ethyl-[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-amine | 35313-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl-[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-amine
• 英文别名: N-Ethyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine
• CAS: 35313-95-2
• 化学式: C₁₃H₁₇N₃O₃S
• 分子量: 295.362
• InChiKey: OHISBGLPBCUMAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  219-220 °C(Solv: ethanol (64-17-5))
• 沸点：
  436.5±55.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰肼 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 ethyl-[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-amine
  参考文献：
  名称：

  1,3,4-THIADIAZOLES. REGIOSELECTIVE O-DEMETHYLATION ON DEHYDRATIVE CYCLIZATION OF 1-(3,4,5-TRIMETHOXYBENZOYL)4-SUBSTITUTED THIOSEMICARBAZIDES WITH SULPHURIC ACID

  摘要：

  Cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-substituted thiosemicarbazides 2a-g with sulphuric acid at ambient temperature afforded the selectively demethylated products 2-(4-hydroxy-3,5-dimethoxyphenyl)5-substituted amino-1,3,4-thiodiazoles 4a-g. Meanwhile, dehydrative cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-(benzyl or t-butyl)thiosemicarbazides 2h,i with sulphuric acid yielded 2-(4-hydroxy-3,5-dimethoxyphenyl)-5-amino-1,3,4-thiadiazole 5. On the other hand, dehydration of 2h,i by heating with phosphorus oxychloride yielded 2-(3,4,5-trimethoxyphenyl)-5-amino-1,3,4-thiadiazole 6.

  DOI：

  10.1080/10426500490485525

文献信息

• Mazzone; Bonina; Puglisi, Farmaco, Edizione Scientifica, 1982, vol. 37, # 10, p. 685 - 700
  作者：Mazzone、Bonina、Puglisi、Arrigo、Cosentino、Blandino

  DOI：——

  日期：——
• Synthesis and hypoglycemic activity of 3-aryl(or pyridyl)-5-alkyl(or aryl)amino-1,3,4-thiadiazoles and some sulfonylurea derivatives of 4H-1,2,4-triazoles
  作者：C. V. Deliwala、M. Y. Mhasalkar、M. H. Shah、P. D. Pilankar、S. T. Nikam、K. G. Anantanarayanan

  DOI：10.1021/jm00292a035

  日期：1971.10
• MAZZONE, G.;BONINA, F.;PUGLISI, G.;ARRIGO, REINA, R.;COSENTINO, C.;BLANDI+, FARMACO ED. SCI., 1982, 37, N 10, 685-700
  作者：MAZZONE, G.、BONINA, F.、PUGLISI, G.、ARRIGO, REINA, R.、COSENTINO, C.、BLANDI+

  DOI：——

  日期：——
• 1,3,4-THIADIAZOLES. REGIOSELECTIVE <i>O</i>-DEMETHYLATION ON DEHYDRATIVE CYCLIZATION OF 1-(3,4,5-TRIMETHOXYBENZOYL)4-SUBSTITUTED THIOSEMICARBAZIDES WITH SULPHURIC ACID
  作者：Mohamed Al-Omar、Omar A. Al-Deeb、Hamad A. Al-Khamees、Ali A. El-Emam

  DOI：10.1080/10426500490485525

  日期：2004.12.1

  Cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-substituted thiosemicarbazides 2a-g with sulphuric acid at ambient temperature afforded the selectively demethylated products 2-(4-hydroxy-3,5-dimethoxyphenyl)5-substituted amino-1,3,4-thiodiazoles 4a-g. Meanwhile, dehydrative cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-(benzyl or t-butyl)thiosemicarbazides 2h,i with sulphuric acid yielded 2-(4-hydroxy-3,5-dimethoxyphenyl)-5-amino-1,3,4-thiadiazole 5. On the other hand, dehydration of 2h,i by heating with phosphorus oxychloride yielded 2-(3,4,5-trimethoxyphenyl)-5-amino-1,3,4-thiadiazole 6.