6-[3-(三氟甲基)苯基]吡啶-2-甲腈 | 833457-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-[3-(三氟甲基)苯基]吡啶-2-甲腈
• 英文名称: 6-[3-(trifluoromethyl)phenyl]pyridine-2-carbonitrile
• 英文别名: 6-(3-(Trifluoromethyl)phenyl)picolinonitrile
• CAS: 833457-45-7
• 化学式: C₁₃H₇F₃N₂
• 分子量: 248.207
• InChiKey: FYQRYAIHFASLNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-[3-(三氟甲基)苯基]吡啶-2-甲腈 在 sodium methylate 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以96%的产率得到6-[3-(Trifluoromethyl)phenyl]pyridine-2-carboxamide
  参考文献：
  名称：

  2-PHENYL-6-AZOLYLPYRIDINE-BASED LIGAND AND GROUP VIII TRANSITION METAL COMPLEX

  摘要：

  一种基于2-苯基-6-氮杂吡啶的配体由以下公式（I）表示：其中，X代表氮或C—R10；R1、R2、R3、R4、R5、R6、R7、R8和R10独立地代表氢、卤素、氰基、氨基、可选择取代的芳基、可选择取代的杂环芳基、硫酸根、—COOH、烷氧基、羰基、C1-C10卤代烷基、C1-C12烷基、C2-C10烯基、C2-C10炔基、C3-C20环烷基、C3-C20环烯基、C1-C20杂环烷基或C1-C20杂环烯基；R9代表氢或碱金属。

  公开号：

  US20130018189A1
• 作为产物：
  描述：

  间溴三氟甲苯 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 16.5h， 生成 6-[3-(三氟甲基)苯基]吡啶-2-甲腈
  参考文献：
  名称：

  2-PHENYL-6-AZOLYLPYRIDINE-BASED LIGAND AND GROUP VIII TRANSITION METAL COMPLEX

  摘要：

  一种基于2-苯基-6-氮杂吡啶的配体由以下公式（I）表示：其中，X代表氮或C—R10；R1、R2、R3、R4、R5、R6、R7、R8和R10独立地代表氢、卤素、氰基、氨基、可选择取代的芳基、可选择取代的杂环芳基、硫酸根、—COOH、烷氧基、羰基、C1-C10卤代烷基、C1-C12烷基、C2-C10烯基、C2-C10炔基、C3-C20环烷基、C3-C20环烯基、C1-C20杂环烷基或C1-C20杂环烯基；R9代表氢或碱金属。

  公开号：

  US20130018189A1

文献信息

• [EN] ORGANOZINC COMPLEXES AND PROCESSES FOR MAKING AND USING THE SAME<br/>[FR] COMPLEXES D'ORGANOZINC ET PROCÉDÉS POUR LEUR FABRICATION ET LEUR UTILISATION
  申请人：UNIV MUENCHEN L MAXIMILIANS

  公开号：WO2012085168A1

  公开（公告）日：2012-06-28

  Processes for making an organozinc reagents are disclosed comprising reacting (A) organomagnesium or organozinc complexes with (B) at least one coordination compound comprising one or more carboxylate groups and/or alcoholate groups and/or tertiary amine groups, optionally in combination with zinc ions and/or lithium ions and/or halide ions, wherein the halide ions are selected from chloride, bromide and iodide, the organozinc complex comprises an aryl group, a heteroaryl group or a benzyl group when the coordinating compound is a chelating polyamine, and the reaction is conducted in the presence of zinc complexed with at least one coordinating compound when reactant (A) comprises at least one organomagnesium complex. The resulting organozinc reagents may optionally be isolated from solvents to obtain a solid reagent. The reagents may be used for making organic compounds via Negishi cross-coupling reactions or via aldehyde and/or ketone oxidative addition reactions. The organozinc reagents are stable and, due to their high selectivity, permit maintenance of sensitive functional groups such as aldehydes during cross-coupling.

  公开了制备有机锌试剂的方法，包括将（A）有机镁或有机锌配合物与（B）至少一种含有一个或多个羧酸基团和/或醇基团和/或三级胺基团的配位化合物反应，可选地与锌离子和/或锂离子和/或卤离子结合，其中卤离子选自氯离子、溴离子和碘离子，当配位化合物为螯合多胺时，有机锌配合物包括芳基、杂环芳基或苄基，当反应物（A）包含至少一种有机镁配合物时，在存在至少一种配位化合物与锌络合物的情况下进行反应。所得的有机锌试剂可以选择性地从溶剂中分离出来以获得固体试剂。这些试剂可用于通过Negishi交叉偶联反应或通过醛和/或酮氧化加成反应制备有机化合物。有机锌试剂稳定，并且由于其高选择性，允许在交叉偶联过程中保持敏感的官能团，如醛基。
• Preparation of Solid Salt-Stabilized Functionalized Organozinc Compounds and their Application to Cross-Coupling and Carbonyl Addition Reactions
  作者：Sebastian Bernhardt、Georg Manolikakes、Thomas Kunz、Paul Knochel

  DOI：10.1002/anie.201104291

  日期：2011.9.19

  Powdered organozinc reagents: Various aryl and heteroaryl bromides as well as benzylic chlorides react with Mg and Zn(OPiv)2⋅2 LiCl (OPiv=pivalate) to provide solid organozinc reagents after solvent evaporation. These powders can be stored at room temperature under argon for months and can be manipulated in air for a short time. They undergo smooth Negishi cross‐coupling and carbonyl addition reactions

  粉末状有机锌试剂：各种芳基和杂芳基溴化物，以及苄基氯化物与Mg和Zn反应（OPiv）2 ⋅2的LiCl（OPiv =新戊酸盐）溶剂蒸发后，以提供固体有机锌试剂。这些粉末可以在室温下于氩气中保存数月，并可以在空气中短时间操作。它们会进行平稳的Negishi交叉偶联和羰基加成反应（请参见方案）。
• ORGANOZINC COMPLEXES AND PROCESSES FOR MAKING AND USING THE SAME
  申请人：Knochel Paul

  公开号：US20140031545A1

  公开（公告）日：2014-01-30

  Processes for making an organozinc reagents are disclosed comprising reacting (A) organomagnesium or organozinc complexes with (B) at least one coordination compound comprising one or more carboxylate groups and/or alcoholate groups and/or tertiary amine groups, optionally in combination with zinc ions and/or lithium ions and/or halide ions, wherein the halide ions are selected from chloride, bromide and iodide, the organozinc complex comprises an aryl group, a heteroaryl group or a benzyl group when the coordinating compound is a chelating polyamine, and the reaction is conducted in the presence of zinc complexed with at least one coordinating compound when reactant (A) comprises at least one organomagnesium complex. The resulting organozinc reagents may optionally be isolated from solvents to obtain a solid reagent. The reagents may be used for making organic compounds via Negishi cross-coupling reactions or via aldehyde and/or ketone oxidative addition reactions. The organozinc reagents are stable and, due to their high selectivity, permit maintenance of sensitive functional groups such as aldehydes during cross-coupling.

  公开了制备有机锌试剂的工艺，包括将（A）有机镁或有机锌配合物与（B）至少一种配位化合物反应，该配位化合物包括一个或多个羧酸盐基和/或醇盐基和/或三级胺基，可选地与锌离子和/或锂离子和/或卤素离子组合，其中卤素离子选自氯离子、溴离子和碘离子，当配位化合物为螯合多胺时，有机锌配合物包括苯基、杂环基或苄基，并且当反应物（A）包括至少一个有机镁配合物时，在存在至少一种配位化合物的锌配合物的情况下进行反应。所得有机锌试剂可以选择从溶剂中分离出来以获得固体试剂。该试剂可用于通过Negishi交叉偶联反应或通过醛和/或酮氧化加成反应制备有机化合物。由于其高选择性，有机锌试剂稳定，并允许保持敏感的功能基团，如醛基在交叉偶联反应过程中。
• 4-(3-Trifluoromethylphenyl)-pyrimidine-2-carbonitrile as cathepsin S inhibitors: N3, not N1 is critically important
  作者：Jiaqiang Cai、Xavier Fradera、Mario van Zeeland、Maureen Dempster、Kenneth S. Cameron、D. Jonathan Bennett、John Robinson、Lucy Popplestone、Mark Baugh、Paul Westwood、John Bruin、William Hamilton、Emma Kinghorn、Clive Long、Joost C.M. Uitdehaag

  DOI：10.1016/j.bmcl.2010.06.043

  日期：2010.8

  Using computer aided modelling studies, a new extended P2/S2 interaction was identified. This extended region can accommodate a variety of functional groups, such as aryls and basic amines. It was discovered that the N3 nitrogen of the pyrimidine-2-carbonitrile is critical for its cathepsin cysteine protease inhibition. N1 nitrogen also contributes to the inhibitory activity, but to a very limited degree. An 'in situ double activation' mechanism was proposed to explain these results. (C) 2010 Elsevier Ltd. All rights reserved.
• US9273070B2
  申请人：——

  公开号：US9273070B2

  公开（公告）日：2016-03-01