(R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(R)-(+)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate | 81039-90-9

• 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: (R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(R)-(+)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate
• 英文别名: (R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(S)-(-)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate；(RS)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-(4-aminophenyl)-α-phenylacetate；(R)-(-)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-(4-aminophenyl)-α-phenylacetate
• CAS: 81039-90-9；88000-56-0；88000-57-1；88000-61-7；88000-62-8
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: YXPZJNBNONRNGF-ZQRQZVKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.79
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(R)-(+)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate 、 3-甲基哌啶 在 硫酸 、 sodium nitrite 作用下， 生成 (R)-(-)-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-<4-<2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl>pheny>-α-phenylacetate
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated derivatives of 1-azabicyclo[2.2.2]oct-3-yl .alpha.-hydroxy-.alpha.-(4-iodophenyl)-.alpha.-phenylacetate as potential radiopharmaceuticals

  摘要：

  Two derivatives of (RS)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (1a) and three partially resolved (R)- or (S)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetates labeled with no carrier added iodine-125 (1b, 18, and 19) and iodine-123 (1c and 18a) were synthesized by the Wallach triazene approach. We have found that this approach is necessary to obtain no carrier added labeling and gives far better results than the direct electrophilic iodination. The obtained yields were 7 to 18% when using iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-125 labeled compounds. Our preliminary distribution studies indicate that 1b localizes in the organs known to have a large concentration of muscarinic receptors and that this localization is due to binding to those receptors.

  DOI：

  10.1021/jm00368a009
• 作为产物：
  描述：

  4-硝基二苯甲酮 在 Pd-polyethylamine 盐酸 、 二环己烷并-18-冠醚-6 、 氢气 、 sodium 、 potassium carbonate 、 zinc(II) iodide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 241.0h， 生成 (R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(R)-(+)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated derivatives of 1-azabicyclo[2.2.2]oct-3-yl .alpha.-hydroxy-.alpha.-(4-iodophenyl)-.alpha.-phenylacetate as potential radiopharmaceuticals

  摘要：

  Two derivatives of (RS)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (1a) and three partially resolved (R)- or (S)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetates labeled with no carrier added iodine-125 (1b, 18, and 19) and iodine-123 (1c and 18a) were synthesized by the Wallach triazene approach. We have found that this approach is necessary to obtain no carrier added labeling and gives far better results than the direct electrophilic iodination. The obtained yields were 7 to 18% when using iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-125 labeled compounds. Our preliminary distribution studies indicate that 1b localizes in the organs known to have a large concentration of muscarinic receptors and that this localization is due to binding to those receptors.

  DOI：

  10.1021/jm00368a009