2-{3-[2-(4-chlorophenyl)-2-oxoethyl]-4-oxo-2-thiazolidinylidene}acetonitrile | 887279-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-{3-[2-(4-chlorophenyl)-2-oxoethyl]-4-oxo-2-thiazolidinylidene}acetonitrile
• 英文别名: (2Z)-2-[3-[2-(4-chlorophenyl)-2-oxoethyl]-4-oxo-1,3-thiazolidin-2-ylidene]acetonitrile
• CAS: 887279-57-4
• 化学式: C₁₃H₉ClN₂O₂S
• 分子量: 292.746
• InChiKey: MAOMWLJWNSSSLN-ACAGNQJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  86.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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-(dimethylamino)phenyl]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
• 作为产物：
  描述：

  2-cyanomethylene-5H-thiazolidin-4-one 、 2'-溴-4-氯苯乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以68%的产率得到2-{3-[2-(4-chlorophenyl)-2-oxoethyl]-4-oxo-2-thiazolidinylidene}acetonitrile
  参考文献：
  名称：

  吡咯并[2,1-b]噻唑的新方法

  摘要：

  制备了5-芳酰基-2-(二甲基氨基)亚甲基-2,3-二氢-3-氧代吡咯并[2,1-b]噻唑-7-羧酸酯、-7-腈和相应的7-杂芳基取代衍生物。因此，取代的乙腈（XCH 2 CN，其中 X = CO 2 R，CN，杂芳基）用巯基乙酸处理，产生 2-(X-亚甲基)噻唑烷-4-酮，其用苯酰溴进行 N-烷基化。用过量的DMF.POCl 3 络合物对所得化合物进一步甲酰化产生上述吡咯并[2,1-b]噻唑。

  DOI：

  10.1055/s-2003-42451

文献信息

• A Novel Approach to Pyrrolo[2,1-<i>b</i>]thiazoles
  作者：Anton V. Tverdokhlebov、Elizaveta V. Resnyanska、Andrey A. Tolmachev、Alexander P. Andrushko

  DOI：10.1055/s-2003-42451

  日期：——

  5-Aroyl-2-(dimethylamino)methylidene-2,3-dihydro-3-oxopyrrolo[2,1-b]thiazole-7-carboxylic acid esters, -7-carbonitriles and corresponding 7-hetaryl substituted derivatives were prepared. Thus, the substituted acetonitriles (XCH 2 CN, where X = CO 2 R, CN, hetaryl) were treated with mercaptoacetic acid yielding 2-(X-methylidene)thiazolidin-4-ones, which were N-alkylated with phenacyl bromides. Further

  制备了5-芳酰基-2-(二甲基氨基)亚甲基-2,3-二氢-3-氧代吡咯并[2,1-b]噻唑-7-羧酸酯、-7-腈和相应的7-杂芳基取代衍生物。因此，取代的乙腈（XCH 2 CN，其中 X = CO 2 R，CN，杂芳基）用巯基乙酸处理，产生 2-(X-亚甲基)噻唑烷-4-酮，其用苯酰溴进行 N-烷基化。用过量的DMF.POCl 3 络合物对所得化合物进一步甲酰化产生上述吡咯并[2,1-b]噻唑。
• 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.