3,3'-Dimethylene-2,2'-bibenzoquinoline | 154845-29-1

• 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: 3,3'-Dimethylene-2,2'-bibenzoquinoline
• 英文别名: 3,3'-dimethylene-2,2'-bibenzo[g]quinoline；3,30-Diazaheptacyclo[16.12.0.02,15.04,13.06,11.020,29.022,27]triaconta-1(30),2,4,6,8,10,12,14,18,20,22,24,26,28-tetradecaene
• CAS: 154845-29-1
• 化学式: C₂₈H₁₈N₂
• 分子量: 382.464
• InChiKey: DPUVOGFKSPQGQY-UHFFFAOYSA-N

物化性质

• 沸点：
  673.6±35.0 °C(predicted)
• 密度：
  1.323±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 水合三氯化钌 、 3,3'-Dimethylene-2,2'-bibenzoquinoline 以 水 、 乙二醇 为溶剂， 以19%的产率得到[Ru(3,3'-dimethylene-2,2'-bibenzo[g]quinoline)3](PF6)2
  参考文献：
  名称：

  Ru(II) complexes of crowded delocalized diimine ligands

  摘要：

  The ligands 3,3'-dimethylene-2,2'-bibenzo[g]quinoline and bisbenzo[2,3:9,8]-1,10-phenanthroline have been coordinated with Ru(II) to form both tris- and mixed ligand complexes. These species are highly congested about the metal center but can be formed through the use of microwave irradiation. Shielding and deshielding effects on the chemical shifts of the aryl as well as the bridge protons reveal important conformational effects. Bathochromic shifts are observed in the electronic absorption spectra, associated with increased delocalization of the ligand and lowering of the pi*-energy level. Similar effects are observed for the reduction potentials while the oxidation potentials are much less sensitive to ligand structure. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(01)00684-3
• 作为产物：
  描述：

  1,2-环己二酮 、 3-氨基萘-2-甲醛 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以58%的产率得到3,3'-Dimethylene-2,2'-bibenzoquinoline
  参考文献：
  名称：

  Synthesis and Properties of Ligands Based on Benzo[g]quinoline

  摘要：

  The preparation of 3-amino-2-naphthaldehyde is described. Ammonolysis of 3-hydroxy-8-naphthoic acid affords the corresponding amino acid which can be esterified and then reduced with LAH. Protection of the amino group, MnO2 oxidation of the primary alcohol to an aldehyde, and deprotection gave the amino aldehyde which is an excellent Friedlander synthon for benzo[g]quinolines. Dimethylene-bridged analogues of 2,2'-bipyridine and 2,2';6,2''-terpyridine were prepared as well as orthocyclophanes derived from tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione (TCU-2,7-dione). The absorption and emission spectra of these species are consistent with the parent benzo[g]quinoline where bathochromic shifts result from increased delocalization. The TCU derivative evidences exciplex formation so that its benzo[g]quinoline emission is almost completely quenched and an exciplex emission appears at 525 nm. Electrochemical analysis indicates that both reduction and UV absorption involve the same pi(*) orbital.

  DOI：

  10.1021/jo00083a024

文献信息

• Synthesis and Properties of Ligands Based on Benzo[g]quinoline
  作者：Emmanuelle Taffarel、Sarah Chirayil、Randolph P. Thummel

  DOI：10.1021/jo00083a024

  日期：1994.2

  The preparation of 3-amino-2-naphthaldehyde is described. Ammonolysis of 3-hydroxy-8-naphthoic acid affords the corresponding amino acid which can be esterified and then reduced with LAH. Protection of the amino group, MnO2 oxidation of the primary alcohol to an aldehyde, and deprotection gave the amino aldehyde which is an excellent Friedlander synthon for benzo[g]quinolines. Dimethylene-bridged analogues of 2,2'-bipyridine and 2,2';6,2''-terpyridine were prepared as well as orthocyclophanes derived from tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione (TCU-2,7-dione). The absorption and emission spectra of these species are consistent with the parent benzo[g]quinoline where bathochromic shifts result from increased delocalization. The TCU derivative evidences exciplex formation so that its benzo[g]quinoline emission is almost completely quenched and an exciplex emission appears at 525 nm. Electrochemical analysis indicates that both reduction and UV absorption involve the same pi(*) orbital.
• Ru(II) complexes of crowded delocalized diimine ligands
  作者：Feiyue Wu、Randolph P Thummel

  DOI：10.1016/s0020-1693(01)00684-3

  日期：2002.1

  The ligands 3,3'-dimethylene-2,2'-bibenzo[g]quinoline and bisbenzo[2,3:9,8]-1,10-phenanthroline have been coordinated with Ru(II) to form both tris- and mixed ligand complexes. These species are highly congested about the metal center but can be formed through the use of microwave irradiation. Shielding and deshielding effects on the chemical shifts of the aryl as well as the bridge protons reveal important conformational effects. Bathochromic shifts are observed in the electronic absorption spectra, associated with increased delocalization of the ligand and lowering of the pi*-energy level. Similar effects are observed for the reduction potentials while the oxidation potentials are much less sensitive to ligand structure. (C) 2002 Elsevier Science B.V. All rights reserved.