Thiobenzoic acid S-[4-(4-chloro-phenyl)-3-morpholin-4-yl-1H-pyrrol-2-yl] ester | 183591-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Thiobenzoic acid S-[4-(4-chloro-phenyl)-3-morpholin-4-yl-1H-pyrrol-2-yl] ester
• 英文别名: S-[4-(4-chlorophenyl)-3-morpholin-4-yl-1H-pyrrol-2-yl] benzenecarbothioate
• CAS: 183591-89-1
• 化学式: C₂₁H₁₉ClN₂O₂S
• 分子量: 398.913
• InChiKey: HSBZMLWJRUEFGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  70.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Thiobenzoic acid S-[4-(4-chloro-phenyl)-3-morpholin-4-yl-1H-pyrrol-2-yl] ester 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.25h， 生成 4-[4-(4-Chloro-phenyl)-2-methylsulfanyl-1H-pyrrol-3-yl]-morpholine
  参考文献：
  名称：

  Mechanistic aspects of the synthesis of 3-aminopyrroles from substituted 2-methyl-1,2-thiazolium salts or 3-aminothioacrylamides

  摘要：

  The mechanism of the synthesis of 3-aminopyrroles 3 by ring transformation–desulfurisation of substituted 2-methyl-1,2-thiazolium salts 2 has been investigated. 3-Alkylideneaminothioacrylamides 4 and 2H-1,3-thiazines 5 could be synthesised by base treatment of 1,2-thiazolium bromides 2 and proved to be intermediates in the ring transformation–desulfurisation. Hitherto unknown bis(2-aminothiocarbonylvinyl)amines 6 are observed as by-products. When 3-phenacylaminothioacrylamide 1c is oxidised with hydrogen peroxide a novel pyrrole formation occurs to give 2-benzoylthiopyrrole 8a, where the sulfur atom is retained in the product. An erroneously reported 1,2-thiazolium-2-methanide 7 has been reassigned as 3-(4-nitrobenzylideneamino)thioacrylamide 4a on the basis of an X-ray crystal structure determination.

  DOI：

  10.1039/p19960002339
• 作为产物：
  描述：

  2-[(Z)-2-(4-Chloro-phenyl)-3-morpholin-4-yl-3-thioxo-propenylamino]-1-phenyl-ethanone 在 双氧水 作用下， 以 乙醇 为溶剂， 以70.4%的产率得到Thiobenzoic acid S-[4-(4-chloro-phenyl)-3-morpholin-4-yl-1H-pyrrol-2-yl] ester
  参考文献：
  名称：

  Mechanistic aspects of the synthesis of 3-aminopyrroles from substituted 2-methyl-1,2-thiazolium salts or 3-aminothioacrylamides

  摘要：

  The mechanism of the synthesis of 3-aminopyrroles 3 by ring transformation–desulfurisation of substituted 2-methyl-1,2-thiazolium salts 2 has been investigated. 3-Alkylideneaminothioacrylamides 4 and 2H-1,3-thiazines 5 could be synthesised by base treatment of 1,2-thiazolium bromides 2 and proved to be intermediates in the ring transformation–desulfurisation. Hitherto unknown bis(2-aminothiocarbonylvinyl)amines 6 are observed as by-products. When 3-phenacylaminothioacrylamide 1c is oxidised with hydrogen peroxide a novel pyrrole formation occurs to give 2-benzoylthiopyrrole 8a, where the sulfur atom is retained in the product. An erroneously reported 1,2-thiazolium-2-methanide 7 has been reassigned as 3-(4-nitrobenzylideneamino)thioacrylamide 4a on the basis of an X-ray crystal structure determination.

  DOI：

  10.1039/p19960002339