4-(4-Chloro-phenyl)-5-cyano-2-oxo-6-thioxo-1,2,3,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester | 213883-28-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 4-(4-Chloro-phenyl)-5-cyano-2-oxo-6-thioxo-1,2,3,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
• CAS: 213883-28-4
• 化学式: C₁₅H₁₁ClN₂O₃S
• 分子量: 334.783
• InChiKey: LVXAVJBLPOCBOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.19
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(4-Chloro-phenyl)-5-cyano-2-oxo-6-thioxo-1,2,3,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 在 氢氧化钾 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  REACTIONS OF α-THIOCARBOXAMIDOCINNA-MONITRILE DERIVATIVES WITH DIETHYL MALONATE: SYNTHESIS OF PYRAZOLO-[3,4-b]-α-PYRIDINONE, THIENO[2,3-b]-α-PYRIDINONE, PYRIDO[2,3:4′,5′]THIENO[2,3-c]PYRIDAZINE AND PYRIDO[2,3:4′,5′]-THIENO[2,3-d]PYRIMIDINONETHIONE DERIVATIVES

  摘要：

  3-Cyano-4-aryl-5-ethoxycarbonyl-6-pyridinone-2-thione derivatives 3a-c reacted with several halogen-containing compounds to give the corresponding 2-S-methylpyridinones 4a-c, 2-S-acetonyl pyridinones 7a-c, 2-S-benzoyl methyl pyridinones 12a-c, 2-S-acetamidopyridinones 15a-c and 2-S-ethoxycarbonyl methylpyridinones 20a-c. The ethanolic solution of KOH used as a cyclization agent to give the corresponding thieno[2,3-b]pyridines 8a-c, 13a-c, 16a-c and 21a-c. Hydrazine hydrate, nitrous acid, carbon disulphide, acetic anhydride, formic acid, acetic acid and acetyl acetone gave further cyclization to construct an additional ring.

  DOI：

  10.1080/10426509708031587
• 作为产物：
  描述：

  2-cyano-3-(4-chlorophenyl)-prop-2-enethioamide 、 丙二酸二乙酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以74%的产率得到4-(4-Chloro-phenyl)-5-cyano-2-oxo-6-thioxo-1,2,3,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  REACTIONS OF α-THIOCARBOXAMIDOCINNA-MONITRILE DERIVATIVES WITH DIETHYL MALONATE: SYNTHESIS OF PYRAZOLO-[3,4-b]-α-PYRIDINONE, THIENO[2,3-b]-α-PYRIDINONE, PYRIDO[2,3:4′,5′]THIENO[2,3-c]PYRIDAZINE AND PYRIDO[2,3:4′,5′]-THIENO[2,3-d]PYRIMIDINONETHIONE DERIVATIVES

  摘要：

  3-Cyano-4-aryl-5-ethoxycarbonyl-6-pyridinone-2-thione derivatives 3a-c reacted with several halogen-containing compounds to give the corresponding 2-S-methylpyridinones 4a-c, 2-S-acetonyl pyridinones 7a-c, 2-S-benzoyl methyl pyridinones 12a-c, 2-S-acetamidopyridinones 15a-c and 2-S-ethoxycarbonyl methylpyridinones 20a-c. The ethanolic solution of KOH used as a cyclization agent to give the corresponding thieno[2,3-b]pyridines 8a-c, 13a-c, 16a-c and 21a-c. Hydrazine hydrate, nitrous acid, carbon disulphide, acetic anhydride, formic acid, acetic acid and acetyl acetone gave further cyclization to construct an additional ring.

  DOI：

  10.1080/10426509708031587