[carbonyl-¹¹C]N,N'-diphenylurea

• 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: [carbonyl-¹¹C]N,N'-diphenylurea
• 英文别名: 1,3-diphenyl-[11C]urea；N,N'-diphenyl[11C]urea；[11C]diphenylurea；11C-labeled diphenylurea；1,3-diphenyl(11C)urea
• 化学式: C₁₃H₁₂N₂O
• 分子量: 211.24
• InChiKey: GWEHVDNNLFDJLR-HSGWXFLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 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：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  [11C]二氧化碳 、 苯胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三丁基膦 、 偶氮二甲酸二叔丁酯 作用下， 以 乙腈 为溶剂， 反应 0.09h， 以79%的产率得到[carbonyl-¹¹C]N,N'-diphenylurea
  参考文献：
  名称：

  Synthesis of 11C-Labelled Symmetrical Ureas via the Rapid Incorporation of [11C]CO2 into Aliphatic and Aromatic Amines

  摘要：

  An efficient method to radiolabel symmetrical [C-11] ureas using 1,8-diazabicycloundec-7-ene (DBU) and cyclotron-produced [C-11]CO2 has been developed. [C-11] urea derivatives were obtained when aliphatic and aromatic amines were used with excellent radiochemical yields (RCYs) of over 70%. The mechanism of the reaction is proposed on the basis of control experiments. This simple and robust methodology provides a powerful tool to prepare C-11-labelled ureas previously inaccessible by existing methods and enable their utilisation for in vivo molecular imaging applications.

  DOI：

  10.1055/s-0034-1381055

文献信息

• [EN] METHODS FOR CARBON ISOTOPE LABELING SYNTHESIS BY RHODIUM-PROMOTED CARBONYLATION VIA ISOCYANATE USING AZIDES AND CARBON-ISOTOPE MONOXIDE<br/>[FR] PROCEDES POUR LA SYNTHESE DE MARQUAGE PAR ISOTOPE DU CARBONE REALISEE PAR CARBONYLATION, CATALYSEE PAR DU RHODIUM, PAR L'INTERMEDIAIRE D'ISOCYANATE, AU MOYEN D'AZIDES ET DE MONOXYDE D'ISOTOPE DE CARBONE
  申请人：GE HEALTHCARE LTD

  公开号：WO2005061445A1

  公开（公告）日：2005-07-07

  Methods and reagents for rhodium-promoted carbonylation via isocyanate using carbon-isotope labeled carbon monoxide are provided. The resultant carbon­ isotope labeled compounds are useful as radiopharmaceuticals, especially for use in Positron Emission Tomography (PET). Associated kits for PET studies are also provided.

  提供了通过异氰酸酯使用碳同位素标记的一氧化碳促进的钯催化羰基化的方法和试剂。所得的碳同位素标记化合物可用作放射性药物，特别适用于正电子发射断层扫描（PET）。还提供了用于PET研究的相关试剂盒。
• One-pot synthesis of [11C]ureas via triphenylphosphinimines
  作者：Erica W. van Tilburg、Albert D. Windhorst、Margreet van der Mey、Jacobus D. M. Herscheid

  DOI：10.1002/jlcr.1052

  日期：2006.3.30

  A series of 11C-labeled ureas was prepared using a rapid and efficient one-pot procedure. First, the intermediate [11C]phenylisocyanate was formed with phenyltriphenylphosphinimine and [11C]CO2. A range of amines was then reacted with the [11C]phenylisocyanate yielding the [11C]urea derivatives in short synthesis times. This easy-to-handle method circumvents disadvantages of known procedures and generates the possibility to prepare other kinds of 11C-labeled compounds using a variety of phenylphosphinimines in combination with different nucleophiles. The presented approach is an alternative to the use of established methods in 11C-labeling chemistry. Copyright © 2006 John Wiley & Sons, Ltd.

  一系列11C标记的尿素是通过一个快速且高效的一锅法程序制备的。首先，中间体[11C]苯异氰酸酯由苯基三苯基膦亚胺和[11C]CO2形成。接着，一系列胺与[11C]苯异氰酸酯反应，在短合成时间内得到[11C]尿素衍生物。这种易于操作的方法避免了已知程序的缺点，并开启了利用多种苯基膦亚胺与不同亲核试剂结合制备其他类型11C标记化合物的可能性。所提出的方法为11C标记化学中已建立的方法提供了替代方案。版权所有 © 2006 John Wiley & Sons, Ltd.
• Palladium-mediated oxidative carbonylation reactions for the synthesis of¹¹C-radiolabelled ureas
  作者：Steven Kealey、Stephen M. Husbands、Idriss Bennacef、Antony D. Gee、Jan Passchier

  DOI：10.1002/jlcr.3151

  日期：2014.4

  Palladium(II)-mediated oxidative carbonylation reactions have been used to synthesize 11C-radiolabelled ureas via the coupling of amines with [11C]carbon monoxide, in a one-pot process. Following trapping of 11CO in a solution of copper(I) tris(3,5-dimethylpyrazolyl)borate, homocoupling reactions of primary aliphatic amines proceed in the presence of Pd(PPh3)2Cl2 to give the corresponding N,N-disubstituted [11C]ureas. Secondary amines do not produce the corresponding N,N,N,N-tetrasubsituted [11C]ureas under these conditions. This difference in reactivity allows for the formation of unsymmetrical N,N’,N’-trisubstituted [11C]ureas using a mixture of a primary amine and a reactive secondary amine. The potential use of this method in positron emission tomography (PET) was demonstrated by the synthesis of the M1 muscarinic acetylcholine receptor radiotracer, [11C-carbonyl]GSK1034702.

  钯(II)介导的氧化羰基化反应已被用于通过将胺与[11C]一氧化碳耦合，在一步法中合成11C放射性标记的脲类化合物。在将11CO捕获在铜(I)三(3,5-二甲基吡唑)硼酸盐溶液后，初级脂肪胺的同源偶联反应在Pd(PPh3)2Cl2的存在下进行，生成相应的N,N-二取代[11C]脲。次级胺在这些条件下不产生相应的N,N,N,N-四取代[11C]脲。这种反应性差异使得可以利用初级胺与反应性较强的次级胺的混合物形成不对称的N,N’,N’-三取代[11C]脲。通过合成M1毒蕈碱型乙酰胆碱受体放射性示踪剂[11C-羰基]GSK1034702，展示了该方法在正电子发射断层成像（PET）中的潜在应用。
• Synthesis of 11C-Labelled Ureas by Palladium(II)-Mediated Oxidative Carbonylation
  作者：Sara Roslin、Peter Brandt、Patrik Nordeman、Mats Larhed、Luke Odell、Jonas Eriksson

  DOI：10.3390/molecules22101688

  日期：——

  Positron emission tomography is an imaging technique with applications in clinical settings as well as in basic research for the study of biological processes. A PET tracer, a biologically active molecule where a positron-emitting radioisotope such as carbon-11 has been incorporated, is used for the studies. Development of robust methods for incorporation of the radioisotope is therefore of the utmost

  正电子发射断层扫描是一种成像技术，在临床环境以及生物学过程研究的基础研究中都有应用。PET示踪剂是一种生物活性分子，其中已掺入了发射正电子的放射性同位素，例如碳11。因此，开发用于掺入放射性同位素的鲁棒方法至关重要。尿素官能团存在于许多生物活性化合物中，因此是以[11C]一氧化碳形式掺入碳11的有吸引力的目标。以胺和[11C]一氧化碳为起始原料，通过钯（II）介导的氧化羰基化反应合成对称和不对称的11C标记的脲，并经衰变校正的放射化学产率高达65％。使用[11C]一氧化碳的附加优势通过可溶性环氧化物水解酶抑制剂的摩尔活性（247 GBq /μmol-319GBq /μmol）显示。发现DFT计算支持通过11 C-标记的异氰酸酯中间体进行的反应机理。
• Broad Scope and High‐Yield Access to Unsymmetrical Acyclic [ ¹¹ C]Ureas for Biomedical Imaging from [ ¹¹ C]Carbonyl Difluoride
  作者：Jimmy E. Jakobsson、Sanjay Telu、Shuiyu Lu、Susovan Jana、Victor W. Pike

  DOI：10.1002/chem.202100690

  日期：2021.7.16

  needed for labelling acyclic ureas with carbon-11 (t1/2=20.4 min) as potential radiotracers for biomedical imaging with positron emission tomography (PET). Herein, we describe the rapid and high-yield syntheses of unsymmetrical acyclic [11C]ureas under mild conditions (room temperature and within 7 min) using no-carrier-added [11C]carbonyl difluoride with aliphatic and aryl amines. This methodology is compatible

  需要有效的方法来用碳-11（ t 1/2 = 20.4 分钟）标记无环脲作为正电子发射断层扫描（PET）生物医学成像的潜在放射性示踪剂。在此，我们描述了在温和条件下（室温和7分钟内）使用无载体添加的[ 11 C]碳酰二氟与脂肪族和芳基胺快速高产地合成不对称无环[ 11 C]脲。该方法与底物胺中的不同官能团（例如羟基、羧基、氨基、酰胺基或吡啶基）兼容。标记过程通过假定的[ 11 C]氨基甲酰氟进行，对于伯胺则通过可分离的[ 11 C]异氰酸酯中间体进行。产生的不对称[ 11 C]脲具有可忽略量的不需要的对称[ 11 C]脲副产物。此外，整体标记方法可耐受微量水，并且通常中等至优异的产率显示出良好的重现性。 [ 11 C]二氟化碳在合成无环[ 11 C]脲作为PET生物医学成像的新型放射性示踪剂方面显示出非凡的应用前景。