4-(2-aminoethylamino)-N-(ethyl)-1,8-naphthalimide | 864950-15-2

• 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: 4-(2-aminoethylamino)-N-(ethyl)-1,8-naphthalimide
• 英文别名: 6-(2-Aminoethylamino)-2-ethylbenzo[de]isoquinoline-1,3-dione；6-(2-aminoethylamino)-2-ethylbenzo[de]isoquinoline-1,3-dione
• CAS: 864950-15-2
• 化学式: C₁₆H₁₇N₃O₂
• 分子量: 283.33
• InChiKey: HAQQJFWKDZKZBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-aminoethylamino)-N-(ethyl)-1,8-naphthalimide 、 4-三氟甲基苯基异氰酸酯 以 氯仿 为溶剂， 反应 16.0h， 以66%的产率得到2-ethyl-6-[(4-trifluoromethylphenylcarbamoyl)ethylamino]-benzo[de]iso-quinoline-1,3-dione
  参考文献：
  名称：

  Selective fluorescent PET sensing of fluoride (F−) using naphthalimide–thiourea and –urea conjugates

  摘要：

  The thiourea and urea functionalised 4-amino-1,8-naphthalimide sensors 1-3, based on the. uorophore-spacer-receptor principle, were synthesised in high yield in three steps. The sensors were shown to signal selectively the detection of fluoride in the fluorescence emission spectrum in DMSO. On all occasions the emission was quenched due to enhanced photoinduced electron transfer quenching (PET) from the receptor to the excited state of the fluorophore upon recognition of F-, particularly for the thiourea sensors 1 and 2. In comparison, the changes in the absorption spectra were minor for all three, even after the addition of 80-100 equiv of F-. The sensing of acetate or dihydrogenphosphate gave rise to only similar to 5-20% quenching. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.026
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 以 甲苯 为溶剂， 反应 12.0h， 生成 4-(2-aminoethylamino)-N-(ethyl)-1,8-naphthalimide
  参考文献：
  名称：

  4-Amino-1,8-naphthalimide-based anion receptors: employing the naphthalimide N–H moiety in the cooperative binding of dihydrogenphosphate

  摘要：

  The 4-amino-1,8-naplitlialimide-based anion receptor 3 binds dihydrogenphosphate with 1:1 stoichiometry through cooperative hydrogen bonding to a naplithalimide N-H and thiourea N-H groups. This was clearly established from H-1 NMR titration experiments in DMSO-d(6) where a Substantial shift in the resonance for the naphthalimide N-H was observed concomitant with the expected thiourea N-H chemical shift migration upon successive additions of H2PO4-. However, whilst H-1 NMR titration experiments indicate that 3 was capable of binding other anions such as acetate, the naphthalimide N-H does not participate and the N-H resonance was essentially invariant during the titration. The lack of cooperative binding in this instance was justifiable on steric grounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.067

文献信息

• Synthesis and fluorescence sensing properties of a new naphthalimide derivative of calix[4]arene
  作者：Ozlem Sahin、Mustafa Yilmaz

  DOI：10.1016/j.tetlet.2012.02.104

  日期：2012.5

  naphthalimide derivative of calix[4]arene was synthesized as a highly selective fluorescent compound for Cu2+ among the selected metal ions. This compound was examined for its fluorescent properties toward different metal ions (Na+, Li+, Mg2+, Ni2+, Ba2+, Ca2+, Cu2+, Pb2+, Zn2+) and anions (F−, Cl−, Br−, H2PO4-, NO3-, I−, HSO4-, CH3COO−) by UV, NMR and fluorescence spectroscopy.

  合成了杯[4]芳烃的一种新的萘二甲酰亚胺衍生物，作为对所选金属离子中Cu 2+的高选择性荧光化合物。研究了该化合物对不同金属离子（Na +，Li +，Mg 2 +，Ni 2 +，Ba 2 +，Ca 2 +，Cu 2 +，Pb 2 +，Zn 2+）和阴离子（荧光）的荧光性质。˚F - ，氯- ，溴- ，H2个采购订单4--， 不3--，我-，HSO4--，CH 3 COO - ）通过UV，NMR和荧光光谱。
• A luminescent pH-sensitive lysosome targeting Eu(<scp>iii</scp>) probe
  作者：Kritika Gupta、Madhu Verma、Priyanka Srivastava、Sri Sivakumar、Ashis K. Patra

  DOI：10.1039/c9nj05561d

  日期：——

  A pH-responsive, water soluble luminescent Eu(iii) probe is designed to target lysosomes via intrinsic f–f emission from the Eu(iii) centre.

  设计了一种pH响应性、水溶性的荧光Eu（III）探针，通过Eu（III）中心的固有f-f发射来靶向溶酶体。
• 4-Amino-1,8-naphthalimide-based anion receptors: employing the naphthalimide N–H moiety in the cooperative binding of dihydrogenphosphate
  作者：Frederick M. Pfeffer、Alisha M. Buschgens、Neil W. Barnett、Thorfinnur Gunnlaugsson、Paul E. Kruger

  DOI：10.1016/j.tetlet.2005.07.067

  日期：2005.9

  The 4-amino-1,8-naplitlialimide-based anion receptor 3 binds dihydrogenphosphate with 1:1 stoichiometry through cooperative hydrogen bonding to a naplithalimide N-H and thiourea N-H groups. This was clearly established from H-1 NMR titration experiments in DMSO-d(6) where a Substantial shift in the resonance for the naphthalimide N-H was observed concomitant with the expected thiourea N-H chemical shift migration upon successive additions of H2PO4-. However, whilst H-1 NMR titration experiments indicate that 3 was capable of binding other anions such as acetate, the naphthalimide N-H does not participate and the N-H resonance was essentially invariant during the titration. The lack of cooperative binding in this instance was justifiable on steric grounds. (c) 2005 Elsevier Ltd. All rights reserved.
• Selective fluorescent PET sensing of fluoride (F−) using naphthalimide–thiourea and –urea conjugates
  作者：Rebecca M. Duke、Thorfinnur Gunnlaugsson

  DOI：10.1016/j.tetlet.2007.09.026

  日期：2007.11

  The thiourea and urea functionalised 4-amino-1,8-naphthalimide sensors 1-3, based on the. uorophore-spacer-receptor principle, were synthesised in high yield in three steps. The sensors were shown to signal selectively the detection of fluoride in the fluorescence emission spectrum in DMSO. On all occasions the emission was quenched due to enhanced photoinduced electron transfer quenching (PET) from the receptor to the excited state of the fluorophore upon recognition of F-, particularly for the thiourea sensors 1 and 2. In comparison, the changes in the absorption spectra were minor for all three, even after the addition of 80-100 equiv of F-. The sensing of acetate or dihydrogenphosphate gave rise to only similar to 5-20% quenching. (C) 2007 Elsevier Ltd. All rights reserved.