4-(N-methylpiperazinyl)-N-(2-aminoethyl)-1,8-naphthalimide | 1220167-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(N-methylpiperazinyl)-N-(2-aminoethyl)-1,8-naphthalimide
• CAS: 1220167-16-7
• 化学式: C₁₉H₂₂N₄O₂
• 分子量: 338.409
• InChiKey: FKWQSBBKQCZCON-UHFFFAOYSA-N

物化性质

• 沸点：
  564.1±50.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  69.88
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(N-methylpiperazinyl)-N-(2-aminoethyl)-1,8-naphthalimide 、 丙烯酸甲酯（MA） 以 甲醇 为溶剂， 反应 72.0h， 以90%的产率得到dimethyl 3,3'-((2-(6-(4-methylpiperazin-1-yl)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)azanediyl)dipropionate
  参考文献：
  名称：

  The design and synthesis of a novel 1,8-naphthalimide PAMAM light-harvesting dendron with fluorescence “off-on” switching core

  摘要：

  A novel polyamidoamine dendron core, peripherally functionalized with 1,8-naphthalimide fluorophores, was configured as a light harvesting antenna in which the system surface was labelled with blue emitting 4-allyloxy-1,8-tiaphtlialimide "donor" dyes capable of both absorbing light and efficiently (96%) transferring the energy to a single, yellow-green emitting 4-N-methylpiperazinyl-1,8-naphthalimide "acceptor" dye. The 1,8-naphthalimide core was designed on the "fluorophore-spacer-receptor" format and was able to function as a fluorescence photoinduced electron transfer sensor. Two different photoinduced electron transfer effects were observed in the new antenna namely that from the receptor to the core fluorophore and that from the polyamidoamine backbone to the peripheral 1,8-naphthalimides. Althogh the core emission intensity of the system was enhanced > four times by reducing the pH from 10 to 2, the fluorescence enhancement of the system in acidic medium, excited within the periphery (lambda(ex) = 360 nm), was approximately twice that of the core fluorescence enhancement after direct excitation of the focal 1,8-naphthalimide (lambda(ex) = 420 nm), because of more efficient energy transfer. The observed "off-on" switching of the core fluorescence over a wid pH scale indicates that the novel light harvesting antenna would be able to act as a highly efficient fluorescent sensor. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2009.09.013
• 作为产物：
  描述：

  N-甲基哌嗪 、 2-(2-aminoethyl)-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 copper(ll) sulfate pentahydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以47%的产率得到4-(N-methylpiperazinyl)-N-(2-aminoethyl)-1,8-naphthalimide
  参考文献：
  名称：

  The design and synthesis of a novel 1,8-naphthalimide PAMAM light-harvesting dendron with fluorescence “off-on” switching core

  摘要：

  A novel polyamidoamine dendron core, peripherally functionalized with 1,8-naphthalimide fluorophores, was configured as a light harvesting antenna in which the system surface was labelled with blue emitting 4-allyloxy-1,8-tiaphtlialimide "donor" dyes capable of both absorbing light and efficiently (96%) transferring the energy to a single, yellow-green emitting 4-N-methylpiperazinyl-1,8-naphthalimide "acceptor" dye. The 1,8-naphthalimide core was designed on the "fluorophore-spacer-receptor" format and was able to function as a fluorescence photoinduced electron transfer sensor. Two different photoinduced electron transfer effects were observed in the new antenna namely that from the receptor to the core fluorophore and that from the polyamidoamine backbone to the peripheral 1,8-naphthalimides. Althogh the core emission intensity of the system was enhanced > four times by reducing the pH from 10 to 2, the fluorescence enhancement of the system in acidic medium, excited within the periphery (lambda(ex) = 360 nm), was approximately twice that of the core fluorescence enhancement after direct excitation of the focal 1,8-naphthalimide (lambda(ex) = 420 nm), because of more efficient energy transfer. The observed "off-on" switching of the core fluorescence over a wid pH scale indicates that the novel light harvesting antenna would be able to act as a highly efficient fluorescent sensor. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2009.09.013