4-(2-(4-(cyano)phenyl)ethynyl)-1,8-naphthalic anhydride | 1276688-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2-(4-(cyano)phenyl)ethynyl)-1,8-naphthalic anhydride
• 英文别名: 4-[2-(2,4-Dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-8-yl)ethynyl]benzonitrile
• CAS: 1276688-43-7
• 化学式: C₂₁H₉NO₃
• 分子量: 323.307
• InChiKey: VUNOOUFUKBNVJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-(4-(cyano)phenyl)ethynyl)-1,8-naphthalic anhydride 、 炔丙胺 以 乙醇 为溶剂， 以67%的产率得到4-(4-cyanophenylethynyl)-N-(2-propynyl)-1,8-naphthalimide
  参考文献：
  名称：

  Highly solvatochromic fluorescent naphthalimides: Design, synthesis, photophysical properties and fluorescence switch-on sensing of ct-DNA

  摘要：

  We report the design, synthesis and photophysical properties of highly solvatochromic donor/acceptor substituted naphthalimide based fluorophores. The synthesized naphthalimides containing propargyl ends showed highly solvatochromic intramolecular charge transfer (ICT) feature as was revealed from the UV-visible, fluorescence photophysical properties of these fluorophores and DFT/TDDFT calculation. Fluorescence life times for the imide fluorophores were also measured in different solvents. The solid state photophysical property of donor substituted naphthalimide 1 showed promising for future application in material sciences. Furthermore, both the donor/acceptor substituted naphthalimide fluorophores 1-2 were exploited in sensing calf-thymus DNA via switch-on fluorescence response. The propargyl linker containing naphthalimides can further be exploited for the synthesis of labeled biomolecular building blocks. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.003
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 、 4-乙炔基苯甲腈 在 四(三苯基膦)钯 、 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以65%的产率得到4-(2-(4-(cyano)phenyl)ethynyl)-1,8-naphthalic anhydride
  参考文献：
  名称：

  Click-Reagent Version of Sonogashira Coupling Protocol to Conjugated Fluorescent Alkynes with No or Reduced Homocoupling

  摘要：

  A click-reagent version of the Sonogashira-coupling protocol has been developed. Diarylalkynes with donor and/or acceptor substituents have been synthesized via this protocol at moderate to excellent yields and with no or drastically reduced quantities of undesired homocoupled side products. This protocol is green-solvent compatible, air-insensitive, and effective under microwave conditions.

  DOI：

  10.1021/jo200005n

文献信息

• Click-Reagent Version of Sonogashira Coupling Protocol to Conjugated Fluorescent Alkynes with No or Reduced Homocoupling
  作者：Subhendu Sekhar Bag、Rajen Kundu、Manas Das

  DOI：10.1021/jo200005n

  日期：2011.4.1

  A click-reagent version of the Sonogashira-coupling protocol has been developed. Diarylalkynes with donor and/or acceptor substituents have been synthesized via this protocol at moderate to excellent yields and with no or drastically reduced quantities of undesired homocoupled side products. This protocol is green-solvent compatible, air-insensitive, and effective under microwave conditions.
• Highly solvatochromic fluorescent naphthalimides: Design, synthesis, photophysical properties and fluorescence switch-on sensing of ct-DNA
  作者：Subhendu Sekhar Bag、Manoj Kumar Pradhan、Rajen Kundu、Subhashis Jana

  DOI：10.1016/j.bmcl.2012.11.003

  日期：2013.1

  We report the design, synthesis and photophysical properties of highly solvatochromic donor/acceptor substituted naphthalimide based fluorophores. The synthesized naphthalimides containing propargyl ends showed highly solvatochromic intramolecular charge transfer (ICT) feature as was revealed from the UV-visible, fluorescence photophysical properties of these fluorophores and DFT/TDDFT calculation. Fluorescence life times for the imide fluorophores were also measured in different solvents. The solid state photophysical property of donor substituted naphthalimide 1 showed promising for future application in material sciences. Furthermore, both the donor/acceptor substituted naphthalimide fluorophores 1-2 were exploited in sensing calf-thymus DNA via switch-on fluorescence response. The propargyl linker containing naphthalimides can further be exploited for the synthesis of labeled biomolecular building blocks. (C) 2012 Elsevier Ltd. All rights reserved.