1-(4-benzyloxy)phenyl-2-(4-hydroxy-4-phenyl)piperidin-1-yl-ethan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-benzyloxy)phenyl-2-(4-hydroxy-4-phenyl)piperidin-1-yl-ethan-1-one
• 英文别名: 2-(4-Hydroxy-4-phenylpiperidin-1-yl)-1-(4-phenylmethoxyphenyl)ethanone
• 化学式: C₂₆H₂₇NO₃
• 分子量: 401.505
• InChiKey: AKESRJHWQLUELJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  碘化甲烷-14C 、 1-(4-benzyloxy)phenyl-2-(4-hydroxy-4-phenyl)piperidin-1-yl-ethan-1-one 在 sodium hexamethyldisilazane 作用下， 生成 1-(4-benzyloxy)phenyl-2-(4-hydroxy-4-phenyl)piperidin-1-yl-[3-14C]propan-1-one
  参考文献：
  名称：

  Synthesis of high-specific activity tritium and optically pure [14C]CP-101,606. Enantioselective crystallization of a radiochemically racemic mixture

  摘要：

  The syntheses of racemic, high-specific activity tritium and optically pure, carbon-14 labelled CP-101,606 is described. The tritium labelled material was prepared at 35.6 Ci/mmol by hydrogenolysis of the dibromo analog (5) under bar. In the carbon-14 synthesis, the radiolabel was introduced in the final carbon-carbon bond forming step by alkylation of the readily available aminoketone (8) under bar with [C-14]methyl iodide. Three-selective sodium borohydride reduction of the ketone and deprotection of the phenol gave racemic [C-14]CP-101,606. Enantiomerically pure (+)-[C-14]CP-101,606 was obtained by addition of optically pure, unlabelled drug and directly recrystallizing the enantiomerically enriched, but radiochemically racemic, mixture.

  DOI：

  10.1002/(sici)1099-1344(199712)39:12<973::aid-jlcr40>3.0.co;2-o
• 作为产物：
  描述：

  4-苯甲氧基苯乙酮 在 三乙胺 、 copper(ll) bromide 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 反应 6.5h， 生成 1-(4-benzyloxy)phenyl-2-(4-hydroxy-4-phenyl)piperidin-1-yl-ethan-1-one
  参考文献：
  名称：

  Synthesis of high-specific activity tritium and optically pure [14C]CP-101,606. Enantioselective crystallization of a radiochemically racemic mixture

  摘要：

  The syntheses of racemic, high-specific activity tritium and optically pure, carbon-14 labelled CP-101,606 is described. The tritium labelled material was prepared at 35.6 Ci/mmol by hydrogenolysis of the dibromo analog (5) under bar. In the carbon-14 synthesis, the radiolabel was introduced in the final carbon-carbon bond forming step by alkylation of the readily available aminoketone (8) under bar with [C-14]methyl iodide. Three-selective sodium borohydride reduction of the ketone and deprotection of the phenol gave racemic [C-14]CP-101,606. Enantiomerically pure (+)-[C-14]CP-101,606 was obtained by addition of optically pure, unlabelled drug and directly recrystallizing the enantiomerically enriched, but radiochemically racemic, mixture.

  DOI：

  10.1002/(sici)1099-1344(199712)39:12<973::aid-jlcr40>3.0.co;2-o