2-[¹²⁵I]iodo-benzoic acid | 58861-27-1

• 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: 2-[¹²⁵I]iodo-benzoic acid
• 英文别名: 2-(125I)iodanylbenzoic acid
• CAS: 58861-27-1
• 化学式: C₇H₅IO₂
• 分子量: 246.115
• InChiKey: CJNZAXGUTKBIHP-AAPUQBPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  sodium benzoate 在 palladium dichloride 、 1-(125I)iodanylpyrrolidine-2,5-dione 、 三氟乙酸 作用下， 以 氘代乙腈 为溶剂， 反应 24.25h， 生成 2-[¹²⁵I]iodo-benzoic acid
  参考文献：
  名称：

  Palladium-Mediated Site-Selective C–H Radio-iodination

  摘要：

  The palladium-mediated C-H radio-iodination of arenes using sodium iodide as the primary isotopic source is reported and performed without chemical know-how in 30 min and applied to the synthesis of complex radio-iodinated compounds of biological interest.

  DOI：

  10.1021/acs.orglett.8b02819

文献信息

• Copper‐mediated radioiodination reaction through aryl boronic acid or ester precursor and its application to direct radiolabeling of a cyclic peptide
  作者：Yuto Kondo、Hiroyuki Kimura、Chiaki Fukumoto、Yusuke Yagi、Yasunao Hattori、Hidekazu Kawashima、Hiroyuki Yasui

  DOI：10.1002/jlcr.3925

  日期：2021.6.30

  A copper-mediated radioiodination using aryl boronic precursors is attracting attention as a solution to oxidative iododestannylation and nickel-mediated radioiodination drawbacks. The copper-mediated radiolabeling method allows radioiodination at room temperature with stable aryl boronic precursors without preparing complex starting materials or reagents and can be performed in a reaction vessel exposed to air. This method has good potential in radiochemistry; however, studies on the scope of copper-mediated radioiodination through boronic precursors are insufficient. In particular, few reports have demonstrated the effect of protecting groups on radiolabeling efficiency. Therefore, the effect of the protecting group of aryl boronic acids on the copper-mediated radioiodination was investigated. In addition, this method, which does not require heating, is expected to be useful for direct radiolabeling of peptides. Thus, we attempted direct radioiodination of c(RGDyk) as an example. The resulting radioiodination method was well tolerated in various substrates and was unaffected by the pinacol ester-type protecting group. Also, c(RGDyk) was labeled with 125I via copper-mediated radioiodination using an aryl boronic acid precursor. The reaction time and yield were improved, compared with the indirect method. Furthermore, the large difference in polarity between the boronic acid precursor and the radiolabeled compound facilitated purification.

  铜介导的使用芳基硼酸前体的放射性碘化法作为解决氧化碘锡化和镍介导的放射性碘化法缺点的一种方法，正在引起人们的关注。铜介导的放射标记法可以在室温下使用稳定的芳基硼酸前体进行放射碘化，无需准备复杂的起始材料或试剂，而且可以在暴露于空气中的反应容器中进行。这种方法在放射化学领域具有很好的应用前景；然而，有关铜通过硼酸前体介导的放射性碘化范围的研究还不够充分。特别是，很少有报告证明保护基团对放射性标记效率的影响。因此，我们研究了芳基硼酸的保护基团对铜介导的放射碘化的影响。此外，这种无需加热的方法有望用于多肽的直接放射性标记。因此，我们以 c(RGDyk)为例尝试了直接放射性碘化。在各种底物中，放射性碘化方法的耐受性都很好，而且不受频哪醇酯类保护基的影响。此外，还利用芳基硼酸前体，通过铜介导的放射碘化法用 125I 标记了 c(RGDyk)。与间接法相比，反应时间和收率都有所提高。此外，硼酸前体和放射性标记化合物之间的极性差异较大，有利于纯化。