phenyl-bis(3-formyl-4,5,6,7-tetrahydro-2H-isoindolyl)methane | 1029092-42-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: phenyl-bis(3-formyl-4,5,6,7-tetrahydro-2H-isoindolyl)methane
• CAS: 1029092-42-9
• 化学式: C₂₅H₂₆N₂O₂
• 分子量: 386.494
• InChiKey: VEKFNSAGQVDMNX-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  、 phenyl-bis(3-formyl-4,5,6,7-tetrahydro-2H-isoindolyl)methane 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以20%的产率得到5,15-diphenyltetracyclohexenoporphyrin
  参考文献：
  名称：

  Synthesis of 5,15-Diaryltetrabenzoporphyrins

  摘要：

  A general method of synthesis of 5,15-diaryltetrabenzoporphyrins (Ar(2)TBPs) has been developed, based on 2 + 2 condensation of dipyrromethanes followed by oxidative aromatization. Two pathways to Ar(2)TBPs were investigated: the tetrahydroisoindole pathway and the dihydroisoindole pathway. In the tetrahydroisoindole pathway, precursor 5,15-diaryltetracyclohexenoporphyrins (5,15-Ar(2)TCHPs) were assembled from cyclohexeno-fused meso-unsubstituted dipyrromethanes and aromatic aldehydes or, alternatively, by way of the classical MacDonald synthesis. In the first case, scrambling was observed. Aromatization by tetracyclone was more effective than aromatization by DDQ but failed in the cases of porphyrins with electron-withdrawing substituents in the meso-aryl rings. The dihydroisoindole pathway was found to be much superior to the tetrahydroisoindole pathway, and it was developed into a general preparative method, consisting of (1) the synthesis of 4,7-dihydroisoindole and its transformation into meso-unsubstituted dipyrromethanes, (2) the synthesis of 5,15-diaryloctahydrotetrabenzoporphyrins (5,15-Ar(2)OHTBPs), and (3) their subsequent aromatization by DDQ. Ar2TBP free bases exhibit optical absorption spectra similar to those of meso-unsubstituted tetrabenzoporphyrins and fluoresce with high quantum yields. Pd complex of Ph2TBP was found to be highly phosphorescent at room temperature.

  DOI：

  10.1021/jo800509k
• 作为产物：
  描述：

  、 原甲酸三甲酯 反应 0.25h， 以0.46 g的产率得到phenyl-bis(3-formyl-4,5,6,7-tetrahydro-2H-isoindolyl)methane
  参考文献：
  名称：

  Synthesis of 5,15-Diaryltetrabenzoporphyrins

  摘要：

  A general method of synthesis of 5,15-diaryltetrabenzoporphyrins (Ar(2)TBPs) has been developed, based on 2 + 2 condensation of dipyrromethanes followed by oxidative aromatization. Two pathways to Ar(2)TBPs were investigated: the tetrahydroisoindole pathway and the dihydroisoindole pathway. In the tetrahydroisoindole pathway, precursor 5,15-diaryltetracyclohexenoporphyrins (5,15-Ar(2)TCHPs) were assembled from cyclohexeno-fused meso-unsubstituted dipyrromethanes and aromatic aldehydes or, alternatively, by way of the classical MacDonald synthesis. In the first case, scrambling was observed. Aromatization by tetracyclone was more effective than aromatization by DDQ but failed in the cases of porphyrins with electron-withdrawing substituents in the meso-aryl rings. The dihydroisoindole pathway was found to be much superior to the tetrahydroisoindole pathway, and it was developed into a general preparative method, consisting of (1) the synthesis of 4,7-dihydroisoindole and its transformation into meso-unsubstituted dipyrromethanes, (2) the synthesis of 5,15-diaryloctahydrotetrabenzoporphyrins (5,15-Ar(2)OHTBPs), and (3) their subsequent aromatization by DDQ. Ar2TBP free bases exhibit optical absorption spectra similar to those of meso-unsubstituted tetrabenzoporphyrins and fluoresce with high quantum yields. Pd complex of Ph2TBP was found to be highly phosphorescent at room temperature.

  DOI：

  10.1021/jo800509k