5-(5,5-dimethyl-1,3-dioxan-2-yl)-1-formyldipyrromethane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(5,5-dimethyl-1,3-dioxan-2-yl)-1-formyldipyrromethane
• 英文别名: 5-[(5,5-dimethyl-1,3-dioxan-2-yl)-(1H-pyrrol-2-yl)methyl]-1H-pyrrole-2-carbaldehyde
• 化学式: C₁₆H₂₀N₂O₃
• 分子量: 288.346
• InChiKey: SOEQWXTVZICFST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  67.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲酸苯酯 、 5-(5,5-dimethyl-1,3-dioxan-2-yl)dipyrromethane 在 magnesium,1,3,5-trimethylbenzene-6-ide,bromide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 3.17h， 以65%的产率得到5-(5,5-dimethyl-1,3-dioxan-2-yl)-1-formyldipyrromethane
  参考文献：
  名称：

  Synthesis of 1-Formyldipyrromethanes

  摘要：

  1-Formyldipyrromethanes are versatile precursors to porphyrins and chlorins. Two methods of synthesis of 1-formyl-dipyrromethanes have been investigated: (1) Vilsmeier formylation followed by selective removal of the unwanted 1,9-diformyldipyrromethane by dialkyltin complexation and (2) reaction with mesitylmagnesium bromide (MesMgBr) followed by formylation with phenyl formate. The two approaches are complementary (acidic versus basic conditions; statistical versus selective formylation). The latter was found to be more efficient for the preparation of 1-formyl-dipyrromethanes.

  DOI：

  10.1021/jo060119b

文献信息

• Synthesis of 1-Formyldipyrromethanes
  作者：Marcin Ptaszek、Brian E. McDowell、Jonathan S. Lindsey

  DOI：10.1021/jo060119b

  日期：2006.5.1

  1-Formyldipyrromethanes are versatile precursors to porphyrins and chlorins. Two methods of synthesis of 1-formyl-dipyrromethanes have been investigated: (1) Vilsmeier formylation followed by selective removal of the unwanted 1,9-diformyldipyrromethane by dialkyltin complexation and (2) reaction with mesitylmagnesium bromide (MesMgBr) followed by formylation with phenyl formate. The two approaches are complementary (acidic versus basic conditions; statistical versus selective formylation). The latter was found to be more efficient for the preparation of 1-formyl-dipyrromethanes.