ethyl (5Z)-5-[(2E)-2-(dimethylhydrazinylidene)ethylidene]-4-methoxy-2-oxothiophene-3-carboxylate | 210891-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: ethyl (5Z)-5-[(2E)-2-(dimethylhydrazinylidene)ethylidene]-4-methoxy-2-oxothiophene-3-carboxylate
• CAS: 210891-44-4
• 化学式: C₁₂H₁₆N₂O₄S
• 分子量: 284.336
• InChiKey: CABXLSSAJGJXGV-WNDPTYLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  93.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (5Z)-5-[(2E)-2-(dimethylhydrazinylidene)ethylidene]-4-methoxy-2-oxothiophene-3-carboxylate 在 氨 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以97%的产率得到ethyl (5Z)-4-amino-5-[(2E)-2-(dimethylhydrazinylidene)ethylidene]-2-oxothiophene-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological activity of thiobasidalin

  摘要：

  Thiobasidalin 2, the thiolactone analogue of the antibiotic basidalin 1, is synthesized starting from easily accessible thiotetronic acid 3 via a straightforward reaction sequence employing the chemoselective lithium aluminum hydride reduction of the acid pyrazolide 31 as the final key step. Antimicrobial tests reveal that thiobasidalin 2 as well as a number of its synthetic congeners display considerable activity against both eucaryontes and procaryontes. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80064-0
• 作为产物：
  描述：

  ethyl 3-hydroxy-5-oxo-2H-thiophene-4-carboxylate 在 哌啶 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 6.0h， 生成 ethyl (5Z)-5-[(2E)-2-(dimethylhydrazinylidene)ethylidene]-4-methoxy-2-oxothiophene-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological activity of thiobasidalin

  摘要：

  Thiobasidalin 2, the thiolactone analogue of the antibiotic basidalin 1, is synthesized starting from easily accessible thiotetronic acid 3 via a straightforward reaction sequence employing the chemoselective lithium aluminum hydride reduction of the acid pyrazolide 31 as the final key step. Antimicrobial tests reveal that thiobasidalin 2 as well as a number of its synthetic congeners display considerable activity against both eucaryontes and procaryontes. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80064-0

文献信息

• Synthesis and biological activity of thiobasidalin
  作者：Josef E. Schachtner、Hans-Dietrich Stachel、Kurt Polborn、Timm Anke

  DOI：10.1016/s0223-5234(98)80064-0

  日期：1998.4

  Thiobasidalin 2, the thiolactone analogue of the antibiotic basidalin 1, is synthesized starting from easily accessible thiotetronic acid 3 via a straightforward reaction sequence employing the chemoselective lithium aluminum hydride reduction of the acid pyrazolide 31 as the final key step. Antimicrobial tests reveal that thiobasidalin 2 as well as a number of its synthetic congeners display considerable activity against both eucaryontes and procaryontes. (C) Elsevier, Paris.