4-diethylamino-N-butyl-1,8-naphthalic imide | 75852-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-diethylamino-N-butyl-1,8-naphthalic imide
• 英文别名: 2-Butyl-6-(diethylamino)benzo[de]isoquinoline-1,3-dione
• CAS: 75852-94-7
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: OELWDUZZUQCFRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 aluminum oxide 、 potassium fluoride 、 copper(l) iodide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成 4-diethylamino-N-butyl-1,8-naphthalic imide
  参考文献：
  名称：

  在水性介质中通过铜催化的C–N，C–O和C–S交叉偶联反应轻松获得官能化萘二甲酰亚胺染料的途径

  摘要：

  描述了一种温和，简便，有效的合成方法，该方法通过使用胺，醇和硫醇的CuI催化的C N，C O和C S Ullman型缩合反应合成荧光萘二甲酰亚胺染料。反应在作为绿色溶剂的水中作为温和碱性载体的KF / Al 2 O 3的存在下进行。该方案可耐受各种官能团，并能以良好至极佳的产率提供官能化的萘二甲酰亚胺染料。

  DOI：

  10.1016/j.tetlet.2013.07.010

文献信息

• Nucleophilic displacement of the nitro group in 2- and 4-nitronaphthalic-1, 8-anhydrides and their derivatives
  作者：Michael Alexiou、John Tyman、Ian Wilson

  DOI：10.1016/s0040-4039(01)92917-x

  日期：——

  The nitro group in 2- and 4-nitronaphthalic-1,8-anhydrides can be substituted by amines in certain cases with retention of the anhydride grouping.

  在某些情况下，在保留酸酐基团的情况下，2-和4-硝基萘-1,8-酸酐中的硝基可以被胺取代。
• Microwave-assisted solvent-free synthesis of fluorescent naphthalimide dyes
  作者：Ghasem R. Bardajee

  DOI：10.1016/j.dyepig.2013.04.004

  日期：2013.10

  A series of fluorescent naphthalimide dyes were synthesized via aromatic nucleophilic substitution reaction of 4-bromo-N-alkylnaphthalimides with amines, alkoxides and thiols under microwave irradiation. In this procedure an efficient method for C-N, C-O and C-S bond formation via applying appropriate nucleophiles in the presence of KF/Al2O3 under solvent-free conditions is described. Adducts are produced in good to excellent yields and relatively in short times. The optical properties of three dyes as representative derivatives were examined by UV absorption and steady state fluorescence spectroscopy in solvents with different polarity. (C) 2013 Elsevier Ltd. All rights reserved.
• Influence of the Structure of the Amino Group and Polarity of the Medium on the Photophysical Behavior of 4-Amino-1,8-naphthalimide Derivatives
  作者：Satyen Saha、Anunay Samanta

  DOI：10.1021/jp013287a

  日期：2002.5.1

  Photophysical behavior of two series of 4-amino-1,8-naphthalimide derivatives differing in the amino functionality has been studied as a function of the polarity of the medium. The location of the lowest singlet state of the systems, intramolecular charge transfer (ICT) in nature, is largely controlled by the conformation of the 4-amino group rather than its electron-donating ability. The fluorescence properties of the systems are strongly dependent on the nature of the amino group as well as on the polarity of the media. An increase in the length of the dialkyl groups connected to the amino nitrogen or an increase in the size of the ring containing the amino nitrogen enhances the nonradiative deactivation of the fluorescent state of the molecule. The nonradiative relaxation process is facilitated by an increase in the polarity of the media. The present results suggest that the radiationless deactivation of the fluorescent state of the systems is dependent on the nitrogen inversion rate at the amino group.
• Alexiou, Michael S.; Tyman, John H. P., Journal of Chemical Research, Miniprint, 2000, # 5, p. 632 - 652
  作者：Alexiou, Michael S.、Tyman, John H. P.

  DOI：——

  日期：——
• ALEXIOU M.; TYMAN J.; WILSON I., TETRAHEDRON LETT., 1981, 22, NO 24, 2303-2306
  作者：ALEXIOU M.、 TYMAN J.、 WILSON I.

  DOI：——

  日期：——