2,2,2-tris(nonafluoro-tert-butoxymethyl)ethanol | 939056-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-tris(nonafluoro-tert-butoxymethyl)ethanol
• 英文别名: tris(perfluoro-t-butoxy) alcohol；3-[1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)propan-2-yl]oxy-2,2-bis[[1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl]oxymethyl]propan-1-ol
• CAS: 939056-16-3
• 化学式: C₁₇H₉F₂₇O₄
• 分子量: 790.213
• InChiKey: BHJGGMXDBWWYGL-UHFFFAOYSA-N

物化性质

• 沸点：
  419.2±45.0 °C(Predicted)
• 密度：
  1.669±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  48
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  2,2,2-tris(nonafluoro-tert-butoxymethyl)ethanol 在 sodium azide 、 四丁基氟化铵 、 potassium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 1-[2-[2-[2-(2-Azidoethoxy)ethoxy]ethoxy]ethoxy]-3-[1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl]oxy-2,2-bis[[1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl]oxymethyl]propane
  参考文献：
  名称：

  The design and synthesis of highly branched and spherically symmetric fluorinated oils and amphiles

  摘要：

  A new surfactant design principle, based on concepts borrowed from protein science, is proposed. Using this principle, a class of highly branched and spherically symmetric fluorinated oils and amphiles has been designed and synthesized, for potential applications in the construction of fluorocarbon nanoparticles. The Mitsunobu reaction was employed as the key step for introducing three perfluoro-tert-butoxyl groups into pentaerythritol derivatives with excellent yields and extremely simple isolation procedures. Due to the symmetric arrangement of the fluorine atoms, each fluorinated oil or amphile molecule gives one sharp singlet F-19 NMR signal. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.004
• 作为产物：
  描述：

  2-(羟甲基)-2-(苯基甲氧基甲基)丙烷-1,3-二醇 在 三氯化铝 、 4 A molecular sieve 、 苯甲醚 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 2,2,2-tris(nonafluoro-tert-butoxymethyl)ethanol
  参考文献：
  名称：

  The design and synthesis of highly branched and spherically symmetric fluorinated oils and amphiles

  摘要：

  A new surfactant design principle, based on concepts borrowed from protein science, is proposed. Using this principle, a class of highly branched and spherically symmetric fluorinated oils and amphiles has been designed and synthesized, for potential applications in the construction of fluorocarbon nanoparticles. The Mitsunobu reaction was employed as the key step for introducing three perfluoro-tert-butoxyl groups into pentaerythritol derivatives with excellent yields and extremely simple isolation procedures. Due to the symmetric arrangement of the fluorine atoms, each fluorinated oil or amphile molecule gives one sharp singlet F-19 NMR signal. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.004

文献信息

• The Design and Synthesis of Highly Branched and Spherically Symmetric Fluorinated Macrocyclic Chelators
  作者：Y. Yu、Zhong-Xing Jiang

  DOI：10.1055/s-2007-1000857

  日期：2008.1

  Two novel, highly fluorinated macrocyclic chelators with highly branched and spherically symmetric fluorocarbon moieties have been designed and efficiently synthesized. This is achieved by conjugating a spherically symmetric fluorocarbon moiety to the macrocyclic chelator DOTA, with or without a flexible oligo-oxyethylene linker between these two parts. As a result of the spherical symmetry, all 27 fluorine atoms in each fluorinated chelator give a sharp singlet 19F NMR signal. The hydrophilicity and the 19F relaxation behavior of fluorinated chelators can be modulated by the insertion of a flexible linker between the fluorocarbon moiety and the macrocyclic linker. These chelators serve as prototypes for 1H-19F dual nuclei magnetic resonance imaging agents.

  设计并高效合成了两种新型高度氟化的宏环螯合剂，它们具有高度分支且球形对称的氟碳部分。通过将一个球形对称的氟碳部分与宏环螯合剂DOTA结合，并在两者之间加入或不加入一个柔性的聚氧乙烯连接链，实现了这一合成。由于球形对称性，每个氟化螯合剂中的27个氟原子在19F核磁共振谱中产生一个尖锐的单峰信号。通过在氟碳部分和宏环连接链之间插入一个柔性连接链，可以调节氟化螯合剂的亲水性和19F弛豫行为。这些螯合剂作为1H-19F双核磁共振成像试剂的原型。
• 含有多氟烷基长链的非天然手性氨基酸化合物和其胺的酸盐、制备方法及用途
  申请人：天津大学

  公开号：CN109956880B

  公开（公告）日：2022-03-15

  本发明公开了多氟烷基长链非天然手性氨基酸、制备方法及其用途。具体而言，本发明提供一种含有多氟烷基长链的非天然手性氨基酸化合物(I)和其胺的酸盐；可用作氨基酸手性基元融合到多肽及蛋白质中，通过生物标记和分析来研究大分子动态生化过程。相对于天然手性氨基酸，制备的多氟烷基长链非天然手性氨基酸脂溶性高，生物相容性更好；制备的多氟烷基长链非天然手性氨基酸由于含有多氟官能团，引入多肽或蛋白质中，通过生物标记和分析来研究大分子动态生化过程。
• Small BODIPY Probes for Combined Dual¹⁹F MRI and Fluorescence Imaging
  作者：Anh Minh Huynh、Andreas Müller、Sonja M. Kessler、Sarah Henrikus、Caroline Hoffmann、Alexandra K. Kiemer、Arno Bücker、Gregor Jung

  DOI：10.1002/cmdc.201600120

  日期：2016.7.19

  potential for biological and medical applications. Herein we report the first design, synthesis, dual detection validation, and cytotoxic testing of four promising BODIPY dyes for dual 19F MRI–fluorescence detection. Using straightforward Steglich reactions, small fluorinated alcohols were easily covalently tethered to a BODIPY dye in high yields, leaving its fluorescence properties unaffected. The

  两种互补成像方式19 F磁共振成像（MRI）和荧光成像（FLI）的组合在生物学和医学应用中具有很高的潜力。我们在此报告了四种用于双19的有希望的BODIPY染料的首次设计，合成，双重检测验证和细胞毒性测试。F MRI –荧光检测。使用直接的Steglich反应，可以轻松地将小的氟化醇以高收率共价连接到BODIPY染料上，而使其荧光性质不受影响。用各种技术分析了合成的化合物，以证明其在双重成像中的潜在效用。如所期望的，试剂的化学和磁性等价的三氟甲基基团表现出单个NMR信号。所确定的纵向弛豫时间T 1和横向弛豫时间T 2都在较低的第二范围内，使得能够对四种化合物进行体外成像。最吉利双19F MRI荧光剂也已在9.4 T小动物断层扫描仪中的小鼠验尸中成功成像。用人细胞（原代HUVEC和HepG2细胞系）进行的毒理学测定也表明了进行动物试验的可能性。
• WO2007/112100
  申请人：——

  公开号：——

  公开（公告）日：——
• Fluorous Mixture Synthesis of Asymmetric Dendrimers
  作者：Zhong-Xing Jiang、Yihua Bruce Yu

  DOI：10.1021/jo100102a

  日期：2010.3.19

  A divergent fluorous mixture synthesis (FMS) of asymmetric fluorinated dendrimers has been developed. Four generations of fluorinated dendrimers with the same fluorinated moiety were prepared with high efficiency, yield, and purity. Comparison of the physicochemical properties of these dendrimers provided Valuable information for their application and future optimization. This strategy has not only provided a practical method for the synthesis and purification of dendrimers, but also established the possibility of utilizing the same fluorinated moiety for FMS.