4H-thieno[3,2-b]pyrrol-6-ol | 1157936-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 英文名称: 4H-thieno[3,2-b]pyrrol-6-ol
• CAS: 1157936-32-7
• 化学式: C₆H₅NOS
• 分子量: 139.178
• InChiKey: QLLKCDIFJZHKEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-methylthieno<3,2-c>isoxazole 以95%的产率得到4H-thieno[3,2-b]pyrrol-6-ol
  参考文献：
  名称：

  Flash vacuum pyrolysis of 2-acetyl-3-azido[1]benzothiophene

  摘要：

  Flash vacuum pyrolysis (FVP) of 2-acetyl-3-azido[1]benzothiophene at 300 degrees C provides 3-methyl[1]benzothieno[3,2-c]isoxazole (72%). At higher temperatures, the heteroindoxyl 1,2-dihydro[1]benzothieno[3,2-b]pyrrol-3-one was obtained in low yield (ca. 10%). The heteroindoxyl exists as a mixture of keto and enol forms in DMSO solution. Because of the easy oxidative dimerisation of these products to indigotin (and its heteroanalogues), such reactions are excellent examples of the synthetic advantages of FVP with the monomeric products conveniently generated under vacuum in a solvent-free, air-free environment.[GRAPHICS].

  DOI：

  10.24820/ark.5550190.p011.239

文献信息

• Flash vacuum pyrolysis of 2-acetyl-3-azido[1]benzothiophene
  作者：Alexander P. Gaywood、Hamish McNab、Lilian McNab

  DOI：10.24820/ark.5550190.p011.239

  日期：——

  Flash vacuum pyrolysis (FVP) of 2-acetyl-3-azido[1]benzothiophene at 300 degrees C provides 3-methyl[1]benzothieno[3,2-c]isoxazole (72%). At higher temperatures, the heteroindoxyl 1,2-dihydro[1]benzothieno[3,2-b]pyrrol-3-one was obtained in low yield (ca. 10%). The heteroindoxyl exists as a mixture of keto and enol forms in DMSO solution. Because of the easy oxidative dimerisation of these products to indigotin (and its heteroanalogues), such reactions are excellent examples of the synthetic advantages of FVP with the monomeric products conveniently generated under vacuum in a solvent-free, air-free environment.[GRAPHICS].