4-[¹²⁵I]iodonitrobenzene | 133622-64-7

• 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: 4-[¹²⁵I]iodonitrobenzene
• 英文别名: 1-¹²⁵Jod-4-nitrobenzol；1-[¹²⁵I]iodo-4-nitro-benzene；1-(125I)iodanyl-4-nitrobenzene
• CAS: 133622-64-7
• 化学式: C₆H₄INO₂
• 分子量: 247.103
• InChiKey: SCCCFNJTCDSLCY-SPNOHOMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-硝基苯胺 在 对甲苯磺酸 、 sodium iodide 作用下， 以 乙腈 、 水 为溶剂， 反应 2.25h， 以93%的产率得到4-[¹²⁵I]iodonitrobenzene
  参考文献：
  名称：

  通过稳定的重氮盐对芳基胺进行一锅放射性碘化：制备125 I成像剂

  摘要：

  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。

  DOI：

  10.1039/c7cc06211g

文献信息

• 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。
• Nickel-Mediated Radioiodination of Aryl and Heteroaryl Bromides: Rapid Synthesis of Tracers for SPECT Imaging
  作者：Alastair A. Cant、Sue Champion、Rajiv Bhalla、Sally L. Pimlott、Andrew Sutherland

  DOI：10.1002/anie.201302800

  日期：2013.7.22

  Rapid and efficient radioiodination of aryl and heteroaryl bromides has been achieved using a nickel(0)‐mediated halogen‐exchange reaction. This transformation gives direct access to [123I]‐ and [125I]‐imaging agents for single photon emission computed tomography (SPECT), such as 5‐[123I]‐A85380 (see scheme, Boc=tert‐butyloxycarbonyl, cod=1,5‐cyclooctadiene, TFA=trifluoroacetic acid).

  使用镍（0）介导的卤素交换反应已实现了芳基和杂芳基溴化物的快速有效碘化。此转换可直接访问用于单光子发射计算机断层扫描（SPECT）的[ 123 I]-和[ 125 I]-成像剂，例如5- [ 123 I] -A85380（请参阅方案，Boc =叔丁氧羰基，化学需氧量= 1,5-环辛二烯，TFA =三氟乙酸）。
• Rapid Cu-Catalyzed [²¹¹At]Astatination and [¹²⁵I]Iodination of Boronic Esters at Room Temperature
  作者：Sean W. Reilly、Mehran Makvandi、Kuiying Xu、Robert H. Mach

  DOI：10.1021/acs.orglett.8b00232

  日期：2018.4.6

  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.
• Komori, H.; Nishioka, K., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S945 - S947
  作者：Komori, H.、Nishioka, K.

  DOI：——

  日期：——
• [EN] METHOD FOR SYNTHESIZING IODO- OR ASTATOARYL COMPOUNDS USING ARYLSULFONIUM SALTS<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE COMPOSÉS IODO- OU ASTATOARYLE À L'AIDE DE SELS D'ARYLSULFONIUM
  申请人：[en]INSTITUT NATIONAL DE LA SANTÉ ET DE LA RECHERCHE MÉDICALE

  公开号：WO2023222909A1

  公开（公告）日：2023-11-23

  The inventors have now succeeded in developing arylsulfonium salts, in particular triarylsulfonium salts and dibenzothiophenium salts and a new use of said arylsulfonium salts. These compounds have the advantage of having a thioaryl group as leaving group, which allows all side products to be separated from the radiolabelled product. Said compounds are therefore useful tools in a method for synthesizing iodo- or astatoarryl compounds, in particular radioiodo- or radioastatoaryl compounds. The present invention relates to a method for synthesizing iodo- or astatoaryl compounds comprising the reaction of an arylsulfonium compound with an iodide or astatide salt, respectively. The invention also relates to arylsulfonium compounds as such. The invention also concerns a method of synthesizing an iodo- or astatolabelled biomolecule and/or vector using said iodo- or astatoraryl compound.