2-methyl-1-phenethylpiperidine | 139158-05-7

• 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: 2-methyl-1-phenethylpiperidine
• 英文别名: 2-Methyl-1-(2-phenylethyl)piperidine
• CAS: 139158-05-7
• 化学式: C₁₄H₂₁N
• 分子量: 203.327
• InChiKey: SDUYDMAVEHKRHA-UHFFFAOYSA-N

物化性质

• 沸点：
  148-149 °C(Press: 27 Torr)
• 密度：
  0.9401 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-1-phenethylpiperidine 在 mercury(II) diacetate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.58h， 生成
  参考文献：
  名称：

  Structure-activity studies of morphine fragments. II. Synthesis, opiate receptor binding, analgetic activity and conformational studies of 2-R-2(hydroxybenzyl)piperidines

  摘要：

  In this study, a series of 2-benzyl piperidines, that can be regarded as flexible fragments of fused ring opioids, have been synthesized and their pharmacological and conformational profiles determined. These combined studies reveal that, despite the weak activity of the only analog previously reported, modifications of it can lead to compounds with significant opioid receptor affinity and analgetic activity. Conformational studies of these compounds indicate that they can bind to these receptors in either an phenyl-axial and phenyl-equatorial conformer. Features such as the position of the phenolic OH group, the nature of the other 2-substituent and of the N-substituent appear to modulate receptor recognition and activation. However, the 2-benzyl piperidines do not appear to bind or act at the opioid receptors in the same conformation or orientation as their more rigid fused ring counterparts, the benzomorphans. In general, a change from p-OH to m-OH benzyl analogs reduces efficacy and its is possible that the m-OH analogs could be promising analgesics with low physical dependence liability.

  DOI：

  10.1016/0223-5234(91)90002-5
• 作为产物：
  描述：

  在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-methyl-1-phenethylpiperidine
  参考文献：
  名称：

  Hydroamination of terminal alkynes with secondary amines catalyzed by copper: regioselective access to amines

  摘要：

  一种简单方便的铜催化芳基乙炔与二级胺的氢胺化反应已经进行，经过氢胺化产物（E-烯胺）还原后，简单地获得脂肪胺的途径。

  DOI：

  10.1039/c5cc02677f

文献信息

• Efficient and Chemoselective Reduction of Pyridines to Tetrahydropyridines and Piperidines<i>via</i>Rhodium-Catalyzed Transfer Hydrogenation
  作者：Jianjun Wu、Weijun Tang、Alan Pettman、Jianliang Xiao

  DOI：10.1002/adsc.201201034

  日期：2013.1.14

  [Cp*RhCl2]2, catalyzes efficiently the transfer hydrogenation of various quaternary pyridinium salts under mild conditions, affording not only piperidines but also 1,2,3,6‐tetrahydropyridines in a highly chemoselective fashion, depending on the substitution pattern at the pyridinium ring. The reduction is conducted in azeotropic formic acid/triethylamine (HCOOH‐Et3N) mixture at 40 °C, with catalyst loadings

  在碘化物阴离子的作用下，铑络合物二聚体[Cp * RhCl 2 ] 2在温和的条件下有效催化各种季铵盐的转移氢化，不仅提供哌啶，而且还提供高度化学选择性的1,2,3,6-四氢吡啶取决于吡啶环上的取代方式。还原反应是在40°C的共沸甲酸/三乙胺（HCOOH-Et 3 N）混合物中进行的，催化剂负载量低至0.005 mol％是可行的。
• <i>cine</i>-Silylative Ring-Opening of α-Methyl Azacycles Enabled by the Silylium-Induced C–N Bond Cleavage
  作者：Jianbo Zhang、Sukbok Chang

  DOI：10.1021/jacs.0c05241

  日期：2020.7.22

  exo-dehydrogenation of alicyclic amine, (ii) hydrosilylation of resultant enamine, (iii) silylium-induced cis-β-amino elimination to open the ring skeleton, and (iv) hydrosilylation of terminal olefin. The present borane catalysis also works efficiently for the C-N bond cleavage of acyclic tertiary amines. On the basis of experimental and computational studies, the silicon atom was elucidated to play a pivotal

  本文描述了硼烷催化的α-甲基氮杂环的电影-甲硅烷基化开环的开发。这种转化涉及四步级联过程：(i) 脂环胺的外脱氢，(ii) 所得烯胺的氢化硅烷化，(iii) 甲硅烷诱导的顺式-β-氨基消除以打开环骨架，以及 (iv) 氢化硅烷化端烯烃。本硼烷催化对于无环叔胺的 CN 键断裂也有效。在实验和计算研究的基础上，阐明了硅原子在 β-氨基消除步骤中起关键作用。
• Radical cyclisations of imines and hydrazones
  作者：W. Russell Bowman、Peter T. Stephenson、Nicholas K. Terrett、Adrian R. Young

  DOI：10.1016/0040-4020(95)00412-2

  日期：1995.7

  Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH

  sp 3碳中心自由基在亚胺和上的自由基环化为合成5和6元环氮杂环提供了一种新方法。到C = N基团的亲电子碳上的环化和5 exo立体电子选择性是主要的机械参数。使用Bu 3 SnH由苯硒基前体生成C中心自由基中间体。
• Pyrrolidines, Piperidines and Hexahydroazepines from Glycols
  作者：Ralph M. Hill、Homer Adkins

  DOI：10.1021/ja01272a015

  日期：1938.5
• Hydroamination of terminal alkynes with secondary amines catalyzed by copper: regioselective access to amines
  作者：Janet Bahri、Rémi Blieck、Bassem Jamoussi、Marc Taillefer、Florian Monnier

  DOI：10.1039/c5cc02677f

  日期：——

  A simple and convenient copper-catalyzed hydroamination of arylacetylenes with secondary amines has been performed giving a simple access to aliphatic amines after reduction of the hydroaminated products (E-enamines).

  一种简单方便的铜催化芳基乙炔与二级胺的氢胺化反应已经进行，经过氢胺化产物（E-烯胺）还原后，简单地获得脂肪胺的途径。