tert-butyl [4-(1,10-phenanthrolin-5-yl)phenyl]carbamate | 1334286-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl [4-(1,10-phenanthrolin-5-yl)phenyl]carbamate
• CAS: 1334286-48-4
• 化学式: C₂₃H₂₁N₃O₂
• 分子量: 371.439
• InChiKey: YRDOTGXAXZVXHM-UHFFFAOYSA-N

物化性质

• 沸点：
  502.1±50.0 °C(predicted)
• 密度：
  1.244±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.11
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl [4-(1,10-phenanthrolin-5-yl)phenyl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到4-(1,10-phenanthrolin-5-yl)aniline
  参考文献：
  名称：

  A Heterobimetallic Ruthenium–Gadolinium Complex as a Potential Agent for Bimodal Imaging

  摘要：

  Trinuclear heterobimetallic Ln(III)-Ru-II cornplexes (Ln = Eu, Gd) based on a 1,10-phenanthroline ligand bearing a diethylenetriaminepentaacetic acid (DTPA) core have been synthesized and fully characterized by a range of experimental techniques. The O-17 NMR and proton nuclear magetic relaxation dispersion (NMRD) measurements of Gd-III-Ru-II show that, in comparison to the parent Gd-DTPA, this complex exhibits improved relaxivity, which is the result of an increase of the rotational correlation time. Relaxometry and ultrafiltration experiments indicate that the 1,10-phenanthroline ligand has a high affinity for noncovalent binding to human serum albumin, which results in a high relaxivity r(1) of 14.3 s(-1) mM(-1) at 20 MHz and 37 degrees C. Furthermore, the Ln(III)-Ru-II complexes (Ln = Eu, Gd) show an intense light absorption in the visible spectral region due to metal-to-ligand charge transfer (MLCT) transitions. Upon excitation into the MLCT band at 440 nm, the complexes exhibit a bright-red luminescence centered at 610 nm, with a quantum yield of 4.7%. The luminescence lifetime equals 540 ns and is therefore long enough to exceed the fluorescent background. Monometallic lanthanide complexes have also been synthesized, and the Eu-III analogue shows a characteristic red luminescence with a quantum yield of 0.8%. Taking into account the relaxometric and luminescent properties, the developed Gd-III-Ru-II complex can be considered as a potential in vitro bimodal imaging agent.

  DOI：

  10.1021/ic200726t
• 作为产物：
  描述：

  5-溴-1,10-菲罗啉 、 N-Boc-4-氨基苯硼酸频哪醇酯 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 touene 、 水 为溶剂， 反应 16.0h， 以68%的产率得到tert-butyl [4-(1,10-phenanthrolin-5-yl)phenyl]carbamate
  参考文献：
  名称：

  A Heterobimetallic Ruthenium–Gadolinium Complex as a Potential Agent for Bimodal Imaging

  摘要：

  Trinuclear heterobimetallic Ln(III)-Ru-II cornplexes (Ln = Eu, Gd) based on a 1,10-phenanthroline ligand bearing a diethylenetriaminepentaacetic acid (DTPA) core have been synthesized and fully characterized by a range of experimental techniques. The O-17 NMR and proton nuclear magetic relaxation dispersion (NMRD) measurements of Gd-III-Ru-II show that, in comparison to the parent Gd-DTPA, this complex exhibits improved relaxivity, which is the result of an increase of the rotational correlation time. Relaxometry and ultrafiltration experiments indicate that the 1,10-phenanthroline ligand has a high affinity for noncovalent binding to human serum albumin, which results in a high relaxivity r(1) of 14.3 s(-1) mM(-1) at 20 MHz and 37 degrees C. Furthermore, the Ln(III)-Ru-II complexes (Ln = Eu, Gd) show an intense light absorption in the visible spectral region due to metal-to-ligand charge transfer (MLCT) transitions. Upon excitation into the MLCT band at 440 nm, the complexes exhibit a bright-red luminescence centered at 610 nm, with a quantum yield of 4.7%. The luminescence lifetime equals 540 ns and is therefore long enough to exceed the fluorescent background. Monometallic lanthanide complexes have also been synthesized, and the Eu-III analogue shows a characteristic red luminescence with a quantum yield of 0.8%. Taking into account the relaxometric and luminescent properties, the developed Gd-III-Ru-II complex can be considered as a potential in vitro bimodal imaging agent.

  DOI：

  10.1021/ic200726t