7-[N-(p-toluenesulfonyl)amino]-4-trifluoromethylcoumarin | 427880-47-5

• 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-[N-(p-toluenesulfonyl)amino]-4-trifluoromethylcoumarin
• 英文别名: 7-tosylamino-4-trifluoromethylcoumarin；4-methyl-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]benzenesulfonamide
• CAS: 427880-47-5
• 化学式: C₁₇H₁₂F₃NO₄S
• 分子量: 383.348
• InChiKey: QNEXCXSFYXYEFF-UHFFFAOYSA-N

物化性质

• 熔点：
  193-194 °C
• 沸点：
  475.3±55.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-[N-(p-toluenesulfonyl)amino]-4-trifluoromethylcoumarin 在 硫酸 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 38.0h， 生成 7-[2-(1,4,7,10-tetraazacyclododecan-1-yl)ethylamino]-4-trifluoromethylcoumarin
  参考文献：
  名称：

  A Fluorescent Anion Sensor That Works in Neutral Aqueous Solution for Bioanalytical Application

  摘要：

  Anion recognition and anion sensing are of interest because anions play many important roles in living organisms. Most currently known anion sensors work only in organic solution, but sensors for biological applications are required to function in neutral aqueous solution. We have designed and synthesized a novel fluorescent sensor for anions. The sensor molecule 11-Cd-II contains 7-amino-4-trifluoromethylcoumarin as a fluorescent reporter and Cd-II-cyclen (1,4,7,10-tetraazacyclododecane) as an anion host. In neutral aqueous solution, Cd-II of 1-Cd-II is coordinated by the four nitrogen atoms of cyclen and the aromatic amino group of coumarin. When various anions are added to 100 mM HEPES buffer solution (pH 7.4) containing 1-Cd-II, the aromatic amino group of coumarin is displaced from Cd-II, causing a change of the excitation spectrum. While pyrophosphate and citrate were detected with high sensitivity, fluoride and perchlorate produced no response. Among organic anions, ATP and ADP gave strong signals, while CAMP showed little signal. By utilizing the different affinities of the sensor for AMP and cAMP, the activity of phosphodiesterase, which cleaves cyclic nucleotide, was monitored in real-time. The sensor should have many biochemical and analytical applications and the sensing principle should be widely applicable to the sensing of other molecules.

  DOI：

  10.1021/ja0175643
• 作为产物：
  描述：

  香豆素 151 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以91%的产率得到7-[N-(p-toluenesulfonyl)amino]-4-trifluoromethylcoumarin
  参考文献：
  名称：

  Coumarin-based novel fluorescent zinc ion probe in aqueous solution

  摘要：

  A novel coumarin-derived fluorescent probe, FCP, was designed for Zn2+ quantification based on the photo-induced electron transfer (PET) mechanism. This probe selectively and sensitively detects Zn2+ in aqueous solution with wide pH range. Large fluorescence enhancement (13-fold) was observed upon the addition of Zn2+. FCP also displays excellent cell permeability in HeLa cell model and very low cytotoxicity to HEK-293 cell model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.032

文献信息

• A Fluorescent Anion Sensor That Works in Neutral Aqueous Solution for Bioanalytical Application
  作者：Shin Mizukami、Tetsuo Nagano、Yasuteru Urano、Akira Odani、Kazuya Kikuchi

  DOI：10.1021/ja0175643

  日期：2002.4.1

  Anion recognition and anion sensing are of interest because anions play many important roles in living organisms. Most currently known anion sensors work only in organic solution, but sensors for biological applications are required to function in neutral aqueous solution. We have designed and synthesized a novel fluorescent sensor for anions. The sensor molecule 11-Cd-II contains 7-amino-4-trifluoromethylcoumarin as a fluorescent reporter and Cd-II-cyclen (1,4,7,10-tetraazacyclododecane) as an anion host. In neutral aqueous solution, Cd-II of 1-Cd-II is coordinated by the four nitrogen atoms of cyclen and the aromatic amino group of coumarin. When various anions are added to 100 mM HEPES buffer solution (pH 7.4) containing 1-Cd-II, the aromatic amino group of coumarin is displaced from Cd-II, causing a change of the excitation spectrum. While pyrophosphate and citrate were detected with high sensitivity, fluoride and perchlorate produced no response. Among organic anions, ATP and ADP gave strong signals, while CAMP showed little signal. By utilizing the different affinities of the sensor for AMP and cAMP, the activity of phosphodiesterase, which cleaves cyclic nucleotide, was monitored in real-time. The sensor should have many biochemical and analytical applications and the sensing principle should be widely applicable to the sensing of other molecules.
• Coumarin-based novel fluorescent zinc ion probe in aqueous solution
  作者：Jun Li、Chun-Fang Zhang、Ze-Zhong Ming、Ge-Fei Hao、Wen-Chao Yang、Guang-Fu Yang

  DOI：10.1016/j.tet.2013.03.032

  日期：2013.6

  A novel coumarin-derived fluorescent probe, FCP, was designed for Zn2+ quantification based on the photo-induced electron transfer (PET) mechanism. This probe selectively and sensitively detects Zn2+ in aqueous solution with wide pH range. Large fluorescence enhancement (13-fold) was observed upon the addition of Zn2+. FCP also displays excellent cell permeability in HeLa cell model and very low cytotoxicity to HEK-293 cell model. (C) 2013 Elsevier Ltd. All rights reserved.