2-Ethoxy-4-oxo-4,5-dihydro-thiophene-3-carboxylic acid ethyl ester | 210891-58-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 2-Ethoxy-4-oxo-4,5-dihydro-thiophene-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-ethoxy-4-oxothiophene-3-carboxylate
• CAS: 210891-58-0
• 化学式: C₉H₁₂O₄S
• 分子量: 216.258
• InChiKey: PBDMHQADSFWAJM-UHFFFAOYSA-N

物化性质

• 沸点：
  349.8±42.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Ethoxy-4-oxo-4,5-dihydro-thiophene-3-carboxylic acid ethyl ester 在 copper(I) chloride 、 盐酸 、 sodium tetrahydroborate 、 sodium azide 、 三乙胺 、 tin(ll) chloride 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 5.0h， 生成 ethyl (3-amino-2,5-dihydro-5-oxo-2-thienyl)acetate
  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 、 triethyloxonium fluoroborate 以 二氯甲烷 为溶剂， 反应 50.0h， 以30%的产率得到2-Ethoxy-4-oxo-4,5-dihydro-thiophene-3-carboxylic acid ethyl ester
  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.