ethyl 2-bromomethyl-5-(1,2,3-thiadiazol-4-yl)-furan-3-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 2-bromomethyl-5-(1,2,3-thiadiazol-4-yl)-furan-3-carboxylate
• 英文别名: ethyl 2-bromomethyl-5-(1,2,3-thiadiazol-4-yl)-3-furoate；Ethyl 2-bromomethyl-5-(1,2,3-thiadiazol-4-yl)furan-3-carboxylate；ethyl 2-(bromomethyl)-5-(thiadiazol-4-yl)furan-3-carboxylate
• 化学式: C₁₀H₉BrN₂O₃S
• 分子量: 317.163
• InChiKey: SEVMAEWFWFHGLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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 2-bromomethyl-5-(1,2,3-thiadiazol-4-yl)-furan-3-carboxylate 在 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 14.5h， 生成 Ethyl 2-[[[2-(4-methylpiperidin-1-yl)acetyl]amino]methyl]-5-(thiadiazol-4-yl)furan-3-carboxylate
  参考文献：
  名称：

  Synthesis of alkyl 2-aminomethyl-5-(1,2,3-thiadiazol-4-yl)furan-3-carboxylate and pseudopeptides on its basis

  摘要：

  Cyclization of alkyl 2-methyl-5-acetylfuran-3-carboxylate carbethoxyhydrazone according to Hurd-Mori reaction afforded alkyl 2-methyl-5-(1,2,3-thiadiazol-4-yl)-3-carboxylate. Its bromination with N-bromosuccinimide yielded 2-bromomethyl derivative. The latter was involved in the Delepine reaction to form alkyl 2-aminomethyl-5-(1,2,3-thiadiazol-4-yl)-3-carboxylate. Acylation of the product synthesized with chloroacetyl chloride and subsequent treatment with morpholine or 4-methylpiperidine gave the corresponding pseudopeptides. In the course of these transformations the furylthiadiazole fragment retained its stability.

  DOI：

  10.1134/s1070363215040179
• 作为产物：
  描述：

  5-乙酰基-2-甲基-3-呋喃乙酯 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 偶氮二异丁腈 、 溶剂黄146 作用下， 以 四氯化碳 、 氯仿 、 异丙醇 为溶剂， 反应 19.5h， 生成 ethyl 2-bromomethyl-5-(1,2,3-thiadiazol-4-yl)-furan-3-carboxylate
  参考文献：
  名称：

  Synthesis of alkyl 2-aminomethyl-5-(1,2,3-thiadiazol-4-yl)furan-3-carboxylate and pseudopeptides on its basis

  摘要：

  Cyclization of alkyl 2-methyl-5-acetylfuran-3-carboxylate carbethoxyhydrazone according to Hurd-Mori reaction afforded alkyl 2-methyl-5-(1,2,3-thiadiazol-4-yl)-3-carboxylate. Its bromination with N-bromosuccinimide yielded 2-bromomethyl derivative. The latter was involved in the Delepine reaction to form alkyl 2-aminomethyl-5-(1,2,3-thiadiazol-4-yl)-3-carboxylate. Acylation of the product synthesized with chloroacetyl chloride and subsequent treatment with morpholine or 4-methylpiperidine gave the corresponding pseudopeptides. In the course of these transformations the furylthiadiazole fragment retained its stability.

  DOI：

  10.1134/s1070363215040179

文献信息

• Ethyl 2-bromomethyl-5-(1,2,3-thiadiazol-4-yl)furan-3-carboxylate in reactions with O-, S-, N-, and P-nucleophiles
  作者：R. Maadadi、L. M. Pevzner、M. L. Petrov

  DOI：10.1134/s1070363216110104

  日期：2016.11

  exclusively. Reaction with excess 2-aminoethanol permits to prepare secondary amine, and the reactions with pyrrolidine, piperidine, and morpholine give the corresponding tertiary amines. Phosphorylation with triethyl phosphite under the conditions of Arbuzov reaction leads to the corresponding diethyl phosphonate. In all these transformations furylthiadiazole fragment is retained.

  研究了2-溴甲基-5-（1,2,3-噻二唑-4-基）呋喃-3-甲酸乙酯与不同性质的亲核试剂的反应。结果表明，在乙酸中乙酸钠的作用下，溴被乙酰氧基取代。较强的碱（如酚盐）会引起不稳定的呋喃噻二唑片段的大量分解，只有在相转移催化剂存在下，在离子对萃取条件下进行该反应时，才能避免分解。在与N，N-二乙基二硫代氨基甲酸钠反应中，形成相应的硫酯。丁硫醇和硫酚被烷基化为硫醇钾。在最后一种情况下，S-烷基化仅进行。与过量的2-氨基乙醇反应可以制备仲胺，与吡咯烷，哌啶和吗啉的反应可得到相应的叔胺。在Arbuzov反应的条件下用亚磷酸三乙酯进行磷酸化反应得到相应的膦酸二乙酯。在所有这些转化中，保留了呋喃噻二唑片段。