Ethyl 2H-dibenzoisoindole-1-carboxylate | 144991-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: Ethyl 2H-dibenzoisoindole-1-carboxylate
• 英文别名: ethyl 7,8-diazaphenanthro[9,10-c]pyrrole-1-carboxylate；ethyl 2H-pyrrolo[3,4-f][1,10]phenanthroline-3-carboxylate
• CAS: 144991-44-6
• 化学式: C₁₇H₁₃N₃O₂
• 分子量: 291.309
• InChiKey: YECZJLYWNUWMMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Ethyl 2H-dibenzoisoindole-1-carboxylate 在 氢氧化钾 作用下， 以 乙二醇 为溶剂， 以92%的产率得到7,8-diazaphenanthro[9,10-c]pyrrole
  参考文献：
  名称：

  通过“ 3 +1”方法合成卟啉：一种制备具有融合的9,10-菲咯啉亚基的卟啉的高级方法

  摘要：

  带有1,10-菲咯啉亚基稠合的卟啉已通过酸催化菲咯啉取代的三吡喃与2,5-吡咯烷二醛的缩合反应以极高的产率制备。

  DOI：

  10.1016/0040-4039(95)02100-0
• 作为产物：
  描述：

  异氰基乙酸乙酯 、 5-硝基-1,10-菲咯啉 生成 Ethyl 2H-dibenzoisoindole-1-carboxylate
  参考文献：
  名称：

  通过“ 3 +1”方法合成卟啉：一种制备具有融合的9,10-菲咯啉亚基的卟啉的高级方法

  摘要：

  带有1,10-菲咯啉亚基稠合的卟啉已通过酸催化菲咯啉取代的三吡喃与2,5-吡咯烷二醛的缩合反应以极高的产率制备。

  DOI：

  10.1016/0040-4039(95)02100-0

文献信息

• Porphyrin synthesis by the “3 + 1” methodology: A superior approach for the preparation of porphyrins with fused 9,10-phenanthroline subunits
  作者：Vanning Lin、Timothy D. Lash

  DOI：10.1016/0040-4039(95)02100-0

  日期：1995.12

  Porphyrins with fused 1,10-phenanthroline subunits have been prepared in exceptionally high yields by the acid catalyzed condensation of phenanthroline substituted tripyrranes with a 2,5-pyrroledicarboxaldehyde.

  带有1,10-菲咯啉亚基稠合的卟啉已通过酸催化菲咯啉取代的三吡喃与2,5-吡咯烷二醛的缩合反应以极高的产率制备。
• Synthesis of pyrroles annulated with polycyclic aromatic compounds; precursor molecules for low band gap polymers
  作者：Noboru Ono、Hideo Hironaga、Kazuhiro Simizu、Kazuo Ono、Kayoko Kuwano、Takuji Ogawa

  DOI：10.1039/c39940001019

  日期：——

  Pyrroles annulated with polycyclic aromatic compounds, which are expected to be good precursor molecules for low band gap polymers, are prepared by the reaction of aromatic nitro compounds with ethyl isocyanoacetate and the subsequent deethoxycarbonylation.

  通过芳族硝基化合物与异氰基乙酸乙酯反应，然后进行脱乙氧基羰基化反应，可以制备与多环芳族化合物环合的吡咯，这些环对于低带隙聚合物而言是很好的前体分子。
• A new synthesis of pyrroles and porphyrins fused with aromatic rings
  作者：Noboru Ono、Hideo Hironaga、Kazuo Ono、Syunichi Kaneko、Takashi Murashima、Takahiro Ueda、Chikanori Tsukamura、Takuji Ogawa

  DOI：10.1039/p19960000417

  日期：——

  aromatics such as nitrobenzene or nitronaphthalenes and give the corresponding pyrroles in good yields. Pyrroles prepared by this method have been converted into porphyrins fused with various aromatic rings by the reduction with LiAlH4 followed by treatment with an acid catalyst and oxidation with chloranil or oxygen. Tetra-1,2-naphthoporphyrin has been prepared by the reaction of 2-nitro-3,4-dihydronaphthalene

  通过在DBU存在下使芳族硝基化合物与异氰基乙酸乙酯反应，可以容易地制备与芳环稠合的吡咯。该反应的容易程度取决于起始硝基芳族化合物的芳族性。多环芳族硝基化合物（例如1-硝基or或9-硝基菲）比简单的硝基芳族化合物（例如硝基苯或硝基萘）具有更高的反应性，并能以高收率得到相应的吡咯。通过LiAlH 4还原，已将通过该方法制备的吡咯转化为与各种芳环稠合的卟啉然后用酸催化剂处理，并用氯乙腈或氧气氧化。通过使2-硝基-3,4-二氢萘或1-硝基萘与异氰基乙酸乙酯反应，然后还原，四聚和氧化反应，可制得1，4-萘卟啉。因此，容易从芳族硝基化合物开始制备高度共轭的卟啉，并且可以通过选择起始芳族硝基化合物来控制它们的电子和光学性质。
• Novel metal-coordinated 1,10-phenanthroline ligands functionalized with a lactam or imide
  作者：Hao Yao、Lilu Zhang、Yanqiu Peng、Patrick J. Carroll、Lei Gong、Eric Meggers

  DOI：10.1016/j.ica.2014.07.008

  日期：2014.9
• Porphyrins with exocyclic rings. Part 19: Efficient syntheses of phenanthrolinoporphyrins
  作者：Timothy D. Lash、Yanning Lin、Bennett H. Novak、Mihir D. Parikh

  DOI：10.1016/j.tet.2005.09.089

  日期：2005.12

  5-Nitro-1,10-phenanthrolines react with isocyanoacetate esters in the presence of DBU in THF to give excellent yields of the corresponding phenanthrolinopyrroles. These were condensed with acetoxymethylpyrroles using catalytic quantities Of p-tolenesulfonic acid in acetic acid to give dipyrrylmethanes, but these structures proved to be poorly suited for porphyrin synthesis due to the electron-withdrawing nature of the fused phenanthroline unit. However, phenanthrolinopyrrole ethyl esters could be converted to the corresponding alpha-unsubstituted pyrroles with KOH in ethylene glycol at 180-190 degrees C and these condensed with 2 equiv of acetoxymethylpyrroles in refluxing acetic acid-isopropyl alcohol to give tripyrranes. In a one pot procedure, tripyrrane di-tert-butyl esters were treated with TFA at room temperature to cleave the protective groups, diluted with dichloromethane, reacted with pyrrole dialdehydes and oxidized to afford phenanthrolinoporphyrins in 52-83% yield. These conditions also allow the synthesis of porphyrins with additional fused acenaphthylene or phenanthrene rings. Although the UV-vis spectra for these porphyrins are unexceptional, the presence of an external coordination site allows many potential applications to be considered. Porphyrins with two phenanthroline units could not be prepared by the '3 + 11 strategy. Instead, alpha-unsubstituted phenanthrolinopyrroles were reacted with a bis(dimethylaminomethyl)pyrrole in refluxing acetic acid to give moderate yields of the corresponding opp-diphenanthrolinoporphyrins. In one case, a triphenanthrolitioporphyrin and trace amounts of an adj-diphenanthrolinoporphyrin were formed as by-products. (c) 2005 Elsevier Ltd. All rights reserved.