bis-1,3-(5-tert-butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolylmethyl)isoquino[5,6-c]pyrrole | 312273-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: bis-1,3-(5-tert-butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolylmethyl)isoquino[5,6-c]pyrrole
• 英文别名: tert-butyl 4-ethyl-5-[[1-[[3-ethyl-4-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-1H-pyrrol-2-yl]methyl]-2H-pyrrolo[3,4-f]isoquinolin-3-yl]methyl]-3-methyl-1H-pyrrole-2-carboxylate
• CAS: 312273-75-9
• 化学式: C₃₇H₄₆N₄O₄
• 分子量: 610.797
• InChiKey: SDCZNDQEXUHNSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-二乙基-1H-吡咯-2,5-二羧醛 、 bis-1,3-(5-tert-butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolylmethyl)isoquino[5,6-c]pyrrole 在 三氟乙酸 、 三乙胺 、 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 4.0h， 以81%的产率得到7,12,13,18-tetraethyl-8,17-dimethylisoquino[5,6-b]porphyrin
  参考文献：
  名称：

  Porphyrins with Exocyclic Rings. 15.¹ Synthesis of Quino- and Isoquinoporphyrins, Aza Analogues of the Naphthoporphyrins

  摘要：

  Porphyrins with fused isoquinoline and quinoline units have been prepared by the "3 +/- 1" methodology. 5-Nitroisoquinoline and 6-nitroquinoline condensed with ethyl isocyanoacetate in the presence of a phosphazene base to give isoquino- and quinopyrroles, respectively. Ester saponification and decarboxylation with KOH in ethylene glycol at 190 degreesC gave the parent azatricycles, and these were further condensed with 2 equiv of an acetoxymethylpyrrole to give the corresponding tripyrranes protected at the terminal positions as their tert-butyl esters. In a one-pot procedure, the ester protective groups were cleaved with TFA, and following dilution with dichloromethane, "3 + 1" condensation with a pyrrole dialdehyde and dehydrogenation of the phlorin intermediate with DDQ gave the targeted azanaphthoporphyrins in excellent yields. Although the UV-vis spectra of these new porphyrin systems are unexceptional, they show promise for further functionalization and applications in the development of porphyrin arrays. In addition, a zinc chelate of the isoquinoporphyrin system shows a high degree of regioselective intermolecular interaction/aggregation in chloroform solution that may lead to selectivity in molecular recognition studies.

  DOI：

  10.1021/jo001216m
• 作为产物：
  描述：

  ethyl isoquino[5,6-c]pyrrole-3-carboxylate 在 氢氧化钾 、 肼 作用下， 以 乙二醇 、 溶剂黄146 、 异丙醇 为溶剂， 反应 16.5h， 生成 bis-1,3-(5-tert-butoxycarbonyl-3-ethyl-4-methyl-2-pyrrolylmethyl)isoquino[5,6-c]pyrrole
  参考文献：
  名称：

  Porphyrins with Exocyclic Rings. 15.¹ Synthesis of Quino- and Isoquinoporphyrins, Aza Analogues of the Naphthoporphyrins

  摘要：

  Porphyrins with fused isoquinoline and quinoline units have been prepared by the "3 +/- 1" methodology. 5-Nitroisoquinoline and 6-nitroquinoline condensed with ethyl isocyanoacetate in the presence of a phosphazene base to give isoquino- and quinopyrroles, respectively. Ester saponification and decarboxylation with KOH in ethylene glycol at 190 degreesC gave the parent azatricycles, and these were further condensed with 2 equiv of an acetoxymethylpyrrole to give the corresponding tripyrranes protected at the terminal positions as their tert-butyl esters. In a one-pot procedure, the ester protective groups were cleaved with TFA, and following dilution with dichloromethane, "3 + 1" condensation with a pyrrole dialdehyde and dehydrogenation of the phlorin intermediate with DDQ gave the targeted azanaphthoporphyrins in excellent yields. Although the UV-vis spectra of these new porphyrin systems are unexceptional, they show promise for further functionalization and applications in the development of porphyrin arrays. In addition, a zinc chelate of the isoquinoporphyrin system shows a high degree of regioselective intermolecular interaction/aggregation in chloroform solution that may lead to selectivity in molecular recognition studies.

  DOI：

  10.1021/jo001216m

文献信息

• Porphyrins with Exocyclic Rings. 15.¹ Synthesis of Quino- and Isoquinoporphyrins, Aza Analogues of the Naphthoporphyrins
  作者：Timothy D. Lash、Virajkumar Gandhi

  DOI：10.1021/jo001216m

  日期：2000.11.1

  Porphyrins with fused isoquinoline and quinoline units have been prepared by the "3 +/- 1" methodology. 5-Nitroisoquinoline and 6-nitroquinoline condensed with ethyl isocyanoacetate in the presence of a phosphazene base to give isoquino- and quinopyrroles, respectively. Ester saponification and decarboxylation with KOH in ethylene glycol at 190 degreesC gave the parent azatricycles, and these were further condensed with 2 equiv of an acetoxymethylpyrrole to give the corresponding tripyrranes protected at the terminal positions as their tert-butyl esters. In a one-pot procedure, the ester protective groups were cleaved with TFA, and following dilution with dichloromethane, "3 + 1" condensation with a pyrrole dialdehyde and dehydrogenation of the phlorin intermediate with DDQ gave the targeted azanaphthoporphyrins in excellent yields. Although the UV-vis spectra of these new porphyrin systems are unexceptional, they show promise for further functionalization and applications in the development of porphyrin arrays. In addition, a zinc chelate of the isoquinoporphyrin system shows a high degree of regioselective intermolecular interaction/aggregation in chloroform solution that may lead to selectivity in molecular recognition studies.