ethyl 5-(bromomethyl)-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 5-(bromomethyl)-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate
• 英文别名: Ethyl 4-(1,2,3-thiadiazol-4-yl)-5-(bromomethyl)furan-2-carboxylate；ethyl 5-(bromomethyl)-4-(thiadiazol-4-yl)furan-2-carboxylate
• 化学式: C₁₀H₉BrN₂O₃S
• 分子量: 317.163
• InChiKey: BUOUXYUHEXKVRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  93.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-(bromomethyl)-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate 在 水 、 sodium acetate 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 5-hydroxymethyl-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
• 作为产物：
  描述：

  5-methyl-furan-2-carboxylic acid ethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 偶氮二异丁腈 、 四氯化锡 、 溶剂黄146 作用下， 以 四氯化碳 、 乙醇 、 氯仿 为溶剂， 反应 5.0h， 生成 ethyl 5-(bromomethyl)-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate
  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

• 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
• In Vitro Activity of Organochalcogen Compounds: IV. Synthesis and Cytotoxic Effect of 4-(1,2,3-Thiadiazol-4-yl)furans Against HeLa, Sk-mel-2, and B16 Tumor Cell Lines
  作者：L. M. Pevzner、E. A. Makhneva、S. V. Shmakov、M. L. Petrov、A. V. Stepakov、V. M. Boitsov

  DOI：10.1134/s1070363223060245

  日期：2023.6