(Z)-ethyl [2,5-dihydro-3-(4-toluenesulfonyloxy)-5-oxo-2-thienylidene]acetate | 210891-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-ethyl [2,5-dihydro-3-(4-toluenesulfonyloxy)-5-oxo-2-thienylidene]acetate
• 英文别名: ethyl (2Z)-2-[3-(4-methylphenyl)sulfonyloxy-5-oxothiophen-2-ylidene]acetate
• CAS: 210891-61-5
• 化学式: C₁₅H₁₄O₆S₂
• 分子量: 354.405
• InChiKey: ZEUAOCLHNJCXFH-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl [2,5-dihydro-3-(4-toluenesulfonyloxy)-5-oxo-2-thienylidene]acetate 在 4-二甲氨基吡啶 、 sodium azide 、 1-环已基-2-吗啉乙基碳二亚胺对甲苯磺酸盐 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 20.0h， 生成 (5Z)-4-amino-5-[2-(3,5-dimethylpyrazol-1-yl)-2-oxoethylidene]thiophen-2-one
  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：

  (Z)-ethyl (5-ethoxy-4-ethoxycarbonyl-2,3-dihydro-3-oxo-2-thienylidene)acetate 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.75h， 生成 (Z)-ethyl [2,5-dihydro-3-(4-toluenesulfonyloxy)-5-oxo-2-thienylidene]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

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.