2,5-bis(1,3-benzodithiol-2-yl)-1-methylpyrrole | 153850-73-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,5-bis(1,3-benzodithiol-2-yl)-1-methylpyrrole
• CAS: 153850-73-8
• 化学式: C₁₉H₁₅NS₄
• 分子量: 385.599
• InChiKey: YSKVBFSNUJVFHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-bis(1,3-benzodithiol-2-yl)-1-methylpyrrole 在 tetrafluoroboric acid 、 mercury(II) oxide 作用下， 以 二甲基亚砜 为溶剂， 以90%的产率得到1-methyl-1H-pyrrole-2,5-diformaldehyde
  参考文献：
  名称：

  A convenient general method for the synthesis of pyrrole-2,5-dicarbaldehydes

  摘要：

  A new general method for the synthesis of pyrrole-2,5-dicarbaldehyde and its 3-mono- and 3,4-disubstituted derivatives is reported. It involves the intermediate formation of the corresponding 2,5-bis(1,3-benzodithiol-2-yl)pyrroles followed by hydrolysis with HgO-35% aq. HBF4-DMSO. Pyrrole-2,5-dicarbaldehyde was obtained in overall yields of 43-65%, whilst that of the derivatives was 32-90%. Moreover the methylation of the corresponding dithiolic intermediate with further hydrolysis resulted in the formation of 1-methylpyrrole-2,5-dicarbaldehyde in 90% overall yield.

  DOI：

  10.1039/p19930002939
• 作为产物：
  描述：

  2-(3-methylbutoxy)-1,3-benzodithiole 在 sodium hydroxide 、 四乙基溴化铵 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2,5-bis(1,3-benzodithiol-2-yl)-1-methylpyrrole
  参考文献：
  名称：

  A convenient general method for the synthesis of pyrrole-2,5-dicarbaldehydes

  摘要：

  A new general method for the synthesis of pyrrole-2,5-dicarbaldehyde and its 3-mono- and 3,4-disubstituted derivatives is reported. It involves the intermediate formation of the corresponding 2,5-bis(1,3-benzodithiol-2-yl)pyrroles followed by hydrolysis with HgO-35% aq. HBF4-DMSO. Pyrrole-2,5-dicarbaldehyde was obtained in overall yields of 43-65%, whilst that of the derivatives was 32-90%. Moreover the methylation of the corresponding dithiolic intermediate with further hydrolysis resulted in the formation of 1-methylpyrrole-2,5-dicarbaldehyde in 90% overall yield.

  DOI：

  10.1039/p19930002939

文献信息

• A convenient general method for the synthesis of pyrrole-2,5-dicarbaldehydes
  作者：Silvano Cadamuro、Iacopo Degani、Rita Fochi、Antonella Gatti、Laura Piscopo

  DOI：10.1039/p19930002939

  日期：——

  A new general method for the synthesis of pyrrole-2,5-dicarbaldehyde and its 3-mono- and 3,4-disubstituted derivatives is reported. It involves the intermediate formation of the corresponding 2,5-bis(1,3-benzodithiol-2-yl)pyrroles followed by hydrolysis with HgO-35% aq. HBF4-DMSO. Pyrrole-2,5-dicarbaldehyde was obtained in overall yields of 43-65%, whilst that of the derivatives was 32-90%. Moreover the methylation of the corresponding dithiolic intermediate with further hydrolysis resulted in the formation of 1-methylpyrrole-2,5-dicarbaldehyde in 90% overall yield.