3-[¹⁸F]fluoro-5-[(pyridin-3-yl)ethynyl]benzo-nitrile | 686768-17-2

• 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: 3-[¹⁸F]fluoro-5-[(pyridin-3-yl)ethynyl]benzo-nitrile
• 英文别名: F-Peb F-18；3-(18F)fluoranyl-5-(2-pyridin-2-ylethynyl)benzonitrile
• CAS: 686768-17-2
• 化学式: C₁₄H₇FN₂
• 分子量: 221.223
• InChiKey: MEZOEZSKPXUIJA-HUYCHCPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(2-(吡啶-2-基)乙炔基)-5-硝基苯甲腈 在 potassium [¹⁸F]fluoride 、 potassium carbonate 、 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 二甲基亚砜 为溶剂， 反应 0.08h， 以69.4%的产率得到3-[¹⁸F]fluoro-5-[(pyridin-3-yl)ethynyl]benzo-nitrile
  参考文献：
  名称：

  Effect of Leaving Group Substituents on the Microfluidic Synthesis of [18F]3-Fluoro-5-[(pyridin-3-yl)ethynyl]benzonitrile ([18F]FPEB)

  摘要：

  A commercial microfluidic reactor system has been used to synthesize the mGLUR5 receptor imaging agent [F-18]FPEB. To study the effect of leaving group substituents on the synthesis of the desired compound, the chloro-, bromo-, iodo-, and nitro-substituted precursors for FPEB were evaluated. Precursor concentrations of 4 - 10 mg/mL were evaluated in various solvents, with temperature ranges between 120 and 220 degrees C, and total processing times of less than five minutes. Optimized incorporation yields ranged from 5% to 69.4% depending on the precursor used.

  DOI：

  10.3987/com-16-s(s)49

文献信息

• Alkyne derivatives as tracers for metabotropic glutamate receptor binding
  申请人：Cosford Peter Nicholas David

  公开号：US20070060618A1

  公开（公告）日：2007-03-15

  The present invention is directed to isotopically labeled alkyne derivative compounds, particularly 11 C, 13 C, 14 C, 18 F, 15 O, 13 N, 35 S, 2 H, and 3 H labeled compounds. In particular, the present invention is directed to 11 C, 13 C, 14 C, 18 F, 15 O, 13 N, 35 S, 2 H, and 3 H labeled heterocyclic alkynes and methods of their preparation. The present invention further includes a method of use of the 11 C, 18 F, 15 O, or 13 N labeled heterocyclic alkyne compounds as tracers in positron emission tomography (PET) imaging, particularly in the study of metabolic conditions in mammals, specifically conditions modulated by metabotropic glutamate receptors subtype 5 (mGluR5).

  本发明涉及同位素标记的炔基衍生物化合物，特别是11C、13C、14C、18F、15O、13N、35S、2H和3H标记的化合物。具体而言，本发明涉及11C、13C、14C、18F、15O、13N、35S、2H和3H标记的杂环炔烃及其制备方法。本发明还包括将11C、18F、15O或13N标记的杂环炔烃化合物用作正电子发射断层扫描（PET）成像中的示踪剂的使用方法，特别是在哺乳动物代谢状况的研究中，特别是通过代谢型谷氨酸受体亚型5（mGluR5）调节的状况。
• Copper-Mediated Radiofluorination of Arylstannanes with [¹⁸F]KF
  作者：Katarina J. Makaravage、Allen F. Brooks、Andrew V. Mossine、Melanie S. Sanford、Peter J. H. Scott

  DOI：10.1021/acs.orglett.6b02911

  日期：2016.10.21

  A copper-mediated nucleophilic radiofluorination of aryl- and vinylstannanes with [18F]KF is described. This method is fast, uses commercially available reagents, and is compatible with both electron-rich and electron-deficient arene substrates. This method has been applied to the manual synthesis of a variety of clinically relevant radiotracers including protected [18F]F-phenylalanine and [18F]F-DOPA

  描述了用[ 18 F] KF进行的铜介导的芳基和乙烯基锡烷的亲核放射性氟化反应。该方法快速，使用可商购的试剂，并且与富电子和缺电子的芳烃底物兼容。该方法已应用于人工合成各种临床相关的放射性示踪剂，包括受保护的[ 18 F] F-苯丙氨酸和[ 18 F] F-DOPA。另外，已证明[ 18 F] MPPF的自动合成可提供200±20 mCi的临床验证剂量，并具有2400±900 Ci / mmol的高比活度。
• Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic ¹⁸F-Fluorination
  作者：Thibault Gendron、Kerstin Sander、Klaudia Cybulska、Laure Benhamou、Pak Kwan Brian Sin、Aqsa Khan、Michael Wood、Michael J. Porter、Erik Årstad

  DOI：10.1021/jacs.8b06730

  日期：2018.9.5

  Herein, we report a novel intramolecular ring-closing reaction of biaryl thioethers that give access to highly functionalized dibenzothiophene sulfonium salts under mild conditions. The resulting precursors react regioselectively with [18F]fluoride to give [18F]fluoroarenes in predictable radiochemical yields. The strategy expands the available radiochemical space and provides superior labeling efficiency

  在此，我们报道了联芳基硫醚的一种新型分子内闭环反应，该反应可以在温和条件下获得高度官能化的二苯并噻吩锍盐。所得前体与[ 18 F]氟化物发生区域选择性反应，以可预测的放射化学产率生成[ 18 F]氟芳烃。该策略扩大了可用的放射化学空间，并为临床相关 PET 示踪剂提供了卓越的标记效率。
• Enhanced copper-mediated ¹⁸F-fluorination of aryl boronic esters provides eight radiotracers for PET applications
  作者：Sean Preshlock、Samuel Calderwood、Stefan Verhoog、Matthew Tredwell、Mickael Huiban、Antje Hienzsch、Stefan Gruber、Thomas C. Wilson、Nicholas J. Taylor、Thomas Cailly、Michael Schedler、Thomas Lee Collier、Jan Passchier、René Smits、Jan Mollitor、Alexander Hoepping、Marco Mueller、Christophe Genicot、Joël Mercier、Véronique Gouverneur

  DOI：10.1039/c6cc03295h

  日期：——

  Eight clinically relevant radiotracers were isolated applying a Cu-mediated non-carrier added nucleophilic ¹⁸F-fluorination of arylboronic ester precursors.

  使用铜介导的非载体添加亲核性¹⁸F-氟化技术，从芳基硼酸酯前体中分离出了八种临床相关的放射性示踪剂。
• Radiosynthesis of SPECT tracers via a copper mediated ¹²³I iodination of (hetero)aryl boron reagents
  作者：Thomas C. Wilson、Greg McSweeney、Sean Preshlock、Stefan Verhoog、Matthew Tredwell、Thomas Cailly、Véronique Gouverneur

  DOI：10.1039/c6cc07417k

  日期：——

  The Cu-mediated [¹²³I]iodination of aryl boronic pinacol esters and acids exhibits broad scope and is successfully applied to the labelling of four radiotracers, [¹²³I]DPA-713, [¹²³I]IMPY, [¹²³I]MIBG and [¹²³I]IPEB.

  芳基硼酸皮纳科酯和酸的Cu介导的[¹²³I]碘化反应具有广泛的适用范围，并成功应用于四种放射示踪剂的标记，[¹²³I]DPA-713，[¹²³I]IMPY，[¹²³I]MIBG和[¹²³I]IPEB。