2,5-Bis(1,3-benzodithiol-2-yl)pyrrole | 58488-39-4

• 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)pyrrole
• 英文别名: 2,5-bis(1,3-benzodithiol-2-yl)-1H-pyrrole
• CAS: 58488-39-4
• 化学式: C₁₈H₁₃NS₄
• 分子量: 371.572
• InChiKey: FLKGKAJKCGEVNL-UHFFFAOYSA-N

物化性质

• 熔点：
  163-164 °C
• 沸点：
  591.0±50.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-Bis(1,3-benzodithiol-2-yl)pyrrole 在 tetrafluoroboric acid 、 mercury(II) oxide 作用下， 以 二甲基亚砜 为溶剂， 以50%的产率得到1H-吡咯-2,5-二甲醛
  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 、 吡咯 以 溶剂黄146 为溶剂， 生成 2,5-Bis(1,3-benzodithiol-2-yl)pyrrole
  参考文献：
  名称：

  2-(3-甲基丁氧基)-1,3-苯并二噻吩：一种将环状二硫缩醛功能引入吲哚和吡咯的 2 位或 3 位的便捷试剂

  摘要：

  一种新试剂 2-(3-甲基丁氧基)-1,3-苯并二硫醇可用于在温和条件下以几乎定量的产率将环状二硫缩醛官能团引入吲哚和吡咯的 2-或 3-位。

  DOI：

  10.1246/cl.1975.1319

文献信息

• Heterofulvalenes. I. 5-Aza- and 6-Aza-1,4-dithiafulvalenes
  作者：Jyuzo Nakayama、Yukie Watabe、Masamatsu Hoshino

  DOI：10.1246/bcsj.51.1427

  日期：1978.5

  5-Aza, 2,3-benzo-5-aza-, 6-aza-, and 2,3-benzo-6-aza-1,4-dithiafulvalenes were synthesized and their spectroscopic properties are described. For example, the reaction of 2-methylthio-1,3-dithiolylium iodide with pyrrole gave 2-(2-pyrrolyl)-1,3-dithiolylium iodide in a 92% yield, which was treated with DBU, giving rise to 5-aza-1,4-dithiafulvalene as thermally-stable orange crystals in an 82% yield. Several reactions found during the course of these synthetic studies are also reported.

  合成了5-阿扎、2,3-苯并-5-阿扎、6-阿扎以及2,3-苯并-6-阿扎-1,4-二硫二氟烯，并描述了它们的光谱性质。例如，2-甲硫基-1,3-二硫基喹啉碘化物与吡咯的反应生成了2-(2-吡咯基)-1,3-二硫基喹啉碘化物，收率为92%；该产物与DBU反应，生成了热稳定的橙色晶体5-阿扎-1,4-二硫二氟烯，收率为82%。在这些合成研究过程中发现的几种反应也被报告。
• 2-(3-METHYLBUTOXY)-1,3-BENZODITHIOLE: A CONVENIENT REAGENT FOR INTRODUCTION OF A CYCLIC DITHIOACETAL FUNCTION INTO 2- OR 3-POSITION OF INDOLES AND PYRROLES
  作者：Jyuzo Nakayama、Mimiko Imura、Masamatsu Hoshino

  DOI：10.1246/cl.1975.1319

  日期：1975.12.5

  A new reagent, 2-(3-methylbutoxy)-1,3-benzodithiole, could be used to introduce a cyclic dithioacetal function into 2- or 3-position of indoles and pyrroles in almost quantitative yields under mild conditions.

  一种新试剂 2-(3-甲基丁氧基)-1,3-苯并二硫醇可用于在温和条件下以几乎定量的产率将环状二硫缩醛官能团引入吲哚和吡咯的 2-或 3-位。
• 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%。
• NAKAYAMA J.; IMURA M.; HOSHINO M., CHEM. LETT, 1975, NO 12, 1319-1320
  作者：NAKAYAMA J.、 IMURA M.、 HOSHINO M.

  DOI：——

  日期：——
• 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.