5-methyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-methyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylic acid
• 英文别名: 5-Methyl-4-(1,2,3thiadiazol-4-yl)-2-furoic acid；5-methyl-4-(thiadiazol-4-yl)furan-2-carboxylic acid
• 化学式: C₈H₆N₂O₃S
• 分子量: 210.213
• InChiKey: IAWKLXMDNNWTPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-methyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylic acid 在 氨 作用下， 以 甲醇 为溶剂， 生成 5-methyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxamide
  参考文献：
  名称：

  In Vitro Activity of Organochalcogen Compounds: I. Cytotoxic Effect of 4-(1,2,3-Thiadiazol-4-yl)furans Against K562 and HeLa Tumor Cell Lines

  摘要：

  DOI：

  10.1134/s1070363220110328
• 作为产物：
  描述：

  5-methyl-furan-2-carboxylic acid ethyl ester 在 氯化亚砜 、 水 、 四氯化锡 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 7.0h， 生成 5-methyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of ethyl 4-(1,2,3-thiadiazol-4-yl)-5-(bromomethyl)furan-2-carboxylate and its reactions with nucleophiles

  摘要：

  By cyclization of carboethoxyhydrazone of ethyl 4-acetyl-5-methylfuran-2-carboxylate under the conditions of Hurd-Mori reaction ethyl 4-(1,2,3-thiadiazol-4-yl)-5-methylfuran-2-carboxylate was synthesized. The ester obtained was brominated with N-bromosuccinimide at the methyl group in the furan ring. This bromide reacts with various N-, S-, O-, and P-nucleophiles to form the corresponding substitution products. Furylthiadiazole fragment remains stable in the course of these transformations.

  DOI：

  10.1134/s1070363215120117

文献信息

• Synthesis of ethyl 4-(1,2,3-thiadiazol-4-yl)-5-(bromomethyl)furan-2-carboxylate and its reactions with nucleophiles
  作者：Yu. O. Remizov、L. M. Pevzner、M. L. Petrov、A. I. Ponyaev

  DOI：10.1134/s1070363215120117

  日期：2015.12

  By cyclization of carboethoxyhydrazone of ethyl 4-acetyl-5-methylfuran-2-carboxylate under the conditions of Hurd-Mori reaction ethyl 4-(1,2,3-thiadiazol-4-yl)-5-methylfuran-2-carboxylate was synthesized. The ester obtained was brominated with N-bromosuccinimide at the methyl group in the furan ring. This bromide reacts with various N-, S-, O-, and P-nucleophiles to form the corresponding substitution products. Furylthiadiazole fragment remains stable in the course of these transformations.
• In Vitro Activity of Organochalcogen Compounds: I. Cytotoxic Effect of 4-(1,2,3-Thiadiazol-4-yl)furans Against K562 and HeLa Tumor Cell Lines
  作者：Yu. O. Remizov、A. A Kornev、L. M. Pevzner、M. L. Petrov、V. M. Boitsov、A. V. Stepakov

  DOI：10.1134/s1070363220110328

  日期：2020.11