5-(4-chlorophenyl)carbonyl-2-(4-methoxyphenyl)meth-(Z)-ylidene-3-oxo-2,3-dihydropyrrolo[2,1-b]thiazole-7-carbonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-chlorophenyl)carbonyl-2-(4-methoxyphenyl)meth-(Z)-ylidene-3-oxo-2,3-dihydropyrrolo[2,1-b]thiazole-7-carbonitrile
• 英文别名: (2Z)-5-(4-chlorobenzoyl)-2-[(4-methoxyphenyl)methylidene]-3-oxopyrrolo[2,1-b][1,3]thiazole-7-carbonitrile
• 化学式: C₂₂H₁₃ClN₂O₃S
• 分子量: 420.876
• InChiKey: CKXDRIYIXJULSE-GRSHGNNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-{3-[2-(4-chlorophenyl)-2-oxoethyl]-4-oxo-2-thiazolidinylidene}acetonitrile 在 哌啶 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-chlorophenyl)carbonyl-2-(4-methoxyphenyl)meth-(Z)-ylidene-3-oxo-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

文献信息

• Synthesis of Pyrrolo[2,1-b]thiazol-3-one Derivatives
  作者：Anton V. Tverdokhlebov、Alexander P. Andrushko、Andrey A. Tolmachev、Alexander N. Kostyuk、Alexander N. Chernega、Eduard B. Rusanov

  DOI：10.1007/s00706-005-0356-1

  日期：2005.10

  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.