7,6-(2',3'-<1,8>naphthyridino)tetracyclo<6.3.0.04,11.05,9>undecane-2-one | 131251-68-8

• 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: 7,6-(2',3'-<1,8>naphthyridino)tetracyclo<6.3.0.04,11.05,9>undecane-2-one
• 英文别名: 7,6-(2',3'-<1,8>naphthyridino)tetracyclo<6.3.0.0^4,11.0^5,9>undecane-2-one
• CAS: 131251-68-8
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: RSMRHMRWHBDRGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  42.85
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7,6-(2',3'-<1,8>naphthyridino)tetracyclo<6.3.0.04,11.05,9>undecane-2-one 、 2-氨基苯甲醛 在 氢氧化钾 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 16.0h， 以40%的产率得到2,3-(2',3'-quinolino)-7,6-(2'',3''-<1,8>naphthyridino)tetracyclo<6.3.0.0^4,11.0^5,9>undecane
  参考文献：
  名称：

  Heteroaromatic fused derivatives of tetracyclo[6.3.0.04,11.O5,9]undecane

  摘要：

  A series of rigid syn-orthocyclophanes is prepared by the Friedlander condensation of appropriate o-amino-benzaldehyde derivatives with tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione. The reaction may proceed in a stepwise fashion so that unsymmetrical layered compounds can be prepared. These species can be further elaborated by oxidation to quinolinequinones or N-oxides and quaternization to quinolinium salts. Molecular mechanics calculations agree closely with X-ray analysis in describing the structural properties of these cyclophanes. Analysis of the H-1 NMR and UV spectra as well as the reduction potentials of these molecules support a moderate electronic interaction between the decks. Initial investigations regarding their ability to serve as cleft-type hosts are described.

  DOI：

  10.1021/jo00004a029
• 作为产物：
  描述：

  2-氨基-3-吡啶甲醛 、 tetracyclo<6.3.0.0^4,11,0^5,9>undecane-2,6-dione 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以50%的产率得到7,6-(2',3'-<1,8>naphthyridino)tetracyclo<6.3.0.04,11.05,9>undecane-2-one
  参考文献：
  名称：

  Heteroaromatic fused derivatives of tetracyclo[6.3.0.04,11.O5,9]undecane

  摘要：

  A series of rigid syn-orthocyclophanes is prepared by the Friedlander condensation of appropriate o-amino-benzaldehyde derivatives with tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione. The reaction may proceed in a stepwise fashion so that unsymmetrical layered compounds can be prepared. These species can be further elaborated by oxidation to quinolinequinones or N-oxides and quaternization to quinolinium salts. Molecular mechanics calculations agree closely with X-ray analysis in describing the structural properties of these cyclophanes. Analysis of the H-1 NMR and UV spectra as well as the reduction potentials of these molecules support a moderate electronic interaction between the decks. Initial investigations regarding their ability to serve as cleft-type hosts are described.

  DOI：

  10.1021/jo00004a029