4-chloroacetamido-9-(2-chloroacetoxyethyl)-1,8-naphthalimide | 1022899-79-1

• 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-chloroacetamido-9-(2-chloroacetoxyethyl)-1,8-naphthalimide
• 英文别名: 2-[6-[(2-Chloroacetyl)amino]-1,3-dioxobenzo[de]isoquinolin-2-yl]ethyl 2-chloroacetate
• CAS: 1022899-79-1
• 化学式: C₁₈H₁₄Cl₂N₂O₅
• 分子量: 409.226
• InChiKey: SEMUJBGJKZUTBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloroacetamido-9-(2-chloroacetoxyethyl)-1,8-naphthalimide 、 二甲基吡啶胺 在 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以69%的产率得到
  参考文献：
  名称：

  Pyrophosphate-Selective Fluorescent Chemosensor Based on 1,8-Naphthalimide–DPA–Zn(II) Complex and Its Application for Cell Imaging

  摘要：

  A new zinc(II) complex with a two-dipicolylamine-substituted 1,8-naphthalimide for recognition of pyrophosphate with ratiometrical fluorescence changes in aqueous solution has been synthesized and characterized. Its biological application to monitor the intracellular pyrophosphate (PPi) was successfully demonstrated by the observation that the fluorescence of 1 was enhanced by the presence of the Zn(2+) ion and was quenched by addition of PPi.

  DOI：

  10.1021/ol202159x
• 作为产物：
  描述：

  4-硝基-1,8-萘醛酸酐 在 盐酸 、 4-二甲氨基吡啶 、 tin(II) chloride dihdyrate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 13.5h， 生成 4-chloroacetamido-9-(2-chloroacetoxyethyl)-1,8-naphthalimide
  参考文献：
  名称：

  Pyrophosphate-Selective Fluorescent Chemosensor Based on 1,8-Naphthalimide–DPA–Zn(II) Complex and Its Application for Cell Imaging

  摘要：

  A new zinc(II) complex with a two-dipicolylamine-substituted 1,8-naphthalimide for recognition of pyrophosphate with ratiometrical fluorescence changes in aqueous solution has been synthesized and characterized. Its biological application to monitor the intracellular pyrophosphate (PPi) was successfully demonstrated by the observation that the fluorescence of 1 was enhanced by the presence of the Zn(2+) ion and was quenched by addition of PPi.

  DOI：

  10.1021/ol202159x

文献信息

• The synthesis and fluorescence of novel <i>N</i> ‐substituted‐1,8‐naphthylimides
  作者：Dongwu Yuan、Robert G Brown、John D Hepworth、Michael S Alexiou、John H. P. Tyman

  DOI：10.1002/jhet.5570450216

  日期：2008.3

  Abstractmagnified imageThe synthesis and characterisation of a series of novel 4‐acylamino and 4‐alkylamino‐N‐1,8‐naphthalimides is described. The UV‐visible absorption and emission properties of the compounds are reported. Significant solvent effects are noted for 4‐n‐butyl‐9‐n‐butyl‐1,8‐naphthylimide. The incorporation of acetyl and chloroacetyl groups into the 4‐substituent markedly increases the fluorescence quantum yield compared with 4‐alkylamino substituemnts.
• Pyrophosphate-Selective Fluorescent Chemosensor Based on 1,8-Naphthalimide–DPA–Zn(II) Complex and Its Application for Cell Imaging
  作者：Jun Feng Zhang、Sooyeon Kim、Ji Hae Han、Seung-Jea Lee、Tuhin Pradhan、Qian Yong Cao、Suk Joong Lee、Chulhun Kang、Jong Seung Kim

  DOI：10.1021/ol202159x

  日期：2011.10.7

  A new zinc(II) complex with a two-dipicolylamine-substituted 1,8-naphthalimide for recognition of pyrophosphate with ratiometrical fluorescence changes in aqueous solution has been synthesized and characterized. Its biological application to monitor the intracellular pyrophosphate (PPi) was successfully demonstrated by the observation that the fluorescence of 1 was enhanced by the presence of the Zn(2+) ion and was quenched by addition of PPi.