4,5-Dibromo-1-ethylpyrrole-2-carbaldehyde | 877238-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-Dibromo-1-ethylpyrrole-2-carbaldehyde
• CAS: 877238-85-2
• 化学式: C₇H₇Br₂NO
• 分子量: 280.947
• InChiKey: RWMSGUKQTORXLS-UHFFFAOYSA-N

物化性质

• 熔点：
  71-73 °C
• 沸点：
  325.5±37.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,5-Dibromo-1-ethylpyrrole-2-carbaldehyde 、 4-氟苯硼酸 、 4-甲氧基苯硼酸 在 palladium diacetate 、 potassium carbonate 、 sodium carbonate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 3.0h， 以51%的产率得到1-ethyl-5-(4'-fluorophenyl)-4-(4'-methoxyphenyl)pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Regioselective Dicouplings:  Application to Differentially Substituted Pyrroles

  摘要：

  In an effort to develop a more concise route to differentially substituted pyrroles (such as that found in the lamellarins), a completely regioselective one-pot double Suzuki coupling has been discovered. The key feature is the use of a ligand-free palladium catalyst under optimized conditions, which results only in coupling of the C5 bromide. At this point, addition of a second boronic acid and a phosphine ligand enables coupling at the remaining C4 bromide.

  DOI：

  10.1021/ol0530981
• 作为产物：
  描述：

  2-吡咯甲醛 在 溴 、 碘 、 potassium carbonate 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 生成 4,5-Dibromo-1-ethylpyrrole-2-carbaldehyde
  参考文献：
  名称：

  Regioselective Dicouplings:  Application to Differentially Substituted Pyrroles

  摘要：

  In an effort to develop a more concise route to differentially substituted pyrroles (such as that found in the lamellarins), a completely regioselective one-pot double Suzuki coupling has been discovered. The key feature is the use of a ligand-free palladium catalyst under optimized conditions, which results only in coupling of the C5 bromide. At this point, addition of a second boronic acid and a phosphine ligand enables coupling at the remaining C4 bromide.

  DOI：

  10.1021/ol0530981

文献信息

• Regioselective Dicouplings:  Application to Differentially Substituted Pyrroles
  作者：Scott T. Handy、Jesse J. Sabatini

  DOI：10.1021/ol0530981

  日期：2006.4.1

  In an effort to develop a more concise route to differentially substituted pyrroles (such as that found in the lamellarins), a completely regioselective one-pot double Suzuki coupling has been discovered. The key feature is the use of a ligand-free palladium catalyst under optimized conditions, which results only in coupling of the C5 bromide. At this point, addition of a second boronic acid and a phosphine ligand enables coupling at the remaining C4 bromide.