3'-(trifluoromethanesulfonyl)fluorescein | 1398063-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3'-(trifluoromethanesulfonyl)fluorescein
• 英文别名: fluorescein monotrifluoromethanesulfonate；2-[3-oxo-6-(trifluoromethylsulfonyloxy)xanthen-9-yl]benzoic acid
• CAS: 1398063-62-1
• 化学式: C₂₁H₁₁F₃O₇S
• 分子量: 464.375
• InChiKey: AUDRPNPAGQGPKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  663.2±55.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-(trifluoromethanesulfonyl)fluorescein 、 4-氯苯硼酸 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以65%的产率得到2-(3-(4-chlorophenyl)-6-oxo-6H-xanthen-9-yl)benzoic acid
  参考文献：
  名称：

  A highly sensitive fluorescent viscosity sensor

  摘要：

  Variation at the 3' position of fluorescein via Suzuki-Miyaura cross-coupling with aryl and heteroaryl moieties gave a family of anthofluoresceins whose spectroscopic properties were studied. The 1-methylindole derivative gave the highest quantum yield and was observed to behave as a molecular rotor, displaying marked variations in fluorescent intensities with viscosity and offering possible application in cellular sensing and fluorescent polarisation assays. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.101
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 fluorescein free acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以61%的产率得到3'-(trifluoromethanesulfonyl)fluorescein
  参考文献：
  名称：

  A fluorescein-derived anthocyanidin-inspired pH sensor

  摘要：

  A new multicolor pH-dependent fluorophore was synthesized via Pd-mediated cross-coupling chemistry of the mono-triflate of fluorescein with p-hydroxyphenylboronic acid. The novel indicator, named anthofluorescein, is highly sensitive to pH changes between 7 and 10 and displays a green to red fluorescence shift, making it a Valuable candidate for biological studies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.223

文献信息

• Water-Soluble Palladium Reagents for Cysteine <i>S</i>-Arylation under Ambient Aqueous Conditions
  作者：Anthony J. Rojas、Bradley L. Pentelute、Stephen L. Buchwald

  DOI：10.1021/acs.orglett.7b01911

  日期：2017.8.18

  chemoselective modification of cysteine containing proteins and peptides with palladium reagents in aqueous medium. The use of sSPhos allowed for the isolation of several air-stable and water-soluble mono- and bis-palladium reagents, which were used in an improved protocol for the rapid S-arylation of cysteines under benign and physiologically relevant conditions. The cosolvent-free aqueous conditions

  我们报告了使用磺化联芳基膦配体（sSPhos）来促进含钯试剂在水性介质中的半胱氨酸蛋白质和肽的化学选择性修饰。使用sSPhos的允许几个空气稳定的和水溶性的单-和双-钯试剂的分离，这是在一种改进的协议用于快速小号良性和生理相关的条件下半胱氨酸-arylation。无助溶剂的水性条件适用于各种具有亲和标签，杂环，荧光团和功能手柄的生物分子的缀合。另外，使用双钯试剂对带有两个半胱氨酸残基的肽进行大环化。
• A highly sensitive fluorescent viscosity sensor
  作者：Rahimi M. Yusop、Asier Unciti-Broceta、Mark Bradley

  DOI：10.1016/j.bmcl.2012.07.101

  日期：2012.9

  Variation at the 3' position of fluorescein via Suzuki-Miyaura cross-coupling with aryl and heteroaryl moieties gave a family of anthofluoresceins whose spectroscopic properties were studied. The 1-methylindole derivative gave the highest quantum yield and was observed to behave as a molecular rotor, displaying marked variations in fluorescent intensities with viscosity and offering possible application in cellular sensing and fluorescent polarisation assays. (c) 2012 Elsevier Ltd. All rights reserved.
• A fluorescein-derived anthocyanidin-inspired pH sensor
  作者：Asier Unciti-Broceta、M. Rahimi Yusop、Patricia R. Richardson、Jeffrey G.A. Walton、Mark Bradley

  DOI：10.1016/j.tetlet.2009.03.223

  日期：2009.7

  A new multicolor pH-dependent fluorophore was synthesized via Pd-mediated cross-coupling chemistry of the mono-triflate of fluorescein with p-hydroxyphenylboronic acid. The novel indicator, named anthofluorescein, is highly sensitive to pH changes between 7 and 10 and displays a green to red fluorescence shift, making it a Valuable candidate for biological studies. (C) 2009 Elsevier Ltd. All rights reserved.