ethyl quino[5,6-c]pyrrole-1-carboxylate | 184584-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl quino[5,6-c]pyrrole-1-carboxylate
• 英文别名: ethyl 2H-pyrrolo[3,4-f]quinoline-1-carboxylate
• CAS: 184584-53-0
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: SMKVDJVLVMEPNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  471.4±25.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.98
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl quino[5,6-c]pyrrole-1-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)quino[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
• 作为产物：
  描述：

  6-硝基喹啉 、 异氰基乙酸乙酯 在 iminophosphorane 4 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以44%的产率得到ethyl quino[5,6-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  硝基杂芳族阴离子的环境反应性

  摘要：

  在1,8-二氮杂双环[5,4,0] undec -7-ene g存在下，两类硝基杂芳族化合物，如喹喔啉7a，b和7c，d与异氰基乙酸乙酯一起，给出了相应的嘧啶N-氧化物8a- d，与此相反，在相似条件下使用原氮杂磷杂环戊烷2或亚氨基正膦4作为碱，得到相应的吡咯9a-d。

  DOI：

  10.1016/0040-4039(96)01918-1

文献信息

• Synthesis of Novel Pyrrolic Compounds from Nitroarenes and Isocyanoacetates Using a Phosphazene Superbase
  作者：Timothy D. Lash、Michelle L. Thompson、Tonya M. Werner、John D. Spence

  DOI：10.1055/s-2000-6504

  日期：2000.2

  Utilization of a phosphazene base allows hitherto unreactive nitroaromatic compounds to condense with ethyl isocyanoacetate to give c-annelated pyrroles. On the other hand, 3-nitropyridine reacted under these conditions to give a novel tricyclic heterocycle 13 in modest yield.

  利用膦氮基能使迄今为止未发生反应的硝基芳香族化合物与异氰基乙酸乙酯发生缩合反应，生成 c-通道的吡咯。另一方面，3-硝基吡啶在这些条件下发生反应，生成了新颖的三环杂环 13，产率不高。
• Ambident reactivity of nitro heteroaromatic anions
  作者：Takashi Murashima、Ryuji Tamai、Ken-ichi Fujita、Hidemitsu Uno、Noboru Ono

  DOI：10.1016/0040-4039(96)01918-1

  日期：1996.11

  Two classes of nitro heteroaromatic compounds such as quinoxalines 7a,b and 7c,d with ethyl isocyanoacetate in the presence of 1,8-diazabicyclo[5,4,0]undec-7-ene g gave the corresponding pyrimidine N-oxides 8a-d, whilst, in contrast, use of proazaphosphatrane 2 or iminophosphorane 4 as a base under similar conditions gave the corresponding pyrroles 9a-d.

  在1,8-二氮杂双环[5,4,0] undec -7-ene g存在下，两类硝基杂芳族化合物，如喹喔啉7a，b和7c，d与异氰基乙酸乙酯一起，给出了相应的嘧啶N-氧化物8a- d，与此相反，在相似条件下使用原氮杂磷杂环戊烷2或亚氨基正膦4作为碱，得到相应的吡咯9a-d。
• 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.