4-[(3,4-二甲基苯基)甲基]-哌啶 | 782504-68-1

• 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: 4-[(3,4-二甲基苯基)甲基]-哌啶
• 中文别名: 嘧啶正离子,1-甲基-5-苯基-
• 英文名称: 4-[(3,4-dimethylphenyl)methyl]piperidine
• 英文别名: 4-(3,4-Dimethyl-benzyl)-piperidine
• CAS: 782504-68-1
• 化学式: C₁₄H₂₁N
• mdl: MFCD05863588
• 分子量: 203.327
• InChiKey: UGDSMWFVBHRRCG-UHFFFAOYSA-N

物化性质

• 沸点：
  94-96 °C(Press: 0.023 Torr)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(5-hydroxy-1H-indol-3-yl)ethanone 、 4-[(3,4-二甲基苯基)甲基]-哌啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以35%的产率得到2-(4-(3,4-dimethylbenzyl)piperidin-1-yl)-1-(5-hydroxy-1H-indol-3-yl)ethanone
  参考文献：
  名称：

  Structure-guided design of new indoles as negative allosteric modulators (NAMs) of N-methyl-d-aspartate receptor (NMDAR) containing GluN2B subunit

  摘要：

  Negative allosteric modulators (NAMs) of GluN2B-containing NMDARs provide pharmacological tools for the treatment of chronic neurodegenerative diseases. Novel NAMs have been designed on the basis of computational studies focused on the 'hit compound' 3. This series of indoles has been tested in competition assay. Compounds 16 and 17 were the most active ligands (IC50 values of 83 nM and 71 nM, respectively) and they showed a potency close to that of reference compounds ifenprodil (1, IC50 = 47 nM) and 3 (IC50 = 25 nM). Furthermore, docking studies have been performed for active ligand 16 and the results were in a good agreement with biological data. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.02.021
• 作为产物：
  描述：

  magnesium,1,2-dimethylbenzene-5-ide,bromide 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0~60.0 ℃ 、100.0 kPa 条件下， 反应 10.0h， 生成 4-[(3,4-二甲基苯基)甲基]-哌啶
  参考文献：
  名称：

  2-和4-取代苄基哌啶的方便、良性和可扩展的合成

  摘要：

  2-和4-取代苄基哌啶的短时间、可扩展和环境友好的合成已经被开发。该方法基于在 Pd 存在下芳基（吡啶-2-基）-和芳基（吡啶-4-基）甲醇和芳基（吡啶-4-基）甲酮的程序升温连续脱氧和杂芳环饱和/C 催化剂。温度、酸度和底物结构在选择性变化中的关键作用已通过几种取代芳基（哌啶）甲醇的分离得到证实。甲醇和酮由市售的吡啶甲醛或 4-氰基吡啶和取代的溴苯通过有机金属中间体制备。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400215

文献信息

• Structure-guided design of new indoles as negative allosteric modulators (NAMs) of N-methyl-d-aspartate receptor (NMDAR) containing GluN2B subunit
  作者：Maria Rosa Buemi、Laura De Luca、Stefania Ferro、Emilio Russo、Giovambattista De Sarro、Rosaria Gitto

  DOI：10.1016/j.bmc.2016.02.021

  日期：2016.4

  Negative allosteric modulators (NAMs) of GluN2B-containing NMDARs provide pharmacological tools for the treatment of chronic neurodegenerative diseases. Novel NAMs have been designed on the basis of computational studies focused on the 'hit compound' 3. This series of indoles has been tested in competition assay. Compounds 16 and 17 were the most active ligands (IC50 values of 83 nM and 71 nM, respectively) and they showed a potency close to that of reference compounds ifenprodil (1, IC50 = 47 nM) and 3 (IC50 = 25 nM). Furthermore, docking studies have been performed for active ligand 16 and the results were in a good agreement with biological data. (C) 2016 Elsevier Ltd. All rights reserved.
• Convenient, Benign and Scalable Synthesis of 2- and 4-Substituted Benzylpiperidines
  作者：Béla Ágai、Ágnes Proszenyák、Gábor Tárkányi、László Vida、Ferenc Faigl

  DOI：10.1002/ejoc.200400215

  日期：2004.9

  A short, scalable and environmentally benign synthesis of 2- and 4-substituted benzylpiperidines has been developed. The method is based on the temperature-programmed consecutive deoxygenation and heteroaromatic ring saturation of aryl(pyridin-2-yl)- and aryl(pyridin-4-yl)methanols and aryl(pyridin-4-yl)methanones in the presence of Pd/C catalyst. The crucial roles of the temperature, the acidity and

  2-和4-取代苄基哌啶的短时间、可扩展和环境友好的合成已经被开发。该方法基于在 Pd 存在下芳基（吡啶-2-基）-和芳基（吡啶-4-基）甲醇和芳基（吡啶-4-基）甲酮的程序升温连续脱氧和杂芳环饱和/C 催化剂。温度、酸度和底物结构在选择性变化中的关键作用已通过几种取代芳基（哌啶）甲醇的分离得到证实。甲醇和酮由市售的吡啶甲醛或 4-氰基吡啶和取代的溴苯通过有机金属中间体制备。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)