1,11-bis(4-methylcoumarin-7-yl)-6-methyl-1,3,6,9,11-pentaazaundeca-2,10-dione | 1374840-79-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 1,11-bis(4-methylcoumarin-7-yl)-6-methyl-1,3,6,9,11-pentaazaundeca-2,10-dione
• 英文别名: 1-[2-[Methyl-[2-[(4-methyl-2-oxochromen-7-yl)carbamoylamino]ethyl]amino]ethyl]-3-(4-methyl-2-oxochromen-7-yl)urea；1-[2-[methyl-[2-[(4-methyl-2-oxochromen-7-yl)carbamoylamino]ethyl]amino]ethyl]-3-(4-methyl-2-oxochromen-7-yl)urea
• CAS: 1374840-79-5
• 化学式: C₂₇H₂₉N₅O₆
• 分子量: 519.557
• InChiKey: NTKSVUDEVBNAIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-methyl-3-azapentane-1,5-diamine * 3HCl 、 4-itrophenyl N-(4-methyl-2-oxo-2H-chromen-7-yl)carbamate 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以78%的产率得到1,11-bis(4-methylcoumarin-7-yl)-6-methyl-1,3,6,9,11-pentaazaundeca-2,10-dione
  参考文献：
  名称：

  New coumarin-urea based receptor for anions: a selective off–on fluorescence response to fluoride

  摘要：

  A novel fluorosensor for anions, 1,11-bis(4-methylcoumarin-7-yl)-6-methyl-1,3,6,9,11-pentaazaundeca-2,10-dione (L), which contains two coumarin-urea units spaced by a flexible diethylenetriamine fragment, was easily prepared in 65% yield by a one-pot two-step procedure. The binding ability of L toward several anions (G) was evaluated by H-1 NMR, UV-vis, and fluorescence titration. It was found that L forms stable [LG] and [LG(2)] species in both DMSO and CH3CN solvents. Furthermore, the fluorescence emission of L in the visible range (400 nm) is affected by the presence of anions; it is quenched by acetate, chloride, and pyrophosphate while it is enhanced by fluoride. Thus, this novel fluorosensor provides a selective off-on response to the presence of fluoride in solution. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.067

文献信息

• New coumarin-urea based receptor for anions: a selective off–on fluorescence response to fluoride
  作者：Gianluca Ambrosi、Mauro Formica、Vieri Fusi、Luca Giorgi、Eleonora Macedi、Giovanni Piersanti、Michele Retini、Maria Antonietta Varrese、Giovanni Zappia

  DOI：10.1016/j.tet.2012.02.067

  日期：2012.5

  A novel fluorosensor for anions, 1,11-bis(4-methylcoumarin-7-yl)-6-methyl-1,3,6,9,11-pentaazaundeca-2,10-dione (L), which contains two coumarin-urea units spaced by a flexible diethylenetriamine fragment, was easily prepared in 65% yield by a one-pot two-step procedure. The binding ability of L toward several anions (G) was evaluated by H-1 NMR, UV-vis, and fluorescence titration. It was found that L forms stable [LG] and [LG(2)] species in both DMSO and CH3CN solvents. Furthermore, the fluorescence emission of L in the visible range (400 nm) is affected by the presence of anions; it is quenched by acetate, chloride, and pyrophosphate while it is enhanced by fluoride. Thus, this novel fluorosensor provides a selective off-on response to the presence of fluoride in solution. (C) 2012 Elsevier Ltd. All rights reserved.