5-[[5-[[5-carboxy-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-3,4-diphenyl-1H-pyrrol-2-yl]methyl]-4-(3-methoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2-carboxylic acid | 1025914-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-[[5-[[5-carboxy-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-3,4-diphenyl-1H-pyrrol-2-yl]methyl]-4-(3-methoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 1025914-22-0
• 化学式: C₃₈H₃₉N₃O₈
• 分子量: 665.743
• InChiKey: ACZFNMCJNLDPDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  175
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5-bis(N,N-dimethylaminomethyl)-3,4-diethylpyrrole 、 5-[[5-[[5-carboxy-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-3,4-diphenyl-1H-pyrrol-2-yl]methyl]-4-(3-methoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2-carboxylic acid 在 potassium hexacyanoferrate(III) 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以31%的产率得到17,18-diethyl-3,12-bis<2-(methoxycarbonyl)ethyl>-2,13-dimethyl-7,8-diphenylporphyrin
  参考文献：
  名称：

  Simple Methodology for Syntheses of Porphyrins Possessing Multiple Peripheral Substituents with an Element of Symmetry

  摘要：

  New methodology was developed for synthesis of regiochemically pure porphyrins with D-2h symmetry (e.g. 9) via tetramerization reactions involving two different pyrroles. The two pyrrole components were a 2,5-diunsubstituted pyrrole (e.g. 11) and a 2,5-bis[(N,N-dimethylamino)methyl]pyrrole (e.g, 10), the latter being formed from a 2,5-di-unsubstituted pyrrole by treatment with excess Eschenmoser's reagent (N,N-dimethylmethyleneammonium iodide). A bis-butanoporphyrin 16 was transformed into the corresponding opp-bis-benzoporphyrin 17 by treatment with DDQ. The synthetic method was further extended to allow the synthesis of more unsymmetrical porphyrins, with C-2v symmetry (e.g. 32), by reacting a tripyrrane (e.g. 27) with a 2,5-bis[(N,N-dimethylamino)methyl]pyrrole (e.g. 18). The structures and substituent arrays in both type of porphyrins were confirmed by single-crystal X-ray crystallography.

  DOI：

  10.1021/jo951870f
• 作为产物：
  描述：

  3,4-二苯基-1H-吡咯 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 22.0h， 生成 5-[[5-[[5-carboxy-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-3,4-diphenyl-1H-pyrrol-2-yl]methyl]-4-(3-methoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Simple Methodology for Syntheses of Porphyrins Possessing Multiple Peripheral Substituents with an Element of Symmetry

  摘要：

  New methodology was developed for synthesis of regiochemically pure porphyrins with D-2h symmetry (e.g. 9) via tetramerization reactions involving two different pyrroles. The two pyrrole components were a 2,5-diunsubstituted pyrrole (e.g. 11) and a 2,5-bis[(N,N-dimethylamino)methyl]pyrrole (e.g, 10), the latter being formed from a 2,5-di-unsubstituted pyrrole by treatment with excess Eschenmoser's reagent (N,N-dimethylmethyleneammonium iodide). A bis-butanoporphyrin 16 was transformed into the corresponding opp-bis-benzoporphyrin 17 by treatment with DDQ. The synthetic method was further extended to allow the synthesis of more unsymmetrical porphyrins, with C-2v symmetry (e.g. 32), by reacting a tripyrrane (e.g. 27) with a 2,5-bis[(N,N-dimethylamino)methyl]pyrrole (e.g. 18). The structures and substituent arrays in both type of porphyrins were confirmed by single-crystal X-ray crystallography.

  DOI：

  10.1021/jo951870f