the other. The difference in solvatochromism (up to reversal of sign) of merocyanines derived from barbituric acid and their analogs based on 1,3-dimethylbarbituric acid originates from both the difference in their electronic asymmetry and the ability of the NH groups in the former to participate in hydrogen bonding with proton-acceptor solvents.

  DOI：

  10.1134/s1070363206090167
• 作为产物：
  描述：

  5,5-二甲基丙二酰脲 、 (5-anilino-2,4-pentadienylidene)anilinium chloride 在 乙酸酐 作用下， 以53%的产率得到N-[(1E,3E)-5-(1,3-dimethyl-2,4,6-trioxo-1,2,3,4,5,6-hexahydropyrimidin-5-ylidene)penta-1,3-dien-1-yl]-N-phenylacetamide
  参考文献：
  名称：

  Influence of the Sign of Solvatochromism of Merocyanines on their Photoelectric Properties in Polymer Films

  摘要：

  DOI：

  10.1023/b:japs.0000049621.08104.86