1-乙氧羰基-4-(2-甲苯基)哌啶-4-醇 | 96122-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-乙氧羰基-4-(2-甲苯基)哌啶-4-醇
• 英文名称: 1-ethoxycarbonyl-4-(2-tolyl)piperidin-4-ol
• 英文别名: ethyl 4-hydroxy-4-(2-methylphenyl)piperidine-1-carboxylate
• CAS: 96122-89-3
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: XKUMOJKOEZJWDU-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C(Solv: hexane (110-54-3); ethanol (64-17-5))
• 沸点：
  402.2±45.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙氧羰基-4-(2-甲苯基)哌啶-4-醇 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以49%的产率得到4-(2-甲基苯基)哌啶-4-醇
  参考文献：
  名称：

  Potential antiparkinsonic agents: Synthesis and pharmacology of some 4-fluoro-4'-halogen'benzhydryl 2-(N,N-disubstituted amino)ethyl ethers

  摘要：

  4,4'-二卤代苯基甲醇和1,1-二苯基乙醇Xab和XIab与氢氧化钠和2-二甲氨基乙基氯化物以及2-吡咯烷基乙基氯化物的反应产生了醚类化合物Vab-VIIIab。从苯基甲醇Xab和2-溴乙醇在硫酸的处理下得到2-溴乙基醚类化合物IXab，随后将其进行取代反应，反应物为4-苯基哌啶-4-醇、4-(2-甲苯基)哌啶-4-醇（XVI）、4-(4-氟苯基)哌啶-4-醇和4-(2-氧代苯并咪唑啉-1-基)哌啶（XVII），产生了氨基醚类化合物XIIab-XIVab和XIXab。这些产物被评估为潜在的抗帕金森病药物，并与flunamine（III）进行比较。醚类化合物Va、Vb和VIa显示了与flunamine（III）相似的抗痉挛活性。

  DOI：

  10.1135/cccc19842649
• 作为产物：
  描述：

  邻甲苯基溴化镁 、 N-乙氧羰基-4-哌啶酮 以 乙醚 为溶剂， 反应 2.0h， 生成 1-乙氧羰基-4-(2-甲苯基)哌啶-4-醇
  参考文献：
  名称：

  Molecular-modeling based design, synthesis, and activity of substituted piperidines as γ-secretase inhibitors

  摘要：

  Alzheimer's disease (AD) is a debilitating disease widely thought to be associated with the accumulation of beta amyloid (A beta) in the brain. Inhibition of gamma-secretase, one of the enzymes responsible for A beta production, may be a useful strategy for the treatment of AD. Described below is a series of gamma-secretase inhibitors designed from a scaffold identified by a ROCS [J. Comput. Chem. 1996, 17, 1653] search of the corporate database. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.006

文献信息

• VEJDELEK, Z.;METYS, J.;HOLUBEK, J.;SVATEK, E.;PROTIVA, M., COLLECT. CZECHOSL. CHEM. COMMUN., 1984, 49, N 11, 2649-2660
  作者：VEJDELEK, Z.、METYS, J.、HOLUBEK, J.、SVATEK, E.、PROTIVA, M.

  DOI：——

  日期：——
• PROTIVA, MIROSLAV;SINDELAR, KAREL;METYS, JAN
  作者：PROTIVA, MIROSLAV、SINDELAR, KAREL、METYS, JAN

  DOI：——

  日期：——
• Potential antiparkinsonic agents: Synthesis and pharmacology of some 4-fluoro-4'-halogen'benzhydryl 2-(N,N-disubstituted amino)ethyl ethers
  作者：Zdeněk Vejdělek、Jan Metyš、Jiří Holubek、Emil Svátek、Miroslav Protiva

  DOI：10.1135/cccc19842649

  日期：——

  Reactions of 4,4'-dihalogenated benzhydrols and 1,1-diphenylethanols Xab and XIab with sodium hydride and 2-dimethylaminoethyl chloride and 2-pyrrolidinoethyl chloride afforded the ethers Vab-VIIIab. 2-Bromoethyl ethers IXab, obtained from the benzhydrols Xab and 2-bromoethanol by treatment with sulfuric acid, were subjected to substitution reactions with 4-phenylpiperidin-4-ol, 4-(2-tolyl)piperidin-4-ol (XVI), 4-(4-fluorophenyl)piperidin-4-ol and 4-(2-oxobenzimidazolin-1-yl)piperidine (XVII) and gave the amino ethers XIIab-XIVab and XIXab. The products were evaluated as potential antiparkinsonic agents and compared with flunamine (III). The ethers Va, Vb and VIa disclosed anticataleptic activity of a similar degree like that of flunamine (III).

  4,4'-二卤代苯基甲醇和1,1-二苯基乙醇Xab和XIab与氢氧化钠和2-二甲氨基乙基氯化物以及2-吡咯烷基乙基氯化物的反应产生了醚类化合物Vab-VIIIab。从苯基甲醇Xab和2-溴乙醇在硫酸的处理下得到2-溴乙基醚类化合物IXab，随后将其进行取代反应，反应物为4-苯基哌啶-4-醇、4-(2-甲苯基)哌啶-4-醇（XVI）、4-(4-氟苯基)哌啶-4-醇和4-(2-氧代苯并咪唑啉-1-基)哌啶（XVII），产生了氨基醚类化合物XIIab-XIVab和XIXab。这些产物被评估为潜在的抗帕金森病药物，并与flunamine（III）进行比较。醚类化合物Va、Vb和VIa显示了与flunamine（III）相似的抗痉挛活性。
• Molecular-modeling based design, synthesis, and activity of substituted piperidines as γ-secretase inhibitors
  作者：Eric Gundersen、Kristi Fan、Kimberly Haas、Donna Huryn、J. Steven Jacobsen、Anthony Kreft、Robert Martone、Scott Mayer、June Sonnenberg-Reines、Shaiu-Ching Sun、Hua Zhou

  DOI：10.1016/j.bmcl.2005.02.006

  日期：2005.4

  Alzheimer's disease (AD) is a debilitating disease widely thought to be associated with the accumulation of beta amyloid (A beta) in the brain. Inhibition of gamma-secretase, one of the enzymes responsible for A beta production, may be a useful strategy for the treatment of AD. Described below is a series of gamma-secretase inhibitors designed from a scaffold identified by a ROCS [J. Comput. Chem. 1996, 17, 1653] search of the corporate database. (c) 2005 Elsevier Ltd. All rights reserved.