C-4-[18F]fluorophenyl-N-phenyl nitrone | 1355486-25-7

• 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: C-4-[18F]fluorophenyl-N-phenyl nitrone
• 英文别名: C-4-[¹⁸F]fluorophenyl-N-phenyl nitrone
• CAS: 1355486-25-7
• 化学式: C₁₃H₁₀FNO
• 分子量: 214.228
• InChiKey: GJTOMWKYUWVHDO-UMSOTBISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  C-4-[18F]fluorophenyl-N-phenyl nitrone 、 1-(丙-2-炔-1-基)嘧啶-2,4(1H,3H)-二酮 在 吡啶 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以60%的产率得到
  参考文献：
  名称：

  Synthesis of¹⁸F-Labelled β-Lactams by Using the Kinugasa Reaction

  摘要：

  AbstractOwing to their broad spectrum of biological activities and low toxicity, β‐lactams are attractive lead structures for the design of novel molecular probes. However, the synthesis of positron emission tomography (PET)‐isotope‐labelled β‐lactams has not yet been reported. Herein, we describe the simple preparation of radiofluorinated β‐lactams by using the fast Kinugasa reaction between 18F‐labelled nitrone [18F]‐1 and alkynes of different reactivity. Additionally, 18F‐labelled fused β‐lactams were obtained through the reaction of a cyclic nitrone 7 with radiofluorinated alkynes [18F]‐6 a,b. Radiochemical yields of the Kinugasa reaction products could be significantly increased by the use of different CuI ligands, which additionally allowed a reduction in the amount of precursor and/or reaction time. Model radiofluorinated β‐lactam‐peptide and protein conjugates ([18F]‐10 and 18F‐labelled BSA conjugate) were efficiently obtained in high yield under mild conditions (aq. MeCN, ambient temperature) within a short reaction time, demonstrating the suitability of the developed method for radiolabelling of sensitive molecules such as biopolymers.

  DOI：

  10.1002/chem.201304056
• 作为产物：
  描述：

  4-trimethylammoniumbenzaldehyde triflate 在 盐酸 、 [¹⁸F]fluoride 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 乙醇 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 0.34h， 生成 C-4-[18F]fluorophenyl-N-phenyl nitrone
  参考文献：
  名称：

  Synthesis of¹⁸F-Labelled β-Lactams by Using the Kinugasa Reaction

  摘要：

  AbstractOwing to their broad spectrum of biological activities and low toxicity, β‐lactams are attractive lead structures for the design of novel molecular probes. However, the synthesis of positron emission tomography (PET)‐isotope‐labelled β‐lactams has not yet been reported. Herein, we describe the simple preparation of radiofluorinated β‐lactams by using the fast Kinugasa reaction between 18F‐labelled nitrone [18F]‐1 and alkynes of different reactivity. Additionally, 18F‐labelled fused β‐lactams were obtained through the reaction of a cyclic nitrone 7 with radiofluorinated alkynes [18F]‐6 a,b. Radiochemical yields of the Kinugasa reaction products could be significantly increased by the use of different CuI ligands, which additionally allowed a reduction in the amount of precursor and/or reaction time. Model radiofluorinated β‐lactam‐peptide and protein conjugates ([18F]‐10 and 18F‐labelled BSA conjugate) were efficiently obtained in high yield under mild conditions (aq. MeCN, ambient temperature) within a short reaction time, demonstrating the suitability of the developed method for radiolabelling of sensitive molecules such as biopolymers.

  DOI：

  10.1002/chem.201304056