2-(morpholin-4-yl)-3-trifluoromethylpyridine | 220459-52-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(morpholin-4-yl)-3-trifluoromethylpyridine
• 英文别名: 4-[3-(trifluoromethyl)pyridin-2-yl]morpholine；2-Morpholino-3-(trifluoromethyl)pyridine
• CAS: 220459-52-9
• 化学式: C₁₀H₁₁F₃N₂O
• mdl: MFCD25121766
• 分子量: 232.205
• InChiKey: YAUBVDRHLOCQJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  吗啉 、 2-氯-3-三氟甲基吡啶 以83%的产率得到2-(morpholin-4-yl)-3-trifluoromethylpyridine
  参考文献：
  名称：

  Nucleophilic displacement in 2-chloro(trifluoromethyl)pyridines with amines and ammonia

  摘要：

  The activating effect of trifluoromethyl groups in 2-chloro(trifluoromethyl)pyridines was investigated by comparing reactions of these compounds and of 2-chloropyridine with secondary cyclic amines. The ammonolysis of 2-chloro-3-trifluoromethylpyridine and 2-chloro-4-trifluoromethylpyridine is also reported and shown to proceed, in contrast to the reported behaviour of 2-chloro-5-trifluoromethylpyridine, without hydrolysis of the trifluoromethyl function. Both 2-amino-3-trifluoromethylpyridine and 2-amino-4-trifluoromethylpyridine were converted (via the corresponding pyridones) to 3-trifluoromethylpyridin-2(1H)-thione and 4-trifluoromethylpyridin-2(1H)-thione, and a number of S-alkyl derivatives of the latter compounds were prepared. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(98)00308-x

文献信息

• Nucleophilic displacement in 2-chloro(trifluoromethyl)pyridines with amines and ammonia
  作者：A.D Dunn

  DOI：10.1016/s0022-1139(98)00308-x

  日期：1999.2

  The activating effect of trifluoromethyl groups in 2-chloro(trifluoromethyl)pyridines was investigated by comparing reactions of these compounds and of 2-chloropyridine with secondary cyclic amines. The ammonolysis of 2-chloro-3-trifluoromethylpyridine and 2-chloro-4-trifluoromethylpyridine is also reported and shown to proceed, in contrast to the reported behaviour of 2-chloro-5-trifluoromethylpyridine, without hydrolysis of the trifluoromethyl function. Both 2-amino-3-trifluoromethylpyridine and 2-amino-4-trifluoromethylpyridine were converted (via the corresponding pyridones) to 3-trifluoromethylpyridin-2(1H)-thione and 4-trifluoromethylpyridin-2(1H)-thione, and a number of S-alkyl derivatives of the latter compounds were prepared. (C) 1999 Elsevier Science S.A. All rights reserved.
• 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.