[(18)F]-4-phenylbutyl fluoride | 1133140-49-4

• 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: [(18)F]-4-phenylbutyl fluoride
• 英文别名: [(18)F](4-fluorobutyl)benzene；4-(18F)fluoranylbutylbenzene
• CAS: 1133140-49-4
• 化学式: C₁₀H₁₃F
• 分子量: 151.213
• InChiKey: MOJORFVCTWDLTP-KXMUYVCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4-phenylbutyl 4-methylbenzenesulfonate 在 potassium [¹⁸F]fluoride 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 [(18)F]-4-phenylbutyl fluoride
  参考文献：
  名称：

  [18F]氟化物离子的氟合成18F放射性示踪剂：亲核氟化作为标记过程。

  摘要：

  标签小组：发现[ 18 F]氟离子对氟代磺酸盐进行氟脱标记是制备各种18 F标记的修复基团和已知放射性示踪剂的有利策略（参见图片）。荧光固相萃取（FSPE）用于从标记的材料中分离出过量的氟前体，这表明可以避免传统的纯化方案，例如蒸馏或繁琐的分离。

  DOI：

  10.1002/anie.200803897

文献信息

• Use of perfluoro groups in nucleophilic¹⁸F-fluorination
  作者：Elisabeth Blom、Farhad Karimi、Bengt LÃ¥ngström

  DOI：10.1002/jlcr.1695

  日期：——

  Substrates with leaving groups that contained perfluoro moieties were investigated in labelling chemistry in order to exploit their properties to improve reactivity and purification. [18F](Fluoromethyl)benzene was used as the model target compound. Precursors containing perfluoroalkyl and perfluoroaryl sulfonate moieties were subjected to nucleophilic 18F-fluorination, and the impact of perfluoro groups on the substitution reaction and product purification was investigated. [18F]Fluoride interacted with perfluoroalkyl chains, precluding nucleophilic substitution. When perfluoroaryl groups were used, the substitution proceeded, and the separation of product was explored. The radiolabelled product was obtained in 32% analytical yield and the radiochemical purity was increased to approximately 77% using fluorous solid phase extraction purification. Copyright © 2009 John Wiley & Sons, Ltd.

  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.
• [EN] PREPARATION OF FLUORINE-LABELLED COMPOUNDS<br/>[FR] PRÉPARATION DE COMPOSÉS MARQUÉS PAR DU FLUOR
  申请人：ISIS INNOVATION

  公开号：WO2010007363A3

  公开（公告）日：2010-07-01
• 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.
• METAL OXIDE CATALYZED RADIOFLUORINATION
  申请人：The Regents of the University of California

  公开号：US20170224851A1

  公开（公告）日：2017-08-10

  Inter alia, the first titania-catalyzed [ 18 F]-radiofluorination in highly aqueous medium is provided. In embodiments, the method utilizes titanium dioxide, 1:1 acetonitrile-thexyl alcohol solvent mixture and tetrabutylammonium bicarbonate as a base. Radiolabeling may be directly performed with aqueous [ 18 F]fluoride without the need for drying/azeotroping step, which reduces radiosynthesis time while keeping high fluoride conversion. The general applicability of the synthetic strategy to the synthesis of the wide range of PET probes from tosylated precursors is demonstrated.
• US9895454B2
  申请人：——

  公开号：US9895454B2

  公开（公告）日：2018-02-20