α-phenoxymethyl-2-piperidinemethanol | 117575-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: α-phenoxymethyl-2-piperidinemethanol
• 英文别名: 2-Phenoxy-1-piperidin-2-ylethanol
• CAS: 117575-36-7
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: XYXMJNFELPKDTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-phenoxymethyl-2-piperidinemethanol 在 氢氧化钾 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 7.0h， 生成 threo-2-phenoxy-1-(2-piperidyl)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-乙烯基吡啶 在 platinum(IV) oxide 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 氢气 、 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 α-phenoxymethyl-2-piperidinemethanol
  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

• Syntheis of 2-aryloxy- and 2-arylalkoxy-1-(2-piperidyl)ethanols
  作者：David Mauleón、M. Dolors Pujol、Cristina Minguillón、Jaume Miquel

  DOI：10.1002/jhet.5570260331

  日期：1989.5

  The preparation and separation of diastereomeric pairs of a series of 2-aryloxy- and 2-arylalkoxy-1-(2-piperidyl)ethanols is reported. The erythro aminoalcohols were converted into threo isomers by thionyl chloride treatment of their N-acetyl derivatives and alkaline hydrolysis.

  报道了一系列2-芳氧基-和2-芳基烷氧基-1-（2-哌啶基）乙醇的非对映体对的制备和分离。通过亚硫酰氯的N-乙酰基衍生物的亚硫酰氯处理和碱水解，将赤型氨基醇转化为苏式异构体。
• Aryloxymethyl derivatives of nitrogenous heterocyclic methanols and ethers thereof having cardiovascular activity
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0279707A2

  公开（公告）日：1988-08-24

  Novel heterocyclicmethanols are disclosed having the formula: wherein Z is pyrrolidinyl, piperidinyl, homopiperidinyl or pyridinyl;     R¹ is hydrogen, loweralkyl or carbethoxymethyl;     R² is hydrogen, loweralkyl or cycloalkyl, phenyl or phenyl-loweralkyl;     R³ is 1 or 2-naphthalenyl, 2,3-dihydroinden-4 or 5-yl, phenyl or phenyl substituted by loweralkyl, loweralkoxy, halogen, trifluoromethyl, phenyl, methylenedioxy, nitro, amino, loweralkylamino, diloweralkylamino, loweracylamino;     the 1-position of 2-pyrrolidinyl, 2-piperidinyl or 2-homopiperidinyl may be substituted by an R⁴ loweralkyl group, or R¹ may form methylene or -CH₂-C(O)- bridges with R⁴;     the pharmaceutically acceptable salts and diastereomers thereof, which compounds have antiarrhythmic and/or hypotensive activity in animals.

  公开了具有以下式子的新型杂环甲醇： 其中 Z 是吡咯烷基、哌啶基、均哌啶基或吡啶基； R¹ 是氢、低级烷基或碳氧甲基； R² 是氢、低级烷基或环烷基、苯基或苯基-低级烷基； R³ 是 1 或 2-萘基、2,3-二氢茚-4 或 5-基、苯基或被低级烷基、低级烷氧基、卤素、三氟甲基、苯基、亚甲基二氧基、硝基、氨基、低级烷基氨基、稀释低级烷基氨基、低级酰基氨基取代的苯基； 2-吡咯烷基、2-哌啶基或 2-高哌啶基的 1-位可被 R⁴ 低烷基取代，或 R¹ 可与 R⁴ 形成亚甲基或-CH₂-C(O)-桥； 其药学上可接受的盐和非对映异构体，这些化合物在动物体内具有抗心律失常和/或降血压活性。
• SHANKLIN, JAMES (JR);CHRISTOPHER, P. (III)
  作者：SHANKLIN, JAMES (JR)、CHRISTOPHER, P. (III)

  DOI：——

  日期：——
• US4835164A
  申请人：——

  公开号：US4835164A

  公开（公告）日：1989-05-30
• 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.