2-(piperidin-1-yl)-3-trifluoromethylpyridine | 220459-51-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(piperidin-1-yl)-3-trifluoromethylpyridine
• 英文别名: 1-(3-trifluoromethylpyridin-2-yl)piperidine；2-Piperidino-3-(trifluoromethyl)pyridine；2-piperidin-1-yl-3-(trifluoromethyl)pyridine
• CAS: 220459-51-8
• 化学式: C₁₁H₁₃F₃N₂
• mdl: MFCD22192541
• 分子量: 230.233
• InChiKey: ZNYHIWMJPXRGPV-UHFFFAOYSA-N

物化性质

• 沸点：
  291.4±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(piperidin-1-yl)-3-trifluoromethylpyridine 在 盐酸 、 copper(ll) sulfate pentahydrate 、 十二羰基三钌 、 platinum(IV) oxide hydrate 、 氢气 、 silica gel 、 一水合肼 、 1,3-丙二醇 作用下， 以 异戊醇 、 二氯甲烷 、 邻二甲苯 、 异丙醇 为溶剂， 反应 42.5h， 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：

  哌啶 、 2-氯-3-三氟甲基吡啶 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以79%的产率得到2-(piperidin-1-yl)-3-trifluoromethylpyridine
  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

• [EN] NON-LYSOSOMAL GLUCOSYLCERAMIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE GLUCOSYLCÉRAMIDASE NON LYSOSOMALE ET LEURS UTILISATIONS
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2020229968A1

  公开（公告）日：2020-11-19

  The invention provides compounds for inhibiting glucosylceramidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds.

  这项发明提供了用于抑制葡萄糖酰胺酶的化合物，这些化合物的前药，以及包括这些化合物或这些化合物的前药的药物组合物。
• [EN] NON-LYSOSOMAL GLUCOSYLCERAMIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE LA GLUCOSYLCÉRAMIDASE NON LYSOSOMALE ET LEURS UTILISATIONS
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2021224865A1

  公开（公告）日：2021-11-11

  The invention provides compounds for inhibiting glucosylceramidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds.

  这项发明提供了用于抑制葡萄糖酰胺酶的化合物，这些化合物的前药以及包括这些化合物或化合物的前药的药物组合物。
• [EN] NON-LYSOSOMAL GLUCOSYLCERAMIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE GLUCOSYLCÉRAMIDASES NON LYSOSOMALES ET LEURS UTILISATIONS
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2021224864A1

  公开（公告）日：2021-11-11

  The invention provides compounds for inhibiting glucosylceramidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds.

  该发明提供了用于抑制葡萄糖酰胺酶的化合物，这些化合物的前药，以及包括这些化合物或化合物的前药的药物组合物。
• 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.