ethyl 5-methyl-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-methyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate
• 英文别名: ethyl 5-methyl-4-(1,2,3-thiadiazol-4-yl)-2-furoate；5-methyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylic acid ethyl ester；Ethyl 4-(1,2,3-thiadiazol-4-yl)-5-methylfuran-2-carboxylate；ethyl 5-methyl-4-(thiadiazol-4-yl)furan-2-carboxylate
• 化学式: C₁₀H₁₀N₂O₃S
• 分子量: 238.267
• InChiKey: VWKRORXYHYPJMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 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-methyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 1.5h， 以78%的产率得到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
• 作为产物：
  描述：

  5-methyl-furan-2-carboxylic acid ethyl ester 在 氯化亚砜 、 四氯化锡 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 3.5h， 生成 ethyl 5-methyl-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

• Reactions of Ethyl 5-Methyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate with Selected Bases
  作者：Yu. O. Remizov、L. M. Pevzner、M. L. Petrov

  DOI：10.1134/s1070363219100256

  日期：2019.10

  reactions of 5-methyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylic acid ethyl ester with some bases have been studied. The opening of 1,2,3-thiadiazole ring under the action of potassium tert-butylate in tetrahydrofuran in the presence of methyl iodide has led to the corresponding 4-methylsulfanylethynylfuran derivative. Under the action of potassium carbonate in DMF with an excess of primary amines or morpholine

  研究了5-甲基-4-（1,2,3-噻二唑-4-基）呋喃-2-甲酸乙酯与某些碱的反应。在存在碘甲烷的情况下，在四氢呋喃中叔丁醇钾盐的作用下，1,2,3-噻二唑环的打开导致产生了相应的4-甲基磺酰间乙炔基呋喃衍生物。在DMF中碳酸钾与过量的伯胺或吗啉的作用下，起始噻二唑形成了相应的呋喃乙酸硫代酰胺。5-甲基-4-（1,2,3-噻二唑-4-基）呋喃-2-甲酸乙酯与水合肼的反应导致酯基发生肼解反应而未裂解1,2,3-噻二唑环。
• 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
• 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: 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