1-chloro-3-(methoxycarbonyl)isothianaphthene | 136132-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1-chloro-3-(methoxycarbonyl)isothianaphthene
• 英文别名: Methyl 3-chloro-2-benzothiophene-1-carboxylate
• CAS: 136132-55-3
• 化学式: C₁₀H₇ClO₂S
• 分子量: 226.683
• InChiKey: VOGODTFEWJGDHC-UHFFFAOYSA-N

物化性质

• 沸点：
  351.0±22.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-二氢-2-苯并噻吩-1,3-二酮 在 正丁基锂 、 五氯化磷 、 sodium iodide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 1-chloro-3-(methoxycarbonyl)isothianaphthene
  参考文献：
  名称：

  A new route to 1,3-disubstituted benzo[c]thiophenes

  摘要：

  A facile synthesis of 1,3-dichlorobenzo[c]thiophene 3 is described. Lithium-chlorine exchange of 3, followed by reaction with various electrophiles, provides a route to 1-acyl-3-chlorobenzo[c]thiophenes, as well as to the very stable 1,3-bis(tert-butyldimethylsilyl)benzo[c]thiophene (9). Compound 9 undergoes silyl replacement reactions with acylating agents, as well as an unusual oxidative desilylation by I2 or TiCl4, to give the capped disilylated dimer, trimer, and tetramer (16, 17, and 18) of benzo[c]thiophene.

  DOI：

  10.1021/jo00021a012

文献信息

• A new route to 1,3-disubstituted benzo[c]thiophenes
  作者：Yoshihiro Okuda、M. V. Lakshmikantham、Michael P. Cava

  DOI：10.1021/jo00021a012

  日期：1991.10

  A facile synthesis of 1,3-dichlorobenzo[c]thiophene 3 is described. Lithium-chlorine exchange of 3, followed by reaction with various electrophiles, provides a route to 1-acyl-3-chlorobenzo[c]thiophenes, as well as to the very stable 1,3-bis(tert-butyldimethylsilyl)benzo[c]thiophene (9). Compound 9 undergoes silyl replacement reactions with acylating agents, as well as an unusual oxidative desilylation by I2 or TiCl4, to give the capped disilylated dimer, trimer, and tetramer (16, 17, and 18) of benzo[c]thiophene.