2,5-bis(1,3-benzodithiol-2-yl)-3-formylpyrrole | 153850-69-2

• 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)-3-formylpyrrole
• 英文别名: 2,5-bis(1,3-benzodithiol-2-yl)-1H-pyrrole-3-carbaldehyde
• CAS: 153850-69-2
• 化学式: C₁₉H₁₃NOS₄
• 分子量: 399.582
• InChiKey: AAFZMYRURFKHSW-UHFFFAOYSA-N

物化性质

• 沸点：
  620.4±55.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-bis(1,3-benzodithiol-2-yl)-3-formylpyrrole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以77%的产率得到2,5-Bis-benzo[1,3]dithiol-2-yl-3-methyl-1H-pyrrole
  参考文献：
  名称：

  Convenient route for the synthesis of 3-substituted and 3,4-disubstituted pyrrole-2,5-dicarbaldehydes

  摘要：

  通过用 HgO–35% 水溶液水解得到 3-取代和 3,4-二取代吡咯-2,5-二甲醛。通过 2,5-双(1,3-苯并二硫醇-2-基)吡咯的亲电取代反应制备中间体 4 和 5 的 HBF4-DMSO。从吡咯开始的总产率为 41-88%。

  DOI：

  10.1039/p19960002365
• 作为产物：
  描述：

  2-(3-methylbutoxy)-1,3-benzodithiole 、 吡咯-3-甲醛 在 溶剂黄146 作用下， 反应 2.0h， 以90%的产率得到2,5-bis(1,3-benzodithiol-2-yl)-3-formylpyrrole
  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.
• Convenient route for the synthesis of 3-substituted and 3,4-disubstituted pyrrole-2,5-dicarbaldehydes
  作者：Silvano Cadamuro、Iacopo Degani、Rita Fochi、Antonella Gatti、Laura Piscopo

  DOI：10.1039/p19960002365

  日期：——

  3-Substituted and 3,4-disubstituted pyrrole-2,5-dicarbaldehydes have been obtained by hydrolysis with HgO–35% aq. HBF4–DMSO of the intermediates 4 and 5 prepared by electrophilic substitution reactions on 2,5-bis(1,3-benzodithiol-2-yl)pyrrole. The overall yields starting from pyrrole ranged from 41–88%.

  通过用 HgO–35% 水溶液水解得到 3-取代和 3,4-二取代吡咯-2,5-二甲醛。通过 2,5-双(1,3-苯并二硫醇-2-基)吡咯的亲电取代反应制备中间体 4 和 5 的 HBF4-DMSO。从吡咯开始的总产率为 41-88%。