2-Propanol, 1-(2,3-diaminophenoxy)-3-[(1,1-dimethylethyl)amino]-, (R)- | 142204-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Propanol, 1-(2,3-diaminophenoxy)-3-[(1,1-dimethylethyl)amino]-, (R)-
• 英文别名: S-<1-(2,3-diaminophenoxy)>-3'-(N-t-butylamino)propan-2'-ol
• CAS: 142204-75-9
• 化学式: C₁₃H₂₃N₃O₂
• 分子量: 253.345
• InChiKey: UUEZBYYEYMGFRR-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  93.53
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-氨基-3-硝基苯酚 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 39.0h， 生成 2-Propanol, 1-(2,3-diaminophenoxy)-3-[(1,1-dimethylethyl)amino]-, (R)-
  参考文献：
  名称：

  S-[1-(2,3-diaminophenoxy)]-3′-(N-t-butylamino)propan-2′-ol-simplified asymmetric synthesis with CD and chiral HPLC analysis

  摘要：

  S-[1-(2,3-Diaminophenoxy)]-3'-(N-t-butylamino)propan-2'-ol is important as a precursor in the radiosynthesis of a C-11-labelled radioligand (S-[carbonyl-C-11]CGP 12177) for the study of beta-receptors in living man. The asymmetric synthesis of this precursor has been simplified based on the reaction of readily available 2-amino-3-nitrophenol and the chiral auxiliary, S-glycidyl-3-nitrobenzenesulphonate, followed by treatment of the resultant S-epoxide with t-butylamine and reduction with hydrogen in the presence of palladium on carbon. Chiral HPLC methods have been successfully developed to monitor the enantiomeric purity of the chiral auxiliary and of all intermediates in the asymmetric synthesis. All intermediates and products have been studied by CD. It has been demonstrated by chiral HPLC that S-CGP 12177 can be prepared in > 98.4% e.e. from the synthesised S-precursor. R-CGP 12177 (e.e. > 96.2%) was prepared analogously.

  DOI：

  10.1016/s0957-4166(00)80261-x

文献信息

• S-[1-(2,3-diaminophenoxy)]-3′-(N-t-butylamino)propan-2′-ol-simplified asymmetric synthesis with CD and chiral HPLC analysis
  作者：Franklin Aigbirhio、Victor W. Pike、Eric Francotte、Stephen L. Waters、Beaulah Banfield、Knut A. Jaeggi、Alex Drake

  DOI：10.1016/s0957-4166(00)80261-x

  日期：1992.4

  S-[1-(2,3-Diaminophenoxy)]-3'-(N-t-butylamino)propan-2'-ol is important as a precursor in the radiosynthesis of a C-11-labelled radioligand (S-[carbonyl-C-11]CGP 12177) for the study of beta-receptors in living man. The asymmetric synthesis of this precursor has been simplified based on the reaction of readily available 2-amino-3-nitrophenol and the chiral auxiliary, S-glycidyl-3-nitrobenzenesulphonate, followed by treatment of the resultant S-epoxide with t-butylamine and reduction with hydrogen in the presence of palladium on carbon. Chiral HPLC methods have been successfully developed to monitor the enantiomeric purity of the chiral auxiliary and of all intermediates in the asymmetric synthesis. All intermediates and products have been studied by CD. It has been demonstrated by chiral HPLC that S-CGP 12177 can be prepared in > 98.4% e.e. from the synthesised S-precursor. R-CGP 12177 (e.e. > 96.2%) was prepared analogously.