3-(2-nitroimidazolyl)-1-(2-chloro-2,2-difluoroethoxy)-propane-2-ol | 1300731-34-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-(2-nitroimidazolyl)-1-(2-chloro-2,2-difluoroethoxy)-propane-2-ol
• CAS: 1300731-34-3
• 化学式: C₈H₁₀ClF₂N₃O₄
• 分子量: 285.635
• InChiKey: LNPUULGTLHLHGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  90.42
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(2-nitroimidazolyl)-1-(2-chloro-2,2-difluoroethoxy)-propane-2-ol 在 盐酸 、 Kryptofix222[18F]钾盐 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 生成 1-((2,2-difluorovinyl)oxy)-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol
  参考文献：
  名称：

  Radiosynthesis of the tumor hypoxia marker [18F]TFMISO via O-[18F]trifluoroethylation reveals a striking difference between trifluoroethyl tosylate and iodide in regiochemical reactivity toward oxygen nucleophiles

  摘要：

  The MRI hypoxia marker trifluoromisonidazole (TFMISO) [1-(2-nitro-1H-imidazol-1-yl)-3-(2,2,2-trifluoroethoxy) propan-2-ol] was successfully labeled with F-18 to expand its role into a bimodal PET/MRI probe. F-18-Labeling was achieved via a three-step procedure in which 2,2,2-[F-18]trifluoroethyl p-toluenesulfonate prepared by F-18-F-19 exchange served as the [F-18]trifluoroethylating agent. The O-[F-18]trifluoroethylation reaction proceeded efficiently to give the intermediate 1,2-epoxy-3-(2,2,2-[F-18]trifluoroethoxy) propane, with approximately 60% of F-18 incorporated from the tosylate precursor, which was condensed with 2-nitroimidazole to yield [F-18] TFMISO. Approximately 40% of the [F-18] trifluoroethyl tosylate precursor was converted into the final product. In stark contrast, 2,2,2-[F-18] trifluoroethyl iodide failed to produce [F-18] TFMISO, giving instead 1,1-[F-18]difluoro-2-iodoethoxy and 1-[F-18]fluoro-2-iodovinyloxy analogs of [F-18] TFMISO. Thus, this investigation has identified 2,2,2-[F-18] trifluoroethyl tosylate as an excellent [F-18] trifluoroethylating agent, which can convert efficiently an alcohol into the corresponding [F-18] trifluoroethyl ether. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.02.026
• 作为产物：
  描述：

  2-硝基咪唑 、 2-epoxy-3-(2-chloro-2,2-difluoroethoxy)propane 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 3-(2-nitroimidazolyl)-1-(2-chloro-2,2-difluoroethoxy)-propane-2-ol
  参考文献：
  名称：

  Radiosynthesis of the tumor hypoxia marker [18F]TFMISO via O-[18F]trifluoroethylation reveals a striking difference between trifluoroethyl tosylate and iodide in regiochemical reactivity toward oxygen nucleophiles

  摘要：

  The MRI hypoxia marker trifluoromisonidazole (TFMISO) [1-(2-nitro-1H-imidazol-1-yl)-3-(2,2,2-trifluoroethoxy) propan-2-ol] was successfully labeled with F-18 to expand its role into a bimodal PET/MRI probe. F-18-Labeling was achieved via a three-step procedure in which 2,2,2-[F-18]trifluoroethyl p-toluenesulfonate prepared by F-18-F-19 exchange served as the [F-18]trifluoroethylating agent. The O-[F-18]trifluoroethylation reaction proceeded efficiently to give the intermediate 1,2-epoxy-3-(2,2,2-[F-18]trifluoroethoxy) propane, with approximately 60% of F-18 incorporated from the tosylate precursor, which was condensed with 2-nitroimidazole to yield [F-18] TFMISO. Approximately 40% of the [F-18] trifluoroethyl tosylate precursor was converted into the final product. In stark contrast, 2,2,2-[F-18] trifluoroethyl iodide failed to produce [F-18] TFMISO, giving instead 1,1-[F-18]difluoro-2-iodoethoxy and 1-[F-18]fluoro-2-iodovinyloxy analogs of [F-18] TFMISO. Thus, this investigation has identified 2,2,2-[F-18] trifluoroethyl tosylate as an excellent [F-18] trifluoroethylating agent, which can convert efficiently an alcohol into the corresponding [F-18] trifluoroethyl ether. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.02.026