1-{(R)-2-[(R)-1-Hydroxy-2-(naphthalen-2-yloxy)-ethyl]-piperidin-1-yl}-ethanone | 115462-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-{(R)-2-[(R)-1-Hydroxy-2-(naphthalen-2-yloxy)-ethyl]-piperidin-1-yl}-ethanone
• CAS: 115462-62-9
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: JTOMDEGJGDUHFN-MOPGFXCFSA-N

物化性质

• 沸点：
  534.8±20.0 °C(predicted)
• 密度：
  1.185±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-{(R)-2-[(R)-1-Hydroxy-2-(naphthalen-2-yloxy)-ethyl]-piperidin-1-yl}-ethanone 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 (1R)-2-naphthalen-2-yloxy-1-[(2R)-piperidin-2-yl]ethanol
  参考文献：
  名称：

  Synthesis and .beta.-adrenergic antagonism of 2-(aryloxy)-1-(2-piperidyl)ethanols

  摘要：

  A series of erythro- and threo-2-(aryloxy)-1-(2-piperidyl)ethanol derivatives (3) was synthesized from 2-(2-oxiranyl)pyridine for evaluation as beta-antagonists. Most compounds displayed high competitive beta-blocking potency, but they lacked significant beta 1/beta 2 selectivity. The 1-naphthoxy derivative erythro-3b was 17 (beta 1) and 33 (beta 2) times more potent than its open-chain analogue, propranolol. Within the whole series, erythro-3 diastereomers were more potent beta-blockers than the threo-3 isomers, and the potency of the latter seems to be rather insensitive to structural modification. The effect of N-methylation and of interposition of an alkyl chain between the aromatic ring and the side chain, while being detrimental to beta-blocking activity, was less marked than in the classic (aryloxy)propanolamine blockers.

  DOI：

  10.1021/jm00119a011
• 作为产物：
  描述：

  2-(Naphthalen-2-yloxy)-1-pyridin-2-yl-ethanol 在 platinum(IV) oxide 盐酸 、 sodium hydroxide 、 氢气 作用下， 以 氯仿 为溶剂， 生成 1-{(R)-2-[(R)-1-Hydroxy-2-(naphthalen-2-yloxy)-ethyl]-piperidin-1-yl}-ethanone
  参考文献：
  名称：

  Synthesis and .beta.-adrenergic antagonism of 2-(aryloxy)-1-(2-piperidyl)ethanols

  摘要：

  A series of erythro- and threo-2-(aryloxy)-1-(2-piperidyl)ethanol derivatives (3) was synthesized from 2-(2-oxiranyl)pyridine for evaluation as beta-antagonists. Most compounds displayed high competitive beta-blocking potency, but they lacked significant beta 1/beta 2 selectivity. The 1-naphthoxy derivative erythro-3b was 17 (beta 1) and 33 (beta 2) times more potent than its open-chain analogue, propranolol. Within the whole series, erythro-3 diastereomers were more potent beta-blockers than the threo-3 isomers, and the potency of the latter seems to be rather insensitive to structural modification. The effect of N-methylation and of interposition of an alkyl chain between the aromatic ring and the side chain, while being detrimental to beta-blocking activity, was less marked than in the classic (aryloxy)propanolamine blockers.

  DOI：

  10.1021/jm00119a011