1,9-bis(N,N-dimethylaminomethyl)-5-(5,5-dimethyl-1,3-dioxan-2-yl)dipyrromethane | 869193-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1,9-bis(N,N-dimethylaminomethyl)-5-(5,5-dimethyl-1,3-dioxan-2-yl)dipyrromethane
• CAS: 869193-04-4
• 化学式: C₂₁H₃₄N₄O₂
• 分子量: 374.527
• InChiKey: MGCOPRAUGUFQKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  56.52
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,9-bis(N,N-dimethylaminomethyl)-5-(5,5-dimethyl-1,3-dioxan-2-yl)dipyrromethane 、 5-(4-methylphenyl)dipyrromethane 在 air 、 zinc diacetate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 为溶剂， 反应 2.25h， 以10%的产率得到zinc(II)-5-(5,5-dimethyl-1,3-dioxan-2-yl)-15-(4-methylphenyl)porphyrin
  参考文献：
  名称：

  1,9-Bis(N,N-dimethylaminomethyl)dipyrromethanes in the synthesis of porphyrins bearing one or two meso substituents

  摘要：

  A synthesis of 5,15-disubstituted zinc-porphyrins has been developed that employs condensation of a 1,9-bis(N,N-dimethylaminomethyl)dipyrromethane+a dipyrromethane in refluxing ethanol containing zinc acetate followed by oxidation with DDQ. The NN-dimethylaminomethylation of the dipyrromethane was achieved via Eschenmoser's reagent (N,N-dimethylmethyleneammonium iodide) in CH2Cl2 at room temperature. The synthesis is compatible with diverse substituents (e.g., alkyl, aryl, ester, acetal) and enables rapid synthesis of trans-AB-, A(2)-, and A-porphyrins. The synthesis of > 40 zinc porphyrins has been surveyed; 13 zinc porphyrins were isolated in yields of 5-20% without detectable scrambling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.028
• 作为产物：
  描述：

  2-formyl-5,5-dimethyl-1,3-dioxane 在 indium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,9-bis(N,N-dimethylaminomethyl)-5-(5,5-dimethyl-1,3-dioxan-2-yl)dipyrromethane
  参考文献：
  名称：

  1,9-Bis(N,N-dimethylaminomethyl)dipyrromethanes in the synthesis of porphyrins bearing one or two meso substituents

  摘要：

  A synthesis of 5,15-disubstituted zinc-porphyrins has been developed that employs condensation of a 1,9-bis(N,N-dimethylaminomethyl)dipyrromethane+a dipyrromethane in refluxing ethanol containing zinc acetate followed by oxidation with DDQ. The NN-dimethylaminomethylation of the dipyrromethane was achieved via Eschenmoser's reagent (N,N-dimethylmethyleneammonium iodide) in CH2Cl2 at room temperature. The synthesis is compatible with diverse substituents (e.g., alkyl, aryl, ester, acetal) and enables rapid synthesis of trans-AB-, A(2)-, and A-porphyrins. The synthesis of > 40 zinc porphyrins has been surveyed; 13 zinc porphyrins were isolated in yields of 5-20% without detectable scrambling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.028