从一组常见起始原料出发的有机磷酸酯[C]VX和[C]沙林模拟物的发散合成。
Divergent synthesis of organophosphate [C]VX- and [C]Sarin-surrogates from a common set of starting materials.
作者信息
Hayes Thomas R, Blecha Joseph E, Thompson Charles M, Gerdes John M, VanBrocklin Henry F
机构信息
Department of Radiology and Biomedical Imaging, University of California - San Francisco, 185 Berry St. Suite 350, San Francisco, CA, 94107, United States.
Department of Biomedical and Pharmaceutical Sciences, University of Montana, Missoula, MT, 59812, United States.
出版信息
Appl Radiat Isot. 2019 Sep;151:182-186. doi: 10.1016/j.apradiso.2019.05.033. Epub 2019 May 24.
Abstract
Radiolabeled 1-[C]ethyl, 4-nitrophenyl methylphosphonate (VX surrogate) and 2-[C]-propanyl, 4-nitrophenyl methylphosphonate (sarin surrogate) were developed as organophosphate (OP) tracers. The [C]ethyl- and [C]isopropyl-iodide radiolabeled synthons were obtained by temperature controlled, in loop reactions of [C]CO with MeMgBr followed by reduction with LiAlH, then reaction with HI. Distillation of the [C]alkyl iodides into a solution of hydrogen (4-nitrophenyl)methylphosphonate and cesium carbonate afforded the desired tracers in >95% radiochemical purity, yields from [C]CO of 1-3% and 1.7-15.1 GBq/mmol molar activities.
摘要
放射性标记的1-[¹⁴C]乙基-4-硝基苯基甲基膦酸酯（VX替代物）和2-[¹⁴C]丙基-4-硝基苯基甲基膦酸酯（沙林替代物）被开发用作有机磷酸酯（OP）示踪剂。[¹⁴C]乙基-和[¹⁴C]异丙基-碘放射性标记的合成子是通过在[¹⁴C]CO与MeMgBr的循环反应中控制温度获得的，随后用LiAlH₄还原，然后与HI反应。将[¹⁴C]烷基碘蒸馏到氢（4-硝基苯基）甲基膦酸酯和碳酸铯的溶液中，得到所需的示踪剂，其放射化学纯度>95%，以[¹⁴C]CO计的产率为1-3%，摩尔活度为1.7-15.1 GBq/mmol。
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