2-formyldipyrromethane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-formyldipyrromethane
• 英文别名: 5-(1H-pyrrol-2-ylmethyl)-1H-pyrrole-3-carbaldehyde
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: YSNHJLQQANLFMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.6
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吡咯-3-甲醛 以 乙腈 为溶剂， 反应 0.5h， 生成 2-formyldipyrromethane
  参考文献：
  名称：

  Mild Microwave-Assisted Synthesis of Dipyrromethanes and Their Analogues

  摘要：

  The Mannich reaction between pyrroles or indoles and Eschenmoser's salt (dimethylmethylideneammonium iodide) forms N,N-dimethylamino-methylated derivatives in good to excellent yields. The reaction is highly regioselective, and for pyrroles both 2- and 3-substituted derivatives could be obtained. The N,N-dimethylaminomethylpyrroles and indoles underwent substitution with pyrrole under microwave irradiation, affording the appropriate dipyrromethanes, N-confused, and indolo-dipyrromethanes in moderate to excellent overall yield.

  DOI：

  10.1055/s-0034-1378925

文献信息

• Direct Synthesis of Magnesium Porphine via 1-Formyldipyrromethane
  作者：Dilek Kiper Dogutan、Marcin Ptaszek、Jonathan S. Lindsey

  DOI：10.1021/jo070532z

  日期：2007.6.1

  The reaction of 1-formyldipyrromethane (100 mM) in toluene at 115 °C containing DBU (10 mol equiv) and MgBr2 (3 mol equiv) in the presence of air affords the magnesium chelate Mg(II) porphine in 30−40% yield. The advantages of the new method include simplicity, high concentration, chromatography-free purification, gram-scale synthesis, and avoidance of the poorly soluble free base porphine. Mg(II)

  含有DBU（10摩尔当量）和MgBr 2（3摩尔当量）的1-甲酰基二吡咯甲烷（100 mM）在甲苯中于115°C在空气中存在下反应，制得30-40％的螯合镁Mg（II）卟啉镁屈服。新方法的优点包括简单，高浓度，无色谱纯化，克级合成，以及避免了难溶的游离碱吗啡。Mg（II）卟啉在普通有机溶剂中表现出良好的溶解性，并且是衍生化的有价值的核心支架。
• Mild Microwave-Assisted Synthesis of Dipyrromethanes and Their Analogues
  作者：K. Borbas、Ruisheng Xiong

  DOI：10.1055/s-0034-1378925

  日期：——

  The Mannich reaction between pyrroles or indoles and Eschenmoser's salt (dimethylmethylideneammonium iodide) forms N,N-dimethylamino-methylated derivatives in good to excellent yields. The reaction is highly regioselective, and for pyrroles both 2- and 3-substituted derivatives could be obtained. The N,N-dimethylaminomethylpyrroles and indoles underwent substitution with pyrrole under microwave irradiation, affording the appropriate dipyrromethanes, N-confused, and indolo-dipyrromethanes in moderate to excellent overall yield.