2-(Naphthalen-2-yloxy)-1-pyridin-2-yl-ethanol | 115462-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(Naphthalen-2-yloxy)-1-pyridin-2-yl-ethanol
• 英文别名: 2-Naphthalen-2-yloxy-1-pyridin-2-ylethanol
• CAS: 115462-37-8
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: SBHURJVSGXFWHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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-[(2R)-2-[(1S)-1-hydroxy-2-naphthalen-2-yloxyethyl]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
• 作为产物：
  描述：

  2-乙烯基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(Naphthalen-2-yloxy)-1-pyridin-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