N-(3-dimethylaminopropyl)-3-chloro-1,8-naphthalimide | 69408-94-2

• 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-dimethylaminopropyl)-3-chloro-1,8-naphthalimide
• 英文别名: 5-Chloro-2-[3-(dimethylamino)propyl]benzo[de]isoquinoline-1,3-dione
• CAS: 69408-94-2
• 化学式: C₁₇H₁₇ClN₂O₂
• 分子量: 316.787
• InChiKey: XWVLLKKFXOPVLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-(3-dimethylaminopropyl)-3-chloro-1,8-naphthalimide 在 sodium methylate 作用下， 反应 6.0h， 生成 2-(3-Dimethylamino-propyl)-5-methoxy-benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Unusually High Fluorescence Enhancement of Some 1,8-Naphthalimide Derivatives Induced by Transition Metal Salts

  摘要：

  Three-component systems, 1a-c and 2a,b, comprising 1,8-naphthalimide and 4-methoxy-1,8-naphthalimide as fluorophore, a dimethylamino moiety as guest binding site and a polymethylene group as spacer, have been synthesized and the fluorescence behavior of these systems has been studied in the absence and in the presence of the salts of several transition metal ions. The systems an found to be very weakly fluorescent compared to their constituent fluorophores (3 and 4) and this observation has been ascribed to photoinduced intramolecular electron transfer (PIET) between the electron rich amino moiety (donor) and relatively electron deficient fluorophore component (acceptor). Spectral and electrochemical data indicate the thermodynamic feasibility of PIET (exergonic free energy changes) in these multicomponent systems and PIET is found to be most efficient in systems where the fluorophore and the amino moiety are separated by two methylene groups. Fluorescence decay behavior of the systems suggest that PIET occurs by a through-space mechanism. In the presence of the transition metal ions, well-known for their fluorescence quenching abilities, the present systems exhibit significant fluorescence enhancement (FE). Moreover, it has been observed that guest-induced FE can even be severalfold higher than that expected from consideration of PIET in the system. It is suggested that a system can exhibit unusually high FE when the guest is capable of inducing FE by more than one means, in the present case, it is shown that preferential solvation of the fluorophore by the water molecules of the hydrated metal salts could be partially responsible for the high FE values.

  DOI：

  10.1021/jp000333i
• 作为产物：
  描述：

  3-硝基-1,8-萘二甲酸酐 在 五氯化磷 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N-(3-dimethylaminopropyl)-3-chloro-1,8-naphthalimide
  参考文献：
  名称：

  Fernandez Brana; Martinez Sanz; Castellano, European Journal of Medicinal Chemistry, 1981, vol. 16, # 3, p. 207 - 212

  摘要：

  DOI：

文献信息

• N(Aminoalkyl)-naphthalimides and their derivatives
  申请人：Laboratorios Made, S.A.

  公开号：US04204063A1

  公开（公告）日：1980-05-20

  N-substituted-3-substituted naphthalimides are prepared by reacting 3-substituted naphthalic acid with a compound having a primary amino group. The naphthalimides possess cytotoxic properties.

  N-取代-3-取代萘酰亚胺是通过将3-取代萘甲酸与具有一次氨基的化合物反应制备的。这些萘酰亚胺具有细胞毒性。
• BRANA M. F.; SANZ A. M.; CASTELLANO J. M.; ROLDAN C. M.; ROLDAN C., EUR. J. MED. CHEM.-CHIM. THER., 1981, 16, NO 3, 207-212,
  作者：BRANA M. F.、 SANZ A. M.、 CASTELLANO J. M.、 ROLDAN C. M.、 ROLDAN C.

  DOI：——

  日期：——
• US4204063A
  申请人：——

  公开号：US4204063A

  公开（公告）日：1980-05-20
• Fernandez Brana; Martinez Sanz; Castellano, European Journal of Medicinal Chemistry, 1981, vol. 16, # 3, p. 207 - 212
  作者：Fernandez Brana、Martinez Sanz、Castellano、et al.

  DOI：——

  日期：——
• Unusually High Fluorescence Enhancement of Some 1,8-Naphthalimide Derivatives Induced by Transition Metal Salts
  作者：B. Ramachandram、G. Saroja、B. Sankaran、A. Samanta

  DOI：10.1021/jp000333i

  日期：2000.12.1

  Three-component systems, 1a-c and 2a,b, comprising 1,8-naphthalimide and 4-methoxy-1,8-naphthalimide as fluorophore, a dimethylamino moiety as guest binding site and a polymethylene group as spacer, have been synthesized and the fluorescence behavior of these systems has been studied in the absence and in the presence of the salts of several transition metal ions. The systems an found to be very weakly fluorescent compared to their constituent fluorophores (3 and 4) and this observation has been ascribed to photoinduced intramolecular electron transfer (PIET) between the electron rich amino moiety (donor) and relatively electron deficient fluorophore component (acceptor). Spectral and electrochemical data indicate the thermodynamic feasibility of PIET (exergonic free energy changes) in these multicomponent systems and PIET is found to be most efficient in systems where the fluorophore and the amino moiety are separated by two methylene groups. Fluorescence decay behavior of the systems suggest that PIET occurs by a through-space mechanism. In the presence of the transition metal ions, well-known for their fluorescence quenching abilities, the present systems exhibit significant fluorescence enhancement (FE). Moreover, it has been observed that guest-induced FE can even be severalfold higher than that expected from consideration of PIET in the system. It is suggested that a system can exhibit unusually high FE when the guest is capable of inducing FE by more than one means, in the present case, it is shown that preferential solvation of the fluorophore by the water molecules of the hydrated metal salts could be partially responsible for the high FE values.