(1S)-2-(3-phenylpropoxy)-1-[(2S)-piperidin-2-yl]ethanol | 115462-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1S)-2-(3-phenylpropoxy)-1-[(2S)-piperidin-2-yl]ethanol
• CAS: 115462-52-7
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: PAWPHGFYSPEYBZ-JKSUJKDBSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  413.4±30.0 °C(predicted)
• 密度：
  1.044±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-乙烯基吡啶 在 platinum(IV) oxide 盐酸 、 氢氧化钾 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 氢气 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 12.0h， 生成 (1S)-2-(3-phenylpropoxy)-1-[(2S)-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

文献信息

• Synthesis and .beta.-adrenergic antagonism of 2-(aryloxy)-1-(2-piperidyl)ethanols
  作者：David Mauleon、Maria Dolors Pujol、Gloria Rosell

  DOI：10.1021/jm00119a011

  日期：1988.11

  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.