2-phenyl-1-[3-(trifluoromethyl)pyridin-2-yl]piperidine | 1431615-99-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-phenyl-1-[3-(trifluoromethyl)pyridin-2-yl]piperidine
• 英文别名: 2-Phenyl-1-(3-trifluoromethylpyridin-2-yl)piperidine；2-(2-phenylpiperidin-1-yl)-3-(trifluoromethyl)pyridine
• CAS: 1431615-99-4
• 化学式: C₁₇H₁₇F₃N₂
• 分子量: 306.331
• InChiKey: FEAMGGPKSMZMBT-UHFFFAOYSA-N

物化性质

• 沸点：
  402.5±45.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-phenyl-1-[3-(trifluoromethyl)pyridin-2-yl]piperidine 在 盐酸 、 platinum(IV) oxide hydrate 、 氢气 、 silica gel 、 一水合肼 作用下， 以 异戊醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 18.5h， 生成 2-苯基哌啶
  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
• 作为产物：
  描述：

  2-氯-3-三氟甲基吡啶 在 copper(ll) sulfate pentahydrate 、 十二羰基三钌 、 potassium carbonate 、 1,3-丙二醇 作用下， 以 邻二甲苯 、 乙腈 为溶剂， 反应 48.0h， 生成 2-phenyl-1-[3-(trifluoromethyl)pyridin-2-yl]piperidine
  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

• First selective direct mono-arylation of piperidines using ruthenium-catalyzed C–H activation
  作者：Maria C. Schwarz、Navid Dastbaravardeh、Karl Kirchner、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1007/s00706-013-0947-1

  日期：2013.4

  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.