ethyl 2-[¹⁸F]fluorobenzoate | 1656990-87-2

• 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: ethyl 2-[¹⁸F]fluorobenzoate
• 英文别名: [¹⁸F]2FBA-OEt；ethyl 2-(18F)fluoranylbenzoate
• CAS: 1656990-87-2
• 化学式: C₉H₉FO₂
• 分子量: 167.169
• InChiKey: RUWPGPOBTHOLHF-LMANFOLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙氧羰基苯硼酸频哪醇酯 在 Cu(OTf)₂(impy)₄ 、 四甲基氢氧化铵 、 tetramethylammonium [18F]fluoride 作用下， 以 乙腈 为溶剂， 以100 %的产率得到ethyl 2-[¹⁸F]fluorobenzoate
  参考文献：
  名称：

  定向基团辅助、铜介导的放射性氟化和[18F]Olaparib放射合成的探索

  摘要：

  有机硼前体的铜介导放射性氟化 (CMRF) 是作为正电子发射断层扫描 (PET) 放射性示踪剂的芳香族化合物后期放射性氟化的首选方法。然而，CMRF 通常需要苛刻的反应条件、大量的底物和苛刻的溶剂（例如 DMA）才能进行，从而提供可变的放射化学产率（RCY）。使用[ 18 F]甲苯磺酰氟作为[ 18 F]氟化物的来源，我们发现了有机硼前体的高效CMRF，并在邻位的导向基团（DG）的辅助下。该反应可以在乙腈中在温和条件下（甚至在室温下）进行，并产生高RCY，为芳香族化合物的放射性氟化提供了一种新的策略。对这一策略的探索也提供了有关 CMRF 副反应的更多信息。利用该策略，[ 18 F]olaparib 已以高 RCY 进行放射合成，具有高摩尔活性以及高化学和放射化学纯度，证明了 DG 辅助 CMRF 在制备18 F 标记 PET 放射性示踪剂方面的巨大潜力。

  DOI：

  10.1021/acsmedchemlett.3c00465

文献信息

• Catalyst-Free Aromatic Radiofluorination via Oxidized Iodoarene Precursors
  作者：Young-Do Kwon、Jeongmin Son、Joong-Hyun Chun

  DOI：10.1021/acs.orglett.8b03450

  日期：2018.12.21

  Oxidized iodoarenes (OIAs), prepared via mCPBA-mediated oxidation, have been demonstrated as versatile precursors for the synthesis of [18F]fluoroarenes in the absence of catalysts. OIAs have been identified as intermediates in single-pot syntheses of iodonium salts and ylides but have never been recognized as radiofluorination precursors. Here, the isolated OIAs were used without any catalysts to

  氧化iodoarenes（OIAs），通过制备米CPBA介导的氧化，已经被证明是通用于[合成前体18 F]在不存在催化剂的fluoroarenes。OIAs已被确定为碘盐和碘化物单罐合成的中间体，但从未被认为是放射性氟化的前体。在这里，分离的OIAs无需任何催化剂即可用于生产官能化的[ 18 F]氟代芳烃，而与芳烃的电子性质无关。该方法还用于放射性标记合成子的生产，用作芳族18 F标记的构建基块。
• A General Copper-Mediated Nucleophilic¹⁸F Fluorination of Arenes
  作者：Matthew Tredwell、Sean M. Preshlock、Nicholas J. Taylor、Stefan Gruber、Mickael Huiban、Jan Passchier、Joël Mercier、Christophe Génicot、Véronique Gouverneur

  DOI：10.1002/anie.201404436

  日期：2014.7.21

  describe the realization of these requirements with the production of 18F arenes from pinacol‐derived aryl boronic esters (arylBPin) upon treatment with [18F]KF/K222 and [Cu(OTf)2(py)4] (OTf=trifluoromethanesulfonate, py=pyridine). This method tolerates electron‐poor and electron‐rich arenes and various functional groups, and allows access to 6‐[18F]fluoro‐L‐DOPA, 6‐[18F]fluoro‐m‐tyrosine, and the translocator

  标有氟18的分子用作正电子发射断层扫描的放射性示踪剂。一个重要的挑战是芳烃不适于芳香亲核取代（S的标记Ñ AR）与[ 18 F]˚F - 。在理想情况下，这些底物的18 F氟化反应将通过[ 18 F] KF与耐贮存稳定且易于获得的前体进行反应，并采用适用于自动化的广泛应用的方法。在此，我们描述了实现这些要求的生产的18个处理后从频哪醇衍生的芳基硼酸酯（arylBPin）的F芳烃与[ 18 F] KF / K 222和物[Cu（OTF）2（py）4 ]（OTf ＝三氟甲磺酸盐，py ＝吡啶）。此方法容许贫电子和富电子的芳烃和各种官能团，并允许访问6- [ 18 F]氟-大号-DOPA，6- [ 18 F]氟-米-酪氨酸，和转运蛋白（TSPO ）PET配体[ 18 F] DAA1106。
• Exploration of alcohol‐enhanced Cu‐mediated radiofluorination toward practical labeling
  作者：Dong Zhou、Wenhua Chu、John A. Katzenellenbogen

  DOI：10.1002/jlcr.3955

  日期：2022.1

  nucleophilic radiofluorination using a variety of model reactions in which we varied the concentration of [18F]fluoride (no carrier added or isotope diluted) and the amount of precursor, base, and Cu(OTF)2(Py)4. We found that lower amounts of precursors (e.g., 15 μmol) could be used and that the amount of base (e.g., K2CO3 or KHCO3) played a critical and limiting role in the labeling reactions. Greater

  使用硼前体的铜介导的亲核放射氟化是一种很有前途的通用方法，可以用 [ 18 F] 氟化物标记芳香族化合物。然而，在各种报告中，需要大量前体（60 μmol）才能实现高放射化学转化率（RCC），这对于制备18 F放射性药物既不理想也不实用。为了研究这个问题，我们使用各种模型反应研究了醇增强的 Cu 介导的亲核放射氟化，在这些反应中我们改变了 [ 18 F] 氟化物的浓度（不添加载体或稀释同位素）和前体、碱和和的量。 Cu(OTF) 2 (Py) 4. 我们发现可以使用较低量的前体（例如，15 μmol），并且碱的量（例如，K 2 CO 3或 KHCO 3）在标记反应中起着关键和限制作用。需要大于一当量的碱和足量的前体和 Cu(OTf) 2 (Py) 4才能实现良好到高的 RCC。RCC 还取决于标记反应的总浓度，首选低反应体积和高浓度的试剂。我们的研究结果将有助于改进放射性标记方案的设计，该
• Molecular Imaging of Sirtuin1 Expression–Activity in Rat Brain Using Positron-Emission Tomography–Magnetic-Resonance Imaging with [¹⁸F]-2-Fluorobenzoylaminohexanoicanilide
  作者：Robin Bonomi、Vadim Popov、Maxwell T. Laws、David Gelovani、Anjoy Majhi、Aleksandr Shavrin、Xin Lu、Otto Muzik、Nashaat Turkman、Renshyan Liu、Thomas Mangner、Juri G. Gelovani

  DOI：10.1021/acs.jmedchem.8b00253

  日期：2018.8.23

  Sirtuin 1 (SIRT1) is a class III histone deacetylase that plays significant roles in the regulation of lifespan, metabolism, memory, and circadian rhythms and in the mechanisms of many diseases. However, methods of monitoring the pharmacodynamics of SIRT1-targeted drugs are limited to blood sampling because of the invasive nature of biopsies. For the noninvasive monitoring of the spatial and temporal dynamics of SIRT1 expression-activity in vivo by PET-CT-MRI, we developed a novel substrate-type radio tracer, [F-18]-2-fluorobenzoylaminohexanoicanilide (2-[F-18]BzAHA). PET-CT-MRI studies in rats demonstrated increased accumulation of 2-[F-18]BzAHA-derived radioactivity in the hypothalamus, hippocampus, nucleus accumbens, and locus coeruleus, consistent with autoradiographic and immunofluorescent (IMF) analyses of brain-tissue sections. Pretreatment with the SIRT1 specific inhibitor, EX-527 (5 mg/kg, ip), resulted in about a 20% reduction of 2-[F-18]BzAHA-derived-radioactivity accumulation in these structures. In vivo imaging of SIRT1 expression-activity should facilitate studies that improve the understanding of SIRT1-mediated regulation in the brain and aid in the development and clinical translation of SIRT1-targeted therapies.
• FLUORINATION METHOD
  申请人：Oxford University Innovation Limited

  公开号：US20170137341A1

  公开（公告）日：2017-05-18

  The present invention relates to a process for producing an organic compound comprising an 18 F atom. The compounds comprising an 18 F can be useful as PET ligands for use in diagnostics and/or scanning. The process of the invention comprises treating an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp 2 hybridised carbon atom, with (i) 18 F— and (ii) a copper compound. The invention also provides the use of an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp 2 hybridised carbon atom, in a process for producing an organic compound comprising an 18 F atom, which process comprises treating the organoboron compound with (i) 18 F— and (ii) a copper compound. The invention also provides a compound of formula (XXXVII): wherein: each PG A is independently H or an alcohol protecting group; PG B is H or a carboxylic acid protecting group; each PG C is independently an amine protecting group; Z is a group selected from a boronic ester group, a boronic acid group, a borate group, and a trifluoroborate group; and a is an integer from 0 to 4.