1-(1-fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol | 1044739-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(1-fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol
• 英文别名: (2S)-1-(1-fluoropropan-2-ylamino)-3-(3-methylphenoxy)propan-2-ol
• CAS: 1044739-90-3
• 化学式: C₁₃H₂₀FNO₂
• 分子量: 241.306
• InChiKey: DIYDLIFSZIZBCW-KIYNQFGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 palladium dihydroxide 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 生成 1-(1-fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol
  参考文献：
  名称：

  Facile Radiosynthesis of Fluorine-18 Labeled β-Blockers. Synthesis, Radiolabeling, and ex Vivo Biodistribution of [¹⁸F]-(2S and 2R)-1-(1-Fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol

  摘要：

  An efficient and genral method has been developed for fluorine-18 labeling of beta-blockers that possess the propanolamine moiety. A new synthetically versatile intermediate, 3-(1-(benzyloxy)propan-2-yl)-2-oxoox-azolidin-5-yl)methyl 4-methylbenzenesulfonate (13), was prepared and can be conjugated to any phenoxy core. To demonstrate the synthetic methodology, fluorinated derivatives of toliprolol were prepared, namely, [(18)F]-(2S and 2R)-]-(1-fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol ((2S and 2R)-[(18)F]1). The radiosyntheses were accomplished in < 1 h, with 20-24% (uncorrected for decay, n = 7) radiochemical yields, > 96% radiochemical and > 99% enantiomeric purities, with specific activities of 0.9-1.1 Ci/mu mol(EOS). Ex vivo biodistribution studies with the radiotracers demonstrated excessively rapid washout that May limit their use for cerebral PET imaging.

  DOI：

  10.1021/jm800227h

文献信息

• Facile Radiosynthesis of Fluorine-18 Labeled β-Blockers. Synthesis, Radiolabeling, and ex Vivo Biodistribution of [¹⁸F]-(2<i>S</i> and 2<i>R</i>)-1-(1-Fluoropropan-2-ylamino)-3-(<i>m</i>-tolyloxy)propan-2-ol
  作者：Karin A. Stephenson、Alan A. Wilson、Jeffrey H. Meyer、Sylvain Houle、Neil Vasdev

  DOI：10.1021/jm800227h

  日期：2008.8.1

  An efficient and genral method has been developed for fluorine-18 labeling of beta-blockers that possess the propanolamine moiety. A new synthetically versatile intermediate, 3-(1-(benzyloxy)propan-2-yl)-2-oxoox-azolidin-5-yl)methyl 4-methylbenzenesulfonate (13), was prepared and can be conjugated to any phenoxy core. To demonstrate the synthetic methodology, fluorinated derivatives of toliprolol were prepared, namely, [(18)F]-(2S and 2R)-]-(1-fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol ((2S and 2R)-[(18)F]1). The radiosyntheses were accomplished in < 1 h, with 20-24% (uncorrected for decay, n = 7) radiochemical yields, > 96% radiochemical and > 99% enantiomeric purities, with specific activities of 0.9-1.1 Ci/mu mol(EOS). Ex vivo biodistribution studies with the radiotracers demonstrated excessively rapid washout that May limit their use for cerebral PET imaging.