{5-[4-(dimethylamino)phenyl]meth-(Z)-ylidene-4-oxo-3-(2-oxo-2-phenylethyl)thiazolidin-(2Z)-ylidene}acetonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {5-[4-(dimethylamino)phenyl]meth-(Z)-ylidene-4-oxo-3-(2-oxo-2-phenylethyl)thiazolidin-(2Z)-ylidene}acetonitrile
• 英文别名: (2Z)-2-[(5Z)-5-[[4-(dimethylamino)phenyl]methylidene]-4-oxo-3-phenacyl-1,3-thiazolidin-2-ylidene]acetonitrile
• 化学式: C₂₂H₁₉N₃O₂S
• 分子量: 389.478
• InChiKey: KAKUIHYGCRQAEP-VIESFARRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  89.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {5-[4-(dimethylamino)phenyl]meth-(Z)-ylidene-4-oxo-3-(2-oxo-2-phenylethyl)thiazolidin-(2Z)-ylidene}acetonitrile 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以58%的产率得到2-[4-(dimethylamino)phenyl]meth-(Z)-ylidene-3-oxo-5-phenylcarbonyl-2,3-dihydropyrrolo[2,1-b]thiazole-7-carbonitrile
  参考文献：
  名称：

  Synthesis of Pyrrolo[2,1-b]thiazol-3-one Derivatives

  摘要：

  Ethyl [4-oxo-3- (2-oxo-2-arylethyl)thiazolidin-2-ylidene] acetates and [4-oxo-3-(2-oxo-2-arylethyl)thiazolidin-2-ylidene]acetonitriles were shown to react with substituted benzaldehydes at the endocyclic methylene group leading to the corresponding 5-arylmethylidene derivatives. Their treatment with DMF center dot POCl3 complex yielded 3-oxo-5-aroyl-2-arylmethylidene-2,3-dihydropyrrolo[2,1-b]thiazole-7-carboxylic acids ethyl esters and -7-carbonitriles. The structures of the pyrrolothiazoles were confirmed by an X-ray crystallographic study, which indicated the (Z) -configuration at the arylmethylidene moiety.

  DOI：

  10.1007/s00706-005-0356-1
• 作为产物：
  描述：

  [4-Oxo-3-(2-oxo-2-phenyl-ethyl)-thiazolidin-(2Z)-ylidene]-acetonitrile 、 对二甲氨基苯甲醛 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到{5-[4-(dimethylamino)phenyl]meth-(Z)-ylidene-4-oxo-3-(2-oxo-2-phenylethyl)thiazolidin-(2Z)-ylidene}acetonitrile
  参考文献：
  名称：

  Synthesis of Pyrrolo[2,1-b]thiazol-3-one Derivatives

  摘要：

  Ethyl [4-oxo-3- (2-oxo-2-arylethyl)thiazolidin-2-ylidene] acetates and [4-oxo-3-(2-oxo-2-arylethyl)thiazolidin-2-ylidene]acetonitriles were shown to react with substituted benzaldehydes at the endocyclic methylene group leading to the corresponding 5-arylmethylidene derivatives. Their treatment with DMF center dot POCl3 complex yielded 3-oxo-5-aroyl-2-arylmethylidene-2,3-dihydropyrrolo[2,1-b]thiazole-7-carboxylic acids ethyl esters and -7-carbonitriles. The structures of the pyrrolothiazoles were confirmed by an X-ray crystallographic study, which indicated the (Z) -configuration at the arylmethylidene moiety.

  DOI：

  10.1007/s00706-005-0356-1