4-[¹²⁵I]-iodoanisole | 84211-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[¹²⁵I]-iodoanisole
• 英文别名: 1-(125I)iodanyl-4-methoxybenzene
• CAS: 84211-78-9
• 化学式: C₇H₇IO
• 分子量: 232.132
• InChiKey: SYSZENVIJHPFNL-AAPUQBPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硼酸新戊二醇酯 在 sodium iodide 、 tetrakis(pyridine)copper(II) triflate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.17h， 生成 4-[¹²⁵I]-iodoanisole
  参考文献：
  名称：

  Rapid Cu-Catalyzed [²¹¹At]Astatination and [¹²⁵I]Iodination of Boronic Esters at Room Temperature

  摘要：

  Access to At-211- and I-125-radiolabeled compounds in excellent RCCs and RCYs was achieved in just 10 min at room temperature using a Cu catalyst. The reaction conditions are applicable to a broad class of aryl and heteroaryl boronic reagents with varying steric and electronic properties as well as late-stage astatination and iodination of anticancer PARP inhibitors. This protocol eliminates the traditional need for toxic organotin reagents, elevated temperatures, and extended reaction times, providing a more practical and environmentally friendly approach to developing a-emitting radiotherapeutics.

  DOI：

  10.1021/acs.orglett.8b00232

文献信息

• Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes
  作者：Stacey Webster、Kerry M. O'Rourke、Conor Fletcher、Sally L. Pimlott、Andrew Sutherland、Ai-Lan Lee

  DOI：10.1002/chem.201704534

  日期：2018.1.19

  Radiopharmaceuticals that incorporate radioactive iodine in combination with single-photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air- and moisture-stable

  将放射性碘与单光子发射计算机断层扫描成像相结合的放射性药物在核医学中起着关键作用，并在药物开发和疾病诊断中得到应用。尽管具有这种重要性，但是将放射性碘掺入小分子的通用方法相对较少。这项工作报告了一种快速的对空气和水分稳定的异丙基碘代硼烷化工艺，该工艺在无毒的绿色溶剂碳酸二甲酯中使用NIS。金催化方法的快速反应和温和条件导致了对芳烃进行放射性标记的高效方法的发展，这构成了将均相金催化应用于选择性放射性合成的第一个例子。
• Mechanism of Cu-Catalyzed Aryl Boronic Acid Halodeboronation Using Electrophilic Halogen: Development of a Base-Catalyzed Iododeboronation for Radiolabeling Applications
  作者：John J. Molloy、Kerry M. O’Rourke、Carolina P. Frias、Nikki L. Sloan、Matthew J. West、Sally L. Pimlott、Andrew Sutherland、Allan J. B. Watson

  DOI：10.1021/acs.orglett.9b00942

  日期：2019.4.5

  Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen reagents is reported. Evidence is provided to show that this takes place via a boronate-driven ipso-substitution pathway and that Cu is not required for these processes to operate: general Lewis base catalysis is operational. This in turn allows the rational development of a general, simple, and effective base-catalyzed halodeboronation

  报道了使用亲电子卤素试剂对铜催化的芳基硼酸卤代硼烷化反应机理的研究。提供的证据表明这是通过硼酸酯驱动的ipso取代途径发生的，并且这些过程的运行不需要Cu：一般的Lewis碱催化是可行的。这进而允许合理开发通用，简单且有效的碱催化卤代硼烷，该卤代硼烷适合制备125 I标记的SPECT应用产品。
• A hybrid solid-fluorous phase radioiodination and purification platform
  作者：James P. K. Dzandzi、Denis R. Beckford Vera、John F. Valliant

  DOI：10.1002/jlcr.3214

  日期：2014.7

  A new class of fluorous materials was developed to create a hybrid solid-solution phase strategy for the expedient preparation and HPLC-free purification of 125I-labeled compounds. The system is referred to as a hybrid platform in that it combines solution phase labeling and fluorous solid-phase purification in one step as opposed to two separate individual processes. Treatment of fluorous arylstannanes coated on fluorous silica with [125I]NaI and the appropriate oxidant made it possible to produce and selectively isolate the nonfluorous radiolabeled products in high purity (>98%) free from excess starting material and unreacted radioiodine. Examples included simple aryl and heterocyclic (click) derivatives, known radiopharmaceuticals including meta-iodobenzylguanidine (MIBG) and iododeoxyuridine (IUdR), and a new agent with high affinity for prostate-specific membrane antigen. The coated fluorous silica kits are simple to prepare, and reactions can be performed at room temperature using different oxidants generating products in minutes in biocompatible solutions.

  开发了一种新的氟聚合物材料，以创建一种混合固态-溶液相策略，使125I标记化合物的快速制备和无HPLC纯化成为可能。该系统被称为混合平台，因为它将溶液相标记和氟固相纯化结合在一步中，而不是两个单独的过程。用[125I]NaI和适当的氧化剂处理涂覆在氟硅氧烷上的氟芳基锡化合物，使得能够高纯度（>98%）地生产并选择性分离出无氟的放射性标记产物，且不含多余的起始材料和未反应的放射性碘。例子包括简单的芳香族和杂环（点击）衍生物，已知的放射药物包括美托碘苯基胍（MIBG）和碘脱氧尿苷（IUdR），以及一种对前列腺特异性膜抗原具有高亲和力的新试剂。涂覆的氟硅氧烷试剂盒易于制备，可以在室温下使用不同的氧化剂进行反应，在生物相容溶液中几分钟内生成产物。
• A one-pot radioiodination of aryl amines via stable diazonium salts: preparation of ¹²⁵I-imaging agents
  作者：Nikki L. Sloan、Sajinder K. Luthra、Graeme McRobbie、Sally L. Pimlott、Andrew Sutherland

  DOI：10.1039/c7cc06211g

  日期：——

  An operationally simple, one-pot, two-step tandem procedure that allows the incorporation of radioactive iodine into aryl amines via stable diazonium salts is described. The mild conditions are tolerant of various functional groups and substitution patterns, allowing late-stage, rapid access to a wide range of 125I-labelled aryl compounds and SPECT radiotracers.

  描述了一种操作简单，一锅，两步的串联程序，该程序允许将放射性碘通过稳定的重氮盐掺入芳基胺中。温和的条件可以耐受各种官能团和取代模式，从而可以后期快速地获得各种125 I标记的芳基化合物和SPECT放射性示踪剂。
• Unexpected Behavior of the Heaviest Halogen Astatine in the Nucleophilic Substitution of Aryliodonium Salts
  作者：François Guérard、Yong-Sok Lee、Kwamena Baidoo、Jean-François Gestin、Martin W. Brechbiel

  DOI：10.1002/chem.201600922

  日期：2016.8.22

  Aryliodonium salts have become precursors of choice for the synthesis of 18F‐labeled tracers for nuclear imaging. However, little is known on the reactivity of these compounds with heavy halides, that is, radioiodide and astatide, at the radiotracer scale. In the first comparative study of radiohalogenation of aryliodonium salts with 125I− and 211At−, initial experiments on a model compound highlight

  金盏花盐已成为合成18 F标记的核成像示踪剂的首选前体。然而，在放射性示踪剂规模上，这些化合物与重卤化物，即放射性碘化物和a化物的反应性知之甚少。与芳基碘鎓盐的放射性卤化的第一比较研究125我-和211在- ，上模型化合物最初的实验中突出砹的较高的反应性相比，碘化物，这不能从先前的卤素系列内观察到的趋势预料到的。动力学研究表明，活化能存在显着差异（E a = 23.5和17.1 kcal mol -1与125我-和211在- ，分别）。量子化学计算表明，stat化作用是通过碘鎓络合物的单体形式发生的，而碘化作用是通过异二聚碘鎓中间体发生的。用不同取代的芳基碘鎓盐实现的卤代区域选择性良好且产率高，这表明这类化合物是目前用于核医学示踪剂重放射性卤素标记的锡烷化学的有前途的替代品。