N-[2-(3,4-dimethoxyphenyl)ethyl]piperidine | 71642-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-(3,4-dimethoxyphenyl)ethyl]piperidine
• 英文别名: 1-(3,4-dimethoxy-phenethyl)-piperidine；1-(3,4-Dimethoxy-phenaethyl)-piperidin；1-[2-(3,4-Dimethoxyphenyl)ethyl]piperidine
• CAS: 71642-81-4
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: TUBIOWZLDWTANZ-UHFFFAOYSA-N

物化性质

• 沸点：
  126-127.5 °C(Press: 0.5 Torr)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯乙醇 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 12.0h， 生成 N-[2-(3,4-dimethoxyphenyl)ethyl]piperidine
  参考文献：
  名称：

  在prazosin中搜索用于Transport-P的药效团。

  摘要：

  已经合成了哌唑嗪的部分结构，并测试了其对Transport-P的抑制作用，以鉴定吡唑啉的结构特征，该结构特征似乎与推定的转运蛋白结合。已经表明，嘧啶基4-氨基对于结合至关重要，但是6，7-二甲氧基和2-呋喃基不是必需的。

  DOI：

  10.1016/j.bmc.2005.03.030

文献信息

• Ruthenium catalyzed synthesis of secondary or tertiary amines from amines and alcohols
  作者：Shun-Ichi Murahashi、Kaoru Kondo、Toshiyuki Hakata

  DOI：10.1016/s0040-4039(00)86792-1

  日期：1982.1

  Unsymmetrical secondary and tertiary amines are prepared by the ruthenium catalyzed reaction of alcohols with amines, which provides highly efficient method for synthesis of cyclic amines.

  不对称仲胺和叔胺是通过醇与胺的钌催化反应制备的，这为合成环状胺提供了高效的方法。
• Ambient Moisture Accelerates Hydroamination Reactions of Vinylarenes with Alkali‐Metal Amides under Air
  作者：Florian F. Mulks、Leonie J. Bole、Laia Davin、Alberto Hernán‐Gómez、Alan Kennedy、Joaquín García‐Álvarez、Eva Hevia

  DOI：10.1002/anie.202008512

  日期：2020.10.19

  A straightforward alkali‐metal‐mediated hydroamination of styrenes using biorenewable 2‐methyltetrahydrofuran as a solvent is reported. Refuting the conventional wisdom of the incompatibility of organolithium reagents with air and moisture, shown here is that the presence of moisture is key in favoring formation of the target phenethylamines over competing olefin polymerization products. The method

  据报道，使用可生物再生的2-甲基四氢呋喃作为溶剂进行的直接的碱金属介导的苯乙烯加氢胺化反应。驳斥有机锂试剂与空气和水分不相容的传统观点，此处表明，水分的存在是形成目标苯乙胺优于竞争性烯烃聚合产物的关键。该方法也与氨基钠兼容，后者在惰性气氛条件下作为高效催化剂显示出极好的前景。
• CONVERSION OF NITRILES INTO TERTIARY AMINES: N,N-DIMETHYLHOMOVERATRYLAMINE
  作者：Rousselet, Guilhem、Capdevielle, Patrice、Maumy, Michel、Derrer, Sam、Holmes, Andrew B.

  DOI：10.15227/orgsyn.076.0133

  日期：——
• Anti-Markovnikov Functionalization of Olefins: Rhodium-Catalyzed Oxidative Aminations of Styrenes
  作者：Matthias Beller、Martin Eichberger、Harald Trauthwein

  DOI：10.1002/anie.199722251

  日期：1997.11.3
• Rhodium-Catalyzed Anti-Markovnikov Hydroamination of Vinylarenes
  作者：Masaru Utsunomiya、Ryoichi Kuwano、Motoi Kawatsura、John F. Hartwig

  DOI：10.1021/ja0293608

  日期：2003.5.1

  The transition metal-catalyzed anti-Markovnikov hydroamination of unactivated vinylarenes with a rhodium complex of DPEphos is reported. The reaction of electron-neutral or electron-rich vinylarenes with a variety of secondary amines in the presence of catalyst forms the products from anti-Markovnikov hydroamination in high yields. Reactions of morpholine, N-phenylpiperazine, N-Boc-piperazine, piperidine, 2,5-dimethylmorpholine, and perhydroisoquinoline reacted with styrene to form the amine product in 51-71% yield. Reactions of a variety of vinylarenes with morpholine generated amine as the major product. Reactions of morpholine with electron-poor vinylarenes gave lower amine:enamine ratios than reactions of electron-rich vinylarenes at the same concentration of vinylarene, but conditions were developed with lower concentrations of electron-poor vinylarene to maintain formation of the amine as the major product. Reactions of dimethylamine with vinylarenes were fast and formed amine as the major product. Mechanistic studies on the hydroamination process showed that the amine:enamine ratio was lower for reactions conducted with higher concentrations of vinylarene and that one vinylarene influences the selectivity for reaction of another. A mechanism proceeding through a metallacyclic intermediate that opens in the presence of a second vinylarene accounts for these and other mechanistic observations.