tetracyclo<6.3.0.0^4,11.0^5,9>undecane-6-en-2-one | 58228-96-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tetracyclo<6.3.0.0^4,11.0^5,9>undecane-6-en-2-one
• 英文别名: Tetracyclo<6.3.0.0^4,11.0^5.9>-undec-6-en-2-on；1,2,3,3a,4,6a-Hexahydro-2,4,1-(propane[1,1,3]triyl)pentalen-8-one；tetracyclo[6.3.0.02,6.05,9]undec-10-en-3-one
• CAS: 58228-96-9
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: QNAPZDCXGCMLPG-UHFFFAOYSA-N

物化性质

• 沸点：
  268.9±19.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-氨基-3-吡啶甲醛 、 tetracyclo<6.3.0.0^4,11.0^5,9>undecane-6-en-2-one 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以27%的产率得到2,3-(2',3'-<1,8>naphthyridino)tetracyclo<6.3.0.0^4,11.0^5,9>undecane-6-ene
  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

文献信息

• Ipaktschi, Junes; Herber, Juergen; Kalinowski, Hans-Otto, Chemische Berichte, 1990, vol. 123, # 2, p. 299 - 304
  作者：Ipaktschi, Junes、Herber, Juergen、Kalinowski, Hans-Otto、Amme, Monika、Boese, Roland

  DOI：——

  日期：——
• LIM, JEAN-LUC;CHIRAYIL, SARA;THUMMEL, RANDOLPH P., J. ORG. CHEM., 56,(1991) N, C. 1492-1500
  作者：LIM, JEAN-LUC、CHIRAYIL, SARA、THUMMEL, RANDOLPH P.

  DOI：——

  日期：——
• Heteroaromatic fused derivatives of tetracyclo[6.3.0.04,11.O5,9]undecane
  作者：Jean Luc Lim、Sara Chirayil、Randolph P. Thummel

  DOI：10.1021/jo00004a029

  日期：1991.2

  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.