2-苯基-1-(3,4,5,6-四氢吡啶-2-基)哌啶 | 1261144-90-4

• 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: 2-苯基-1-(3,4,5,6-四氢吡啶-2-基)哌啶
• 英文名称: 2-phenyl-1-(3,4,5,6-tetrahydropyridin-2-yl)piperidine
• 英文别名: 6-(2-phenylpiperidin-1-yl)-2,3,4,5-tetrahydropyridine
• CAS: 1261144-90-4
• 化学式: C₁₆H₂₂N₂
• 分子量: 242.364
• InChiKey: QZICHATUYSPWGT-UHFFFAOYSA-N

物化性质

• 沸点：
  404.3±34.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-苯基-1-(3,4,5,6-四氢吡啶-2-基)哌啶 在 一水合肼 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 2.5h， 以47%的产率得到2-苯基哌啶
  参考文献：
  名称：

  通过直接过渡金属催化的sp3 C对哌啶进行C-2酰化反应？H激活

  摘要：

  您只需要一个开放的小瓶！环状烷基胺的直接α芳基化反应（请参见方案）需要一个开放的小瓶，因为参与C（sp 3）H活化过程的氢原子最终会以氢气的形式释放出来。关于在直接过渡金属催化的官能化反应中形成氢气的报道仍然很少。小瓶反应证明对这种直接芳构化过程至关重要，因为密封后会发生催化剂失活。

  DOI：

  10.1002/chem.201001887
• 作为产物：
  描述：

  2-phenyl-1-[3-(trifluoromethyl)-3,4,5,6-tetrahydropyridin-2-yl]piperidine 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以252 mg的产率得到2-苯基-1-(3,4,5,6-四氢吡啶-2-基)哌啶
  参考文献：
  名称：

  First selective direct mono-arylation of piperidines using ruthenium-catalyzed C–H activation

  摘要：

  A Ru-catalyzed mono-arylation in alpha-position of saturated cyclic amines is reported employing a C-H activation protocol. Substitution of the pyridine directing group with a bulky group, e.g., trifluoromethyl in the 3-position, proved to be crucial to avoid bis-arylation. This highly selective transformation can be performed with different amines and arylboronate esters. Additionally, the directing group can be cleaved, taking advantage of an unprecedented detrifluoromethylation reaction.

  DOI：

  10.1007/s00706-013-0947-1

文献信息

• Removal of the Pyridine Directing Group from α-Substituted<i>N</i>-(Pyridin-2-yl)piperidines Obtained via Directed Ru-Catalyzed sp³C–H Functionalization
  作者：Veerle Smout、Aldo Peschiulli、Stefan Verbeeck、Emily A. Mitchell、Wouter Herrebout、Patrick Bultinck、Christophe M. L. Vande Velde、Didier Berthelot、Lieven Meerpoel、Bert U. W. Maes

  DOI：10.1021/jo401521y

  日期：2013.10.4

  Two strategies, "hydrogenation-hydride reduction" and. "quaternization-hydride reduction", are reported, that make use of mild reaction conditions (room temperature) to efficiently remove the N-pyridin-2-yl directing group from a diverse set of C-2-substituted piperidines that were synthesized through directed Ru-catalyzed Sp(3) C-H functionalization. The deprotected products are obtained in moderate to good overall yields irrespective of the strategy followed, indicating that both methods are generally. equally effective. Only in the case of 2,6-disubstituted piperidines, could the "quaternization-hydride reduction" strategy not be used. The "hydrogenation-hydride reduction" protocol was successfully applied to trans- and cis-2-methyl-N-(pyridin-2-yl)-6-undecylpiperidine in a short synthetic route toward (+/-)-solenopsin A (trans diastereoisomer) and (+/-)-isosolenopsin A (cis diastereoisomer). The absolute configuration of the enantiomers of these fire: ant alkaloids could be determined via VCD spectroscopy.