N-[3-(piperidine-1-carbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-yl]benzamide | 356586-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-[3-(piperidine-1-carbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-yl]benzamide
• 英文别名: N-[3-(piperidin-1-ylcarbonyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]benzamide；N-[3-(piperidine-1-carbonyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]benzamide
• CAS: 356586-88-4
• 化学式: C₂₁H₂₄N₂O₂S
• 分子量: 368.5
• InChiKey: LZFUFZZJSKHZAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯甲酰基氨基-4,5,6,7-四氢-1-苯并噻吩-3-羧酸 在 乙酸酐 作用下， 反应 5.08h， 生成 N-[3-(piperidine-1-carbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-yl]benzamide
  参考文献：
  名称：

  Synthesis of Some New Tetrahydrobenzo[b]thiophene Derivatives and Tetrahydrobenzothienopyrimidine Derivatives Under Microwave Irradiation

  摘要：

  2-Phenyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]oxazin-4-one (4) was reacted with either aliphatic or aromatic primary amines such as benzylamine, cyclohexylamine, p-toluidine, and/or p-anisidine to give carboxamide derivatives 5a-d, respectively. A bifunctional nucleophile such as ethanolamine was also reacted with 4, giving the carboxamide derivative 5e. Aminolysis of 4 with secondary amines such as piperidine and/or morpholine afforded the benzamide derivatives 6a and/or 6b, respectively. Fusion of 4 with hydrazine hydrate yielded the pyrimidine derivative 7 and carbohydrazide derivative 8. Thiation of 4 with phosphorous pentasulfide gave thienothiazine derivative 9, which reacted with benzylamine to give the pyrimidine derivative 10. Carbon nucleophiles such as ethyl cyanoacetate and/or malononitrile were subjected to react with 4 to give oxopropanoate 11 and/or oxopropanoic acid 12 derivatives, respectively. Microwave irradiation of 4 and formamide yielded the pyrimidinone derivative 13, which were subjected to react with phosphorous pentasulfide, a mixture of phosphorous oxychloride and phosphorous pentachloride and/or methyl iodide, to give 14, 15, and/or 16, respectively.

  DOI：

  10.1080/00397911.2010.501479

文献信息

• Synthesis of Some New Tetrahydrobenzo[b]thiophene Derivatives and Tetrahydrobenzothienopyrimidine Derivatives Under Microwave Irradiation
  作者：A. A. Abdalha、M. K. Abou El-Regal、M. A. El-Kassaby、A. T. Ali

  DOI：10.1080/00397911.2010.501479

  日期：2011.10

  2-Phenyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]oxazin-4-one (4) was reacted with either aliphatic or aromatic primary amines such as benzylamine, cyclohexylamine, p-toluidine, and/or p-anisidine to give carboxamide derivatives 5a-d, respectively. A bifunctional nucleophile such as ethanolamine was also reacted with 4, giving the carboxamide derivative 5e. Aminolysis of 4 with secondary amines such as piperidine and/or morpholine afforded the benzamide derivatives 6a and/or 6b, respectively. Fusion of 4 with hydrazine hydrate yielded the pyrimidine derivative 7 and carbohydrazide derivative 8. Thiation of 4 with phosphorous pentasulfide gave thienothiazine derivative 9, which reacted with benzylamine to give the pyrimidine derivative 10. Carbon nucleophiles such as ethyl cyanoacetate and/or malononitrile were subjected to react with 4 to give oxopropanoate 11 and/or oxopropanoic acid 12 derivatives, respectively. Microwave irradiation of 4 and formamide yielded the pyrimidinone derivative 13, which were subjected to react with phosphorous pentasulfide, a mixture of phosphorous oxychloride and phosphorous pentachloride and/or methyl iodide, to give 14, 15, and/or 16, respectively.