5-[1,5-bis(tert-butyldimethylsilyloxy)pent-3-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-[1,5-bis(tert-butyldimethylsilyloxy)pent-3-yl]-1-formyldipyrromethane
• 英文别名: 5-[4-[tert-butyl(dimethyl)silyl]oxy-2-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-1-(1H-pyrrol-2-yl)butyl]-1H-pyrrole-2-carbaldehyde
• 化学式: C₂₇H₄₈N₂O₃Si₂
• 分子量: 504.861
• InChiKey: XMTFNDCLYQMQHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  5-(4-nitrophenyl)-1,9-bis[(N-propylimino)methyl]dipyrromethane 、 甲酸苯酯 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 1.17h， 以57%的产率得到5-[1,5-bis(tert-butyldimethylsilyloxy)pent-3-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.