3-(2-Methoxy-ethyl)-5-[1-phenylamino-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one | 205309-95-1

• 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: 3-(2-Methoxy-ethyl)-5-[1-phenylamino-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one
• CAS: 205309-95-1
• 化学式: C₁₃H₁₄N₂O₂S₂
• 分子量: 294.398
• InChiKey: IHVCFSQWRBLGAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(2-Methoxy-ethyl)-5-[1-phenylamino-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one 、 1,2-dimethyl-4-(1-naphthyl)pyridinium iodide 在 乙酸酐 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以43%的产率得到3-(2-Methoxy-ethyl)-5-[2-[1-methyl-4-naphthalen-1-yl-1H-pyridin-(2E)-ylidene]-eth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and Properties of Bismerocyanines Linked by a 1,8-Naphthylene Skeleton. Novel Solvatochromism Based on Change of Intramolecular Excitonic Coupling Mode

  摘要：

  A newly prepared bismerocyanine linked by a 1,8-naphthylene skeleton has two rotational isomers, syn and anti conformers, with respect to orientation of the two merocyanine chromophores. The NMR studies revealed that a polar solvent such as acetonitrile enhanced a preference for the syn conformer to bring about much larger bathochromic shift of the UV/vis absorption band than that of a 1-naphthyl-substituted merocyanine. The INDO/S-CI calculation indicated that the UV/vis absorption bands of the syn and anti conformers are hypsochromically and bathochromically shifted, respectively, compared to that of the 1-naphthylmerocyanine. Ln accordance with the prediction based on an exciton coupling theory, the anti conformer fluoresces while the syn conformer does not. A polarographic analysis indicated a positive shift of reduction potential and a negative shift of oxidation potential compared to the corresponding value of the 1-naphthylmerocyanine. The shift in the reduction potential of the bismerocyanine relative to the 1-naphthylmerocyanine in acetonitrile was larger than those in chloroform. This was attributed to the difference in the syn/anti ratio.

  DOI：

  10.1021/ja973608p
• 作为产物：
  描述：

  3-(2-methoxy-ethyl)-2-thioxo-thiazolidin-4-one 、 N,N'-二苯甲脒 以 Petroleum ether 为溶剂， 反应 1.0h， 以81%的产率得到3-(2-Methoxy-ethyl)-5-[1-phenylamino-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and Properties of Bismerocyanines Linked by a 1,8-Naphthylene Skeleton. Novel Solvatochromism Based on Change of Intramolecular Excitonic Coupling Mode

  摘要：

  A newly prepared bismerocyanine linked by a 1,8-naphthylene skeleton has two rotational isomers, syn and anti conformers, with respect to orientation of the two merocyanine chromophores. The NMR studies revealed that a polar solvent such as acetonitrile enhanced a preference for the syn conformer to bring about much larger bathochromic shift of the UV/vis absorption band than that of a 1-naphthyl-substituted merocyanine. The INDO/S-CI calculation indicated that the UV/vis absorption bands of the syn and anti conformers are hypsochromically and bathochromically shifted, respectively, compared to that of the 1-naphthylmerocyanine. Ln accordance with the prediction based on an exciton coupling theory, the anti conformer fluoresces while the syn conformer does not. A polarographic analysis indicated a positive shift of reduction potential and a negative shift of oxidation potential compared to the corresponding value of the 1-naphthylmerocyanine. The shift in the reduction potential of the bismerocyanine relative to the 1-naphthylmerocyanine in acetonitrile was larger than those in chloroform. This was attributed to the difference in the syn/anti ratio.

  DOI：

  10.1021/ja973608p