2-phenyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]thiazin-4-one | 63274-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]thiazin-4-one
• 英文别名: 2-phenyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d][1,3]thiazin-4-one；2-Phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d][1,3]thiazin-4-one
• CAS: 63274-59-9
• 化学式: C₁₆H₁₃NOS₂
• 分子量: 299.417
• InChiKey: MCWAEDZHKWVZDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]thiazin-4-one 、 苄胺 反应 0.1h， 以10%的产率得到2-phenyl-4-benzyloxy-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidine
  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
• 作为产物：
  描述：

  2-phenyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d][1,3]thiazine-4-thione 在 氧气 作用下， 以 苯 为溶剂， 反应 3.0h， 以97%的产率得到2-phenyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]thiazin-4-one
  参考文献：
  名称：

  Wamhoff, Heinrich; Ertas, Muemtaz, Angewandte Chemie, 1982, vol. 94, # 10, p. 800 - 801

  摘要：

  DOI：

文献信息

• Leistner,S.; Wagner,G., Zeitschrift fur Chemie, 1977, vol. 17, p. 95 - 96
  作者：Leistner,S.、Wagner,G.

  DOI：——

  日期：——
• WAMHOFF, H.;ERTAS, M., ANGEW. CHEM., 1982, 94, N 10, 800-801
  作者：WAMHOFF, H.、ERTAS, M.

  DOI：——

  日期：——
• LEISTNER S.; WAGNER G., Z. CHEM. <ZECE-AL>, 1977, 17, NO 3, 95-96
  作者：LEISTNER S.、 WAGNER G.

  DOI：——

  日期：——
• 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.
• Wamhoff, Heinrich; Ertas, Muemtaz, Angewandte Chemie, 1982, vol. 94, # 10, p. 800 - 801
  作者：Wamhoff, Heinrich、Ertas, Muemtaz

  DOI：——

  日期：——