2-(2-(2-ethoxyethoxy)ethoxy)isoindoline-1,3-dione | 54149-24-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2-(2-ethoxyethoxy)ethoxy)isoindoline-1,3-dione
• 英文别名: N-[2-(2-ethoxy-ethoxy)-ethoxy]-phthalimide；2-[2-(2-Ethoxyethoxy)ethoxy]isoindole-1,3-dione
• CAS: 54149-24-5
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: VFBNYXJBOIRUKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-(2-ethoxyethoxy)ethoxy)isoindoline-1,3-dione 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 以78 %的产率得到2-(2-(2-乙氧基乙氧基)乙氧基)乙胺
  参考文献：
  名称：

  Design and synthesis of fluorescent BODIPY derivatives with D-A structure for cancer cell imaging

  摘要：

  Boron-dipyrromethene (BODIPY) as a traditional fluorescent dye has received increasing attention because of its high molar extinction coefficient, easy modification, and good light stability. In this work, three BODIPY compounds (BDP-1, BDP-2 and BDP-3) were designed and synthesized by introducing PEG chains and a naphthalimide (NI) group onto the parent structure of BODIPY. Due to the electron-withdrawing properties of NI, the compounds of BDP-2 and BDP-3 formed a typical donor (D)-acceptor (A) structure, which led to the red-shifted absorption and fluorescence spectrum. The synthesized BODIPY exhibited intense green emission, with fluorescence quantum yield of 0.66, 0.29, and 0.19 for BDP-1, BDP-2 and BDP-3 respectively. The decrease in fluorescence of BDP-2 and BDP-3 was probably ascribed to the enhanced intramolecular charge transfer because of the introduction of the NI group. The good biocompatibility and low cytotoxicity of the synthesized BODIPY compounds were verified by the CCK-8 assay. The subcellular localization of the three compounds was further evaluated through a confocal laser scanning microscope. The results showed that these BODIPY derivatives were mainly localized in the lysosomes of cancer cells. Thus, the synthesized BODIPY fluorescent dyes show promising applications in tumor imaging benefiting from their good biocompatibility and strong fluorescence.

  DOI：

  10.1142/s1088424624500391
• 作为产物：
  描述：

  二乙二醇乙醚 在 吡啶 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 2-(2-(2-ethoxyethoxy)ethoxy)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthèse et activité biologique de prodrogues de l'acide oxolinique

  摘要：

  Antiseptic phenols, anti-inflammatory acids and polyethyleneglycol moieties have been attached by labile bonds to oxolinic acid giving pro-drugs with anti-bacterial activities. Some of them are more soluble in water, exhibit a more sustained action in the time and give higher plasma and tissue concentrations compared with the free drug.

  DOI：

  10.1016/0223-5234(91)90108-y