3-dipicolylamine-N-(quinoline-8-yl)propanamide | 1415145-07-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-dipicolylamine-N-(quinoline-8-yl)propanamide
• 英文别名: 3-(bis(pyridin-2-ylmethyl)amino)-N-(quinolin-8-yl)propanamide；3-[bis(pyridin-2-ylmethyl)amino]-N-quinolin-8-ylpropanamide
• CAS: 1415145-07-1
• 化学式: C₂₄H₂₃N₅O
• 分子量: 397.48
• InChiKey: DIBAWASIZUCOMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-dipicolylamine-N-(quinoline-8-yl)propanamide 、 zinc(II) chloride 在 sodium iodide 作用下， 以 水 、 乙腈 为溶剂， 生成 zinc;3-[bis(pyridin-2-ylmethyl)amino]-N-quinolin-8-ylpropanamide;methanol;dichloride
  参考文献：
  名称：

  Zinc selective chemosensors based on the flexible dipicolylamine and quinoline

  摘要：

  Zinc sensor molecules containing quinoline have been synthesized, which show fluorescence in the presence of Zn2+. The nitrogen in quinoline is critical to fluorescence and fluorescence enhancement is promoted by deprotonating the sensor's amide. One of the sensors is highly selective for Zn2+ over Cd2+ and other cations such as Hg2+, Fe2+, Mn2+ and Ca2+. This selectivity can be attributed to the increased absorption of the sensor in the presence of Zn2+ and the strong binding of Zn2+. Structural studies, including X-ray and NMR, show the ability of dipicolylamine (DPA) to bind in facial and meridional manners to Zn2+. Crystal structures of different compounds show Zn2+ coordinating to three, four, and five nitrogens from the compounds. They also indicate that the selectivity of DPA containing compounds towards Zn2+ may originate from Zn2+ being stable in different coordination environments. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.09.009
• 作为产物：
  描述：

  3-chloro-N-(quinolin-8-yl)propanamide 、 二甲基吡啶胺 在 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以89.6%的产率得到3-dipicolylamine-N-(quinoline-8-yl)propanamide
  参考文献：
  名称：

  Zinc selective chemosensors based on the flexible dipicolylamine and quinoline

  摘要：

  Zinc sensor molecules containing quinoline have been synthesized, which show fluorescence in the presence of Zn2+. The nitrogen in quinoline is critical to fluorescence and fluorescence enhancement is promoted by deprotonating the sensor's amide. One of the sensors is highly selective for Zn2+ over Cd2+ and other cations such as Hg2+, Fe2+, Mn2+ and Ca2+. This selectivity can be attributed to the increased absorption of the sensor in the presence of Zn2+ and the strong binding of Zn2+. Structural studies, including X-ray and NMR, show the ability of dipicolylamine (DPA) to bind in facial and meridional manners to Zn2+. Crystal structures of different compounds show Zn2+ coordinating to three, four, and five nitrogens from the compounds. They also indicate that the selectivity of DPA containing compounds towards Zn2+ may originate from Zn2+ being stable in different coordination environments. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.09.009

文献信息

• Zinc selective chemosensors based on the flexible dipicolylamine and quinoline
  作者：Hong Gyu Lee、Ju Hoon Lee、Seung Pyo Jang、In Hong Hwang、Sung-Jin Kim、Youngmee Kim、Cheal Kim、Roger G. Harrison

  DOI：10.1016/j.ica.2012.09.009

  日期：2013.1

  Zinc sensor molecules containing quinoline have been synthesized, which show fluorescence in the presence of Zn2+. The nitrogen in quinoline is critical to fluorescence and fluorescence enhancement is promoted by deprotonating the sensor's amide. One of the sensors is highly selective for Zn2+ over Cd2+ and other cations such as Hg2+, Fe2+, Mn2+ and Ca2+. This selectivity can be attributed to the increased absorption of the sensor in the presence of Zn2+ and the strong binding of Zn2+. Structural studies, including X-ray and NMR, show the ability of dipicolylamine (DPA) to bind in facial and meridional manners to Zn2+. Crystal structures of different compounds show Zn2+ coordinating to three, four, and five nitrogens from the compounds. They also indicate that the selectivity of DPA containing compounds towards Zn2+ may originate from Zn2+ being stable in different coordination environments. (C) 2012 Elsevier B. V. All rights reserved.