ethyl 2-(6-(2-(tert-butoxy)-2-oxoethoxy)-3-oxo-3H-xanthen-9-yl)benzoate | 191791-14-7

• 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: ethyl 2-(6-(2-(tert-butoxy)-2-oxoethoxy)-3-oxo-3H-xanthen-9-yl)benzoate
• 英文别名: 6-O-(tert-butoxycarbonylmethyl)fluorescein ethyl ester；Ethyl 2-[3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]-6-oxoxanthen-9-yl]benzoate
• CAS: 191791-14-7
• 化学式: C₂₈H₂₆O₇
• 分子量: 474.51
• InChiKey: IKSJVEXHAPFPLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-(6-(2-(tert-butoxy)-2-oxoethoxy)-3-oxo-3H-xanthen-9-yl)benzoate 在 三氟乙酸 作用下， 反应 1.0h， 以99%的产率得到6-O-(carboxymethyl)fluorescein ethyl ester
  参考文献：
  名称：

  荧光探针监测细胞磷脂酶A2的活性

  摘要：

  合成了带有一个或两个连接在烷基链末端的荧光基团的花生四烯酸衍生物，并显示出其作为抑制剂和底物探针的功能。

  DOI：

  10.1039/c6cc09305a
• 作为产物：
  描述：

  fluorescein free acid 在 硫酸 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 ethyl 2-(6-(2-(tert-butoxy)-2-oxoethoxy)-3-oxo-3H-xanthen-9-yl)benzoate
  参考文献：
  名称：

  荧光探针监测细胞磷脂酶A2的活性

  摘要：

  合成了带有一个或两个连接在烷基链末端的荧光基团的花生四烯酸衍生物，并显示出其作为抑制剂和底物探针的功能。

  DOI：

  10.1039/c6cc09305a

文献信息

• A new selective fluorogenic probe for trivalent cations
  作者：Andrea Barba-Bon、Ana M. Costero、Salvador Gil、Margarita Parra、Juan Soto、Ramón Martínez-Máñez、Félix Sancenón

  DOI：10.1039/c2cc17184h

  日期：——

  A new selective chromo-fluorogenic probe for Fe3+, Cr3+ and Al3+ is reported. Detection limits are in the μM range and the fluorogenic sensing ability could be observed by the naked eye when illuminated with UV-light. No response is observed with divalent cations.

  报告了一种新的选择性变色荧光探针，用于检测Fe3+、Cr3+和Al3+。检测限在微摩尔范围内，当用紫外光照射时，可用肉眼观察到荧光响应。二价阳离子未观察到反应。
• Synthesis of SERS active nanoparticles for detection of biomolecules
  作者：Joanna Wrzesien、Duncan Graham

  DOI：10.1016/j.tet.2011.11.053

  日期：2012.1

  Surface Enhanced Raman Scattering (SERS) can be used to detect specific DNA sequences by methods based on hybridisation of oligonucleotide functionalized nanoparticles to complementary DNA sequences. The problem, which has to be overcome to use this technique is that DNA is not strongly SERS active. This is due to the lack of a visible chromophore and presence of the highly negatively charged phosphate backbone, which prevents the electrostatic interaction with the metal surface necessary for the enhancement. To obtain SERS active DNA a label containing a surface seeking group, to allow adsorption of DNA on a metal surface, and a chromophore has to be attached to the DNA strand. Here we report the synthesis of three linkers containing a Raman tag [the following fluorophores were used for this purpose due to the fluorescence quenching ability of metallic nanoparticles: fluorescein, 6-aminofluorescein and tetramethylrhodamine (TAMRA)], surface complexing group (cyclic disulphide thioctic acid) and a chemical functionality for attachment of DNA (carboxyl group). Each of the linkers also contain poly(ethylene glycol) (PEG) (3 mer), which reduces non-specific adsorption of molecules to the surface of the nanoparticles and provides colloidal stability. The synthesized linkers were used to functionalize gold citrate (18 and 50 nm), silver citrate (40 nm) and silver EDTA (35 nm) nanoparticles. All of the conjugates exhibit high stability, gave good SERS responses at laser excitation frequencies of 514 and 633 nm and could be conjugated to amino-modified oligonucleotides in the presence of the commonly used (N-(3-dimethylaminopropyl)-N'-ethyl carbodiimide hydrochloride-EDC center dot HCl with N-hydroxysulfosuccinimide or 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride-DMT MM, which has not been used for bioconjugate preparation previously. This approach is less time consuming and less expensive than previously used protocols and does not require the formation of a mixed layer of oligonucleotides and Raman reporter on the metal surface. Additionally the presence of a reactive functionality within the linker structure makes it possible to conjugate the linker to other biomolecules of interest such as proteins. (C) 2011 Elsevier Ltd. All rights reserved.