9-[4'-(13''-aza-1'',4'',7'',10''-tetraoxacyclopentadecan-13''-yl)benzylidene]-10-methylacridan | 1101052-77-0

• 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: 9-[4'-(13''-aza-1'',4'',7'',10''-tetraoxacyclopentadecan-13''-yl)benzylidene]-10-methylacridan
• 英文别名: 13-[4-[(10-Methylacridin-9-ylidene)methyl]phenyl]-1,4,7,10-tetraoxa-13-azacyclopentadecane
• CAS: 1101052-77-0
• 化学式: C₃₁H₃₆N₂O₄
• 分子量: 500.638
• InChiKey: IKCSIZCNZITOCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  69 °C
• 沸点：
  668.5±55.0 °C(predicted)
• 密度：
  1.135±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9-diethylphosphono-10-methylacridan 、 4-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-benzaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以93%的产率得到9-[4'-(13''-aza-1'',4'',7'',10''-tetraoxacyclopentadecan-13''-yl)benzylidene]-10-methylacridan
  参考文献：
  名称：

  Toward a Chemiluminescent Molecular Device: Metal Ion-Enhanced Chemiluminescence of Benzylidenacridan with 15-Monoazacrown-5

  摘要：

  The benzylidenacridans (1a-d) with one or more methoxy groups emit light from the excited N-methylacridone (NMA) when treated with a solution of sodium hypochlorite and alkaline hydrogen peroxide, in which a Hammett relationship with a negative rho value was applied between the chemiluminescence quantum yields and the sigma values. However, the dimethylamino group drastically inhibited the chemiluminescence in spite of its low sigma value. While the compound (2) with 15-monoazacrown-5 also showed a very weak chemiluminescence upon treatment with tetrabutylammonium hydroxide and hydrogen peroxide in acetonitrile, the chemiluminescence was enhanced up to 20 times in efficiency when divalent metal cations, such as magnesium and calcium ions, were added. The chemiluminescence inhibition is proved to be due to the shortening of the fluorescence lifetime of NMA due to energy dissipation by the amino substituents, but the incorporation of calcium ion into the cavity of the azacrown significantly prolonged the lifetime. Thus, the possibility of metal ion sensing by a chemiluminescent molecular device is suggested.

  DOI：

  10.1021/jo801556p

文献信息

• Toward a Chemiluminescent Molecular Device: Metal Ion-Enhanced Chemiluminescence of Benzylidenacridan with 15-Monoazacrown-5
  作者：Jiro Motoyoshiya、Toshimitsu Tanaka、Motoki Kuroe、Yoshinori Nishii

  DOI：10.1021/jo801556p

  日期：2009.2.6

  The benzylidenacridans (1a-d) with one or more methoxy groups emit light from the excited N-methylacridone (NMA) when treated with a solution of sodium hypochlorite and alkaline hydrogen peroxide, in which a Hammett relationship with a negative rho value was applied between the chemiluminescence quantum yields and the sigma values. However, the dimethylamino group drastically inhibited the chemiluminescence in spite of its low sigma value. While the compound (2) with 15-monoazacrown-5 also showed a very weak chemiluminescence upon treatment with tetrabutylammonium hydroxide and hydrogen peroxide in acetonitrile, the chemiluminescence was enhanced up to 20 times in efficiency when divalent metal cations, such as magnesium and calcium ions, were added. The chemiluminescence inhibition is proved to be due to the shortening of the fluorescence lifetime of NMA due to energy dissipation by the amino substituents, but the incorporation of calcium ion into the cavity of the azacrown significantly prolonged the lifetime. Thus, the possibility of metal ion sensing by a chemiluminescent molecular device is suggested.