1-[2-(3-羟基苯基)乙基]哌啶 | 118511-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[2-(3-羟基苯基)乙基]哌啶
• 英文名称: 1-[2-(3-hydroxyphenyl)ethyl]piperidine
• 英文别名: 3-(2-(piperidin-1-yl)ethyl)phenol；3-(2-Piperidin-1-ylethyl)phenol
• CAS: 118511-59-4
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: QWDQHVUWPVBYHO-UHFFFAOYSA-N

物化性质

• 沸点：
  331.6±17.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二乙基氯甲酰胺 、 1-[2-(3-羟基苯基)乙基]哌啶 在 吡啶 、 三乙胺 作用下， 以58%的产率得到1-[2-(3-diethylcarbamoyloxyphenyl)ethyl]piperidine
  参考文献：
  名称：

  Synthesis and cholinesterase activity of phenylcarbamates related to Rivastigmine, a therapeutic agent for Alzheimer's disease

  摘要：

  In order to develop new cholinesterase agents effective against Alzheimer's disease (AD) we synthesized some phenylcarbamates structurally related to Rivastigmine and evaluated their in vitro and in vivo biological activity. Among the compounds which displayed the most significant in vitro activity, 1-[1-(3-dimethylcarbamoyloxyphenyl)ethyl]piperidine (31b), in addition to a simple and cheaper synthesis, showed lower toxicity and very similar therapeutic index in comparison with Rivastigmine. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(01)01324-1
• 作为产物：
  描述：

  3-甲氧基苯基乙酰氯 在 lithium aluminium tetrahydride 、 氢溴酸 作用下， 以 乙醚 、 水 为溶剂， 反应 9.0h， 生成 1-[2-(3-羟基苯基)乙基]哌啶
  参考文献：
  名称：

  Synthesis and cholinesterase activity of phenylcarbamates related to Rivastigmine, a therapeutic agent for Alzheimer's disease

  摘要：

  In order to develop new cholinesterase agents effective against Alzheimer's disease (AD) we synthesized some phenylcarbamates structurally related to Rivastigmine and evaluated their in vitro and in vivo biological activity. Among the compounds which displayed the most significant in vitro activity, 1-[1-(3-dimethylcarbamoyloxyphenyl)ethyl]piperidine (31b), in addition to a simple and cheaper synthesis, showed lower toxicity and very similar therapeutic index in comparison with Rivastigmine. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(01)01324-1

文献信息

• Phenoxymethyl piperidine derivatives being sodium channle blockers
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0869119A1

  公开（公告）日：1998-10-07

  The present invention relates to phenoxymethyl piperidine derivatives, and pharmaceutically acceptable salts and N-oxides thereof, which are sodium channel blockers, and thus exhibit useful pharmacological properties, including utility for the treatment of neuropathic pain conditions. represented by formula I: where: R1 is hydrogen, (C1-4)alkyl, -(CH2)mcycloalkyl, -(CH2)mNR7R8, or -(CH2)mNR7SO2R9; m is 1 to 3; R7 and R8 are independently hydrogen or (C1-4)alkyl; and R9 is (C1-4)alkyl; R2,R3,R5, and R6 are independently hydrogen, (C1-4)alkyl, or halogen; R4 is hydrogen, (C1-4)alkyl, hydroxy, alkyloxy, fluoroalkyloxy, halogen, or phenyl or mono- or di-substituted phenyl, the substituents selected from alkyloxy, amino, nitro or acetylamino; provided that when R1 is hydrogen at least two of R2,R3,R4,R5, and R6 are other than hydrogen; and further provided that when R1 is methyl and R2,R3,R5 and R6 are hydrogen, R4 is other than fluoro; or a pharmaceutically acceptable salt or N-oxide thereof, as an individual isomer or as a racemic or non-racemic mixture of isomers.

  本发明涉及苯氧基甲基哌啶衍生物及其药学上可接受的盐和 N-氧化物，它们是钠通道阻滞剂，因此具有有用的药理特性，包括用于治疗神经性疼痛病症。 由式 I 表示： 其中 R1 是氢、(C1-4)烷基、-(CH2)m 环烷基、-(CH2)mNR7R8 或-(CH2)mNR7SO2R9； m 为 1 至 3； R7 和 R8 独立地为氢或 (C1-4)烷基；以及 R9 是 (C1-4)烷基； R2、R3、R5 和 R6 独立地是氢、(C1-4)烷基或卤素； R4 是氢、(C1-4)烷基、羟基、烷氧基、氟烷氧基、卤素或苯基或单取代或二取代苯基，取代基选自烷氧基、氨基、硝基或乙酰氨基； 当 R1 为氢时，R2、R3、R4、R5 和 R6 中至少有两个不是氢；当 R1 为甲基，R2、R3、R5 和 R6 为氢时，R4 不是氟； 或其药学上可接受的盐或 N-氧化物，作为单个异构体或作为异构体的外消旋或非外消旋混合物。
• 2-Phenoxy-indan-1-one derivatives as acetylcholinesterase inhibitors: A study on the importance of modifications at the side chain on the activity
  作者：Yanhong Shen、Rong Sheng、Jing Zhang、Qiaojun He、Bo Yang、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.07.014

  日期：2008.8

  As a part of our project aimed at developing new agents of potential application in AD, a new series of 2-phenoxy-indan-1-one derivatives which possess alkylamine side chain were designed, synthesized and evaluated for their inhibitory activity against AChE and BuChE. Most of the compounds were found to inhibit AChE in the nanomolar range. The optimum inhibitor 3g exhibited 34-fold increase in AChE inhibition than donepezil and displayed neuroprotective effect against H2O2-induced cell death. (C) 2008 Elsevier Ltd. All rights reserved.
• TAMURA, TOSIYA;TSUKAMOTO, SINITI;USUDA, SINDZI;XARADA, MASATOMI
  作者：TAMURA, TOSIYA、TSUKAMOTO, SINITI、USUDA, SINDZI、XARADA, MASATOMI

  DOI：——

  日期：——
• US6110937A
  申请人：——

  公开号：US6110937A

  公开（公告）日：2000-08-29
• US6262078B1
  申请人：——

  公开号：US6262078B1

  公开（公告）日：2001-07-17