benzyl<18F>fluoride | 7618-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl<18F>fluoride
• 英文别名: [(18)F](fluoromethyl)benzene；[¹⁸F]fluoromethyl-benzene；[18F]fluoromethyl benzene；(18)F-benzyl fluoride；<¹⁸F>-Benzylfluorid；(18F)fluoranylmethylbenzene
• CAS: 7618-03-3
• 化学式: C₇H₇F
• 分子量: 109.133
• InChiKey: MBXXQYJBFRRFCK-COJKEBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  benzyl pentafluorobenzenesulfonate 在 Kryptofix222[18F]钾盐 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 benzyl<18F>fluoride
  参考文献：
  名称：

  Use of perfluoro groups in nucleophilic¹⁸F-fluorination

  摘要：

  含有全氟基团的离去基底在标记化学中进行了研究，以利用其特性提高反应性和纯化。以[18F](氟甲基)苯作为模型目标化合物。含有全氟烷基和全氟芳基磺酸基团的前体经过亲核性18F-氟化，研究了全氟基团对取代反应和产物纯化的影响。[18F]氟化物与全氟烷基链发生相互作用，妨碍了亲核取代反应。当使用全氟芳基基团时，取代反应得以进行，并探讨了产物的分离。最终获得了32%的分析产率，并通过氟固相萃取纯化将放射化学纯度提高至约77%。版权所有 © 2009 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1695

文献信息

• METHODS FOR SILVER-PROMOTED FLUORINATION OF ORGANIC MOLECULES
  申请人：Caires Christopher C.

  公开号：US20100152502A1

  公开（公告）日：2010-06-17

  The methods of the disclosure may be used for the fluorination of organic compounds, and in particular aryl organic compounds other than just benzyl halogens. It is within the scope of the present disclosure, for organic compounds comprising an electrophilic carbon atom and a halogen leaving group to be fluorinated by the methods of the disclosure. One aspect of the disclosure provides methods of introducing a fluorine atom onto an electrophilic carbon atom, comprising mixing an insoluble basic silver salt, an organic molecule containing a leaving group, an aqueous solution of hydrofluoric acid, and a polar solvent:water composition; incubating said mixture at a temperature of about 20° C. to about 35° C., thereby obtaining a fluorinated organic product.

  披露的方法可用于有机化合物的氟化，特别是不仅限于苄卤素的芳基有机化合物。根据本公开，包括带有亲电碳原子和卤素离去基团的有机化合物可通过披露的方法进行氟化。披露的一个方面提供了一种将氟原子引入亲电碳原子的方法，包括混合不溶性碱性银盐、含有离去基团的有机分子、氢氟酸水溶液和极性溶剂：水组成物；将所述混合物孵育在约20°C至约35°C的温度下，从而获得氟化有机产物。
• 18F-LABELED AZIDE COMPOUND, REAGENT FOR 18F-LABELING AND METHOD FOR 18F-LABELING OF ALKYNE COMPOUND USING SAME
  申请人：Watanabe Yasuyoshi

  公开号：US20120101266A1

  公开（公告）日：2012-04-26

  [OBJECT] The present invention provides an 18 F-labeled azide compound usable in the Huisgen reaction which enables 18 F-labeling although only a small quantity of alkyne compound is available as a counterpart substrate, more specifically the 18 F-labeled azide compound enabling the PET to be applied to peptides or oligonucleotides and enabling the 18 F-labeling of any sites of oligonucleotide other than the 5′ end or 3′ end thereof, a reagent for 18 F-labeling, and a method for 18 F -labeling of an alkyne compound using the same. [SOLVING MEANS] An 18 F-labeled azide compound according to the present invention is expressed by the following structural formula 1. [SELECTED DRAWING] None

  本发明提供了一种18F标记的叠氮化合物，可用于Huisgen反应，即使只有少量炔化合物作为对应底物，也能进行18F标记。具体而言，该18F标记的叠氮化合物使PET技术能够应用于肽或寡核苷酸，并且能够在寡核苷酸的5'端或3'端之外的任何位点进行18F标记，还提供了用于18F标记的试剂，以及使用该试剂对炔化合物进行18F标记的方法。根据本发明，所述的18F标记的叠氮化合物可由以下结构式1表示。
• Electrophilic radiofluorination of aryltrimethylsilanes as a general route to 18F-labeled aryl fluorides
  作者：M. Speranza、C.-Y. Shiue、A.P. Wolf、D.S. Wilbur、G. Angelini

  DOI：10.1016/s0022-1139(00)80525-4

  日期：1985.10

  The reactions of a variety of aryltrimethylsilanes with elemental fluorine and acetyl hypofluorite have been studied with the aim of developing a general method for labeling aromatic compounds with fluorine-18. Extensive 18F incorporation into the aromatic ring of the selected aryltrimethylsilanes was invariably observed, leading to the ipso (18F-for-Si) electrophilic substitution products together

  为了开发一种用氟18标记芳族化合物的通用方法，已经研究了各种芳基三甲基硅烷与元素氟和乙酰基次萤石的反应。广泛18 ˚F掺入选定aryltrimethylsilanes的芳香环总是观察到，导致本位（18 F-换Si）的亲电取代产物连同其他（可变产率18 F-用于-H）电取代产物。18的相对范围发现F的取代过程[（（C 1 -Si / C 1 -H）]，主要取决于底物芳环上的取代基，离去部分和所用的放射性氟化方法。讨论了芳基三甲基甲硅烷基衍生物作为快速合成18 F标记的放射性药物的高比活性的前体的用途。
• IODINE RADIOLABELLING METHOD
  申请人：Avory Michelle

  公开号：US20120237444A1

  公开（公告）日：2012-09-20

  The present invention provides a novel method of labelling biological targeting molecules (BTMs) of interest with radioiodine. Also provided are novel radioiodinated BTMs prepared using the method, as well as radiopharmaceutical compositions comprising such radioiodinated BTMs. The invention also provides radioiodinated intermediates useful in the method, as well as in vivo imaging methods using the radioiodinated BTMs.

  本发明提供了一种新的方法，用放射性碘标记感兴趣的生物靶向分子（BTMs）。还提供了使用该方法制备的新型放射性碘化BTMs，以及包含这种放射性碘化BTMs的放射性制剂组合物。本发明还提供了在该方法中有用的放射性碘化中间体，以及使用放射性碘化BTMs的体内成像方法。
• Titania-Catalyzed Radiofluorination of Tosylated Precursors in Highly Aqueous Medium
  作者：Maxim E. Sergeev、Federica Morgia、Mark Lazari、Christopher Wang、R. Michael van Dam

  DOI：10.1021/jacs.5b02659

  日期：2015.5.6

  Nucleophilic radiofluorination is an efficient synthetic route to many positron-emission tomography (PET) probes, but removal of water to activate the cyclotron-produced [F-18]fluoride has to be performed prior to reaction, which significantly increases overall radiolabeling time and causes radioactivity loss. In this report, we demonstrate the possibility of F-18-radiofluorination in highly aqueous medium. The method utilizes titania nanoparticles, 1:1 (v/v) acetonitrile-thexyl alcohol solvent mixture, and tetra-n-butylammonium bicarbonate as a phase-transfer agent. Efficient radiolabeling is directly performed with aqueous [F-18]fluoride without the need for a drying/azeotroping step to significantly reduce radiosynthesis time. High radiochemical purity of the target compound is also achieved. The substrate scope of the synthetic strategy is demonstrated with a range of aromatic, aliphatic, and cydoaliphatic tosylated precursors.