7-amino-4-(trifluoromethyl)coumarin | 903898-41-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-amino-4-(trifluoromethyl)coumarin
• 英文别名: 7-(2-chloroacetayl)amino-4-(trifluoromethyl)coumarin；2-chloro-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]acetamide
• CAS: 903898-41-9
• 化学式: C₁₂H₇ClF₃NO₃
• 分子量: 305.641
• InChiKey: DSEVIHCLQZSZDK-UHFFFAOYSA-N

物化性质

• 熔点：
  182-185 °C
• 沸点：
  426.8±45.0 °C(Predicted)
• 密度：
  1.586±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-amino-4-(trifluoromethyl)coumarin 在 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成
  参考文献：
  名称：

  Photophysics of Coumarin and Carbostyril-Sensitized Luminescent Lanthanide Complexes: Implications for Complex Design in Multiplex Detection

  摘要：

  Luminescent lanthanide (Ln(III)) complexes with coumarin or carbostyril antennae were synthesized and their photophysical properties evaluated using steady-state and time-resolved UV-vis spectroscopy. Ligands bearing distant hydroxycoumarin-derived antennae attached through triazole linkers were modest sensitizers for Eu(III) and Tb(III), whereas ligands with 7-amidocarbostyrils directly linked to the coordination site could reach good quantum yields for multiple Ln(III), including the visible emitters Sm(III) and Dy(III), and the near-infrared emitters Nd(III) and Yb(III). The highest lanthanide-centered luminescence quantum yields were 35% (Tb), 7.9% (Eu), 0.67% (Dy), and 0.18% (Sm). Antennae providing similar luminescence intensities with 2-4 Ln-emitters were identified. Photoredox quenching of the carbostyril antenna excited states was observed for all Eu(III)-complexes and should be sensitizing in the case of Yb(III); the scope of the process extends to Ln(III) for which it has not been seen previously, specifically Dy(III) and Sm(III). The proposed process is supported by photophysical and electrochemical data. A FRET-type mechanism was identified in architectures with both distant and close antennae for all of the Lns. This mechanism seems to be the only sensitizing one at long distance and probably contributes to the sensitization at shorter distances along with the triplet pathway. The complexes were nontoxic to either bacterial or mammalian cells. Complexes of an ester-functionalized ligand were taken up by bacteria in a concentration-dependent manner. Our results suggest that the effects of FRET and photoredox quenching should be taken into consideration when designing luminescent Ln complexes. These results also establish these Ln(III)-complexes for multiplex detection beyond the available two-color systems.

  DOI：

  10.1021/jacs.6b11274
• 作为产物：
  描述：

  香豆素 151 、 氯乙酰氯 在 N,N-二异丙基乙胺 作用下， 反应 2.0h， 以97%的产率得到7-amino-4-(trifluoromethyl)coumarin
  参考文献：
  名称：

  Coumarin-derived transformable fluorescent sensor for Zn2+

  摘要：

  我们报告了一种香豆素衍生的 Zn2+ 荧光传感器，称为 CTS。由于 CTS 具有可转化能力，即 Zn2+ 可置换其他金属离子，从而诱导螯合作用从酰胺形式转化为酰亚胺酸同分异构形式，因此 CTS 对 Zn2+ 的结合选择性优于其他竞争金属离子。

  DOI：

  10.1039/c2cc30963g

文献信息

• Co(II) Macrocyclic Complexes Appended with Fluorophores as paraCEST and cellCEST Agents
  作者：Akanksha Patel、Samira M. Abozeid、Paul J. Cullen、Janet R. Morrow

  DOI：10.1021/acs.inorgchem.0c02470

  日期：2020.11.16

  Four high-spin macrocyclic Co(II) complexes with hydroxypropyl or amide pendants and appended coumarin or carbostyril fluorophores were prepared as CEST (chemical exchange saturation transfer) MRI probes. The complexes were studied in solution as paramagnetic CEST (paraCEST) agents and after loading into Saccharomyces cerevisiae yeast cells as cell-based CEST (cellCEST) agents. The fluorophores attached

  制备了四个带有羟丙基或酰胺侧基的高自旋大环Co（II）配合物，并附加了香豆素或卡苯乙烯基荧光团作为CEST（化学交换饱和转移）MRI探针。在溶液中以顺磁性CEST（paraCEST）剂以及装入酿酒酵母后对复合物进行了研究酵母细胞作为基于细胞的CEST（cellCEST）试剂。通过酰胺键连接到配合物上的荧光团通过电离归因于酰胺NH连接基团的基团，使所有四个配合物的paraCEST特性具有不同寻常的pH依赖性。当pH从5增加到7.5时，羟丙基基络合物的最远CEST峰变化了〜90 ppm。在酸性pH值下，Co（II）配合物表现出三到四个CEST峰，并且在200 ppm处位移最大的CEST峰。该配合物表现出明显的顺磁性水质子转移，这是开发cellCEST试剂所必需的。质子共振的大位移归因于中性pH下的内层水，如温度变化17所示NMR光谱学研究。用这些paraCEST试剂之一标记酵母，通过荧光显微镜
• Fluoride sensing with a PCT-based calix[4]arene
  作者：Suh Hyun Lee、Hyun Jung Kim、Yeon Ok Lee、Jacques Vicens、Jong Seung Kim

  DOI：10.1016/j.tetlet.2006.04.093

  日期：2006.6

  Novel calix[4]arene-based anion sensor 1 with two coumarin units attached via amido functions acting also as binding sites is presented. Complexation of F- by PCT-based 1 causes selectively red-shift in UV-vis absorption and in fluorescence emission due to H-bonding followed by deprotonation of NH-amide groups. (c) 2006 Elsevier Ltd. All rights reserved.
• Ion-Induced FRET On−Off in Fluorescent Calix[4]arene
  作者：Min Hee Lee、Duong Tuan Quang、Hyo Sung Jung、Juyoung Yoon、Chang-Hee Lee、Jong Seung Kim

  DOI：10.1021/jo070361y

  日期：2007.5.1

  A novel calix[4]arene bearing one 2,3-naphthocrown-6 and two coumarin amide units at the lower rim in partial-cone conformation (1) was synthesized as a colorimetric and FRET-based fluorometric sensor for F- and Cs+ ions. Intramolecular FRET from the naphthalene emission to the coumarin absorption affords high fluorescence selectivity toward F- and Cs+ ions.