2,5-bis[[5-carboxy-3-(2-methoxycarbonylethyl)-4-methyl-1H-pyrrol-2-yl]methyl]-3,4-dimethylpyrrole | 87260-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-bis[[5-carboxy-3-(2-methoxycarbonylethyl)-4-methyl-1H-pyrrol-2-yl]methyl]-3,4-dimethylpyrrole
• 英文别名: 5-[[5-[[5-carboxy-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-3,4-dimethyl-1H-pyrrol-2-yl]methyl]-4-(3-methoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 87260-13-7
• 化学式: C₂₈H₃₅N₃O₈
• 分子量: 541.601
• InChiKey: WFVLGKNLGNDLBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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[[5-carboxy-3-(2-methoxycarbonylethyl)-4-methyl-1H-pyrrol-2-yl]methyl]-3,4-dimethylpyrrole 在 strong acid H⁽¹⁺⁾ 、 氧气 、 氢气 作用下， 生成
  参考文献：
  名称：

  Macrocycles Containing Five Pyrrole Subunits: The Iso-oxopentaphyrin System

  摘要：

  DOI：

  10.3987/com-97-s(n)39
• 作为产物：
  描述：

  3,4-二甲基吡咯 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 2,5-bis[[5-carboxy-3-(2-methoxycarbonylethyl)-4-methyl-1H-pyrrol-2-yl]methyl]-3,4-dimethylpyrrole
  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

文献信息

• The synthesis of a new 22 π-electron macrocycle: pentaphyrin
  作者：Hans Rexhausen、Albert Gossauer

  DOI：10.1039/c39830000275

  日期：——

  The first synthesis of pentapyrrole macrocycle analogous to the porphyrins is described.

  描述了类似于卟啉的五吡咯大环的第一合成。
• Charriere, Roland; Jenny, Titus A.; Rexhausen, Hans, Heterocycles, 1993, vol. 36, # 7, p. 1561 - 1575
  作者：Charriere, Roland、Jenny, Titus A.、Rexhausen, Hans、Gossauer, Albert

  DOI：——

  日期：——
• Simple Methodology for Syntheses of Porphyrins Possessing Multiple Peripheral Substituents with an Element of Symmetry
  作者：Liem T. Nguyen、Mathias O. Senge、Kevin M. Smith

  DOI：10.1021/jo951870f

  日期：1996.1.1

  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.
• Macrocycles Containing Five Pyrrole Subunits: The Iso-oxopentaphyrin System
  作者：Kevin M. Smith、Richard G. Khoury、Laurent Jaquinod、Liem T. Nguyen

  DOI：10.3987/com-97-s(n)39

  日期：——