N-[3-([3-(N-(1,8-naphthalimidyl))propyl]methylamino)propyl]-N'-propylurea | 1048014-12-5

• 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: N-[3-([3-(N-(1,8-naphthalimidyl))propyl]methylamino)propyl]-N'-propylurea
• 英文别名: 1-[3-[3-(1,3-Dioxobenzo[de]isoquinolin-2-yl)propyl-methylamino]propyl]-3-propylurea；1-[3-[3-(1,3-dioxobenzo[de]isoquinolin-2-yl)propyl-methylamino]propyl]-3-propylurea
• CAS: 1048014-12-5
• 化学式: C₂₃H₃₀N₄O₃
• 分子量: 410.516
• InChiKey: UTXKAIPMWFJPJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异氰酸丙酯 、 N-[3-[(3-aminopropyl)methylamino]propyl]-1,8-naphthalimide 反应 0.08h， 以79%的产率得到N-[3-([3-(N-(1,8-naphthalimidyl))propyl]methylamino)propyl]-N'-propylurea
  参考文献：
  名称：

  Modular Functional Integration of a Two-Input INH Logic Gate with a Fluorophore−Spacer−Receptor₁−Spacer−Receptor₂ Conjugate

  摘要：

  The synthesis and photophysical characterization of a fluorophore-spacer-receptor(1)spacer-receptor(2) system, which combines the 1,8-naphthalimide fluorophore with amine and urea receptor units, is reported. Photoinduced electron transfer (PET) from the amino group was blocked by protonation, leading to a drastic fluorescence enhancement (ca. 20 times). Interaction of the urea receptor with anions (F-, AcO-, H2PO4-) via hydrogen bonding or urea NH deprotonation resulted in significant fluorescence quenching of the 1,8-naphthalimide chromophore in an appropriately chosen model compound (ca. 30-45%). In the presence of both chemical input species, protons and anions, the fluorescence was also quenched. The binding of the anions by NH+ ammonium receptor has been assumed. The apparent anion binding constants of the protonated conjugate follow the basicity trend of the anions: AcO- similar to F- > H2PO4-. The investigated system constitutes an example for the flexible and modular realization of functionally integrated INH logic at the molecular level, using protons and anions as chemical input species and the fluorescence of a PET-active signaling unit as output.

  DOI：

  10.1021/jo800342t