2-phenoxy-1-(2-pyridyl)ethanol | 115462-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-phenoxy-1-(2-pyridyl)ethanol
• 英文别名: (+/-)-2-Phenoxy-1-(2-pyridinyl)ethanol；2-Phenoxy-1-pyridin-2-ylethanol
• CAS: 115462-36-7
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: ZIDRQEMNHBSPOP-UHFFFAOYSA-N

物化性质

• 沸点：
  388.2±32.0 °C(predicted)
• 密度：
  1.181±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-phenoxy-1-(2-pyridyl)ethanol 在 platinum(IV) oxide 盐酸 、 氢氧化钾 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 erythro-1-(phenoxymethyl)-3,5,6,7,8,8a-hexahydro-1H-oxazolo<3,4-a>pyridine
  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-phenoxy-1-(2-pyridyl)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

• Asymmetric Catalysis; 138: Synthesis of Enantiomerically Pure 2-Pyridinyl-α-ethanols via Diastereomeric Camphanic Esters
  作者：Henri Brunner、Darijo Mijolović、Manfred Zabel

  DOI：10.1055/s-2001-16767

  日期：——

  The pure diastereomers were accessible by separating the diastereomeric esters with medium-pressure silica gel chromatography or fractional crystallization. X-ray structure analysis of the pure camphanic esters established the absolute configurations of the 2-pyridinyl-alcohols. The enantiomerically pure alcohols were obtained after saponification of the diastereomerically pure esters.

  Synthesis 2001, No. 11, 28 08 2001。文章标识符：1437-210X,E;2001,0,11,1671,1680,ftx,en;Z04601SS.pdf。© Georg Thieme Verlag Stuttgart · New York ISSN 0039-7881 摘要：制备了基于2-吡啶-乙醇骨架的新型三齿面结合配体作为外消旋体。与对映体纯的 (-)-(1S,4R)-樟脑酰氯反应得到非对映体樟脑酯。通过用中压硅胶色谱法或分级结晶分离非对映体酯，可获得纯的非对映体。纯樟脑酯的 X 射线结构分析确定了 2-吡啶醇的绝对构型。在非对映异构纯酯皂化后获得对映异构纯醇。
• 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.