4-(6-chloropyridin-2-yl)benzonitrile | 13382-57-5

• 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
• 英文名称: 4-(6-chloropyridin-2-yl)benzonitrile
• 英文别名: 4-(6-Chloropyridin-2-yl)benzonitrile
• CAS: 13382-57-5
• 化学式: C₁₂H₇ClN₂
• 分子量: 214.654
• InChiKey: ANUHTNNEFBWJDW-UHFFFAOYSA-N

物化性质

• 沸点：
  379.4±32.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  3-(2-甲氧羰基乙基)苯基硼酸 、 4-(6-chloropyridin-2-yl)benzonitrile 在 三乙胺 作用下， 反应 12.0h， 生成
  参考文献：
  名称：

  A Micellar Catalysis Strategy for Suzuki–Miyaura Cross-Couplings of 2-Pyridyl MIDA Boronates: No Copper, in Water, Very Mild Conditions

  摘要：

  Suzuki-Miyaura (SM) cross-couplings of 2-pyridyl MIDA boronates can be successfully carried out in the complete absence of copper by attenuation of the Lewis basicity associated with the pyridyl nitrogen using selected substituents (e.g., fluorine or chlorine) on the ring. This strategy imparts additional synthetic options compared with existing approaches based on the use of Lewis acids or N-oxides. Thus, access to highly valued 2-substituted pyridyl rings via an initial Suzuki-Miyaura coupling can be followed by dehalogenation, SNAr reactions, or a second SM coupling to arrive at 2,6-disubstituted pyridyl arrays, all run in a single pot, enabled by micellar catalysis in water. Accessing targets within drug-like space is demonstrated in a four-step, one-pot sequence. Computational data suggest that the major role being played by electron-withdrawing substituents in promoting these cross-couplings without the need for copper is to slow the rates of protodeboronation of intermediate 2-pyridylboronic acids.

  DOI：

  10.1021/acscatal.7b03241
• 作为产物：
  描述：

  4-溴苯腈 、 potassium 6-chloropyridine-2-trifluoroborate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以26%的产率得到4-(6-chloropyridin-2-yl)benzonitrile
  参考文献：
  名称：

  钯催化的2-吡啶基三氟硼酸钾与芳基（杂芳基）卤化物的铃木-宫浦交叉偶联反应

  摘要：

  吡啶-2-三氟硼酸钾与各种芳基（杂芳基）卤化物的钯催化的Suzuki-Miyaura交叉偶联反应可以产生相应的所需偶联产物，产率中等至良好。可以在以下条件下进行：乙醇为溶剂，Pd（OAc）2和SPhos为催化剂体系，Na 2 CO 3为碱。

  DOI：

  10.1016/j.tet.2011.12.036

文献信息

• Palladium-catalyzed Suzuki–Miyaura cross-coupling reaction of potassium 2-pyridyl trifluoroborate with aryl (heteroaryl) halides
  作者：Wei Ren、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1016/j.tet.2011.12.036

  日期：2012.2

  Palladium-catalyzed Suzuki–Miyaura cross-coupling reaction of potassium pyridine-2-trifluoroborates and various aryl (heteroaryl) halides can generate the corresponding desired coupling products with moderate to good yields. It can be carried out under the conditions with ethanol as solvent, Pd(OAc)2 and SPhos as catalyst system and Na2CO3 as a base.

  吡啶-2-三氟硼酸钾与各种芳基（杂芳基）卤化物的钯催化的Suzuki-Miyaura交叉偶联反应可以产生相应的所需偶联产物，产率中等至良好。可以在以下条件下进行：乙醇为溶剂，Pd（OAc）2和SPhos为催化剂体系，Na 2 CO 3为碱。
• A Micellar Catalysis Strategy for Suzuki–Miyaura Cross-Couplings of 2-Pyridyl MIDA Boronates: <i>No Copper</i>, in Water, Very Mild Conditions
  作者：Nicholas A. Isley、Ye Wang、Fabrice Gallou、Sachin Handa、Donald H. Aue、Bruce H. Lipshutz

  DOI：10.1021/acscatal.7b03241

  日期：2017.12.1

  Suzuki-Miyaura (SM) cross-couplings of 2-pyridyl MIDA boronates can be successfully carried out in the complete absence of copper by attenuation of the Lewis basicity associated with the pyridyl nitrogen using selected substituents (e.g., fluorine or chlorine) on the ring. This strategy imparts additional synthetic options compared with existing approaches based on the use of Lewis acids or N-oxides. Thus, access to highly valued 2-substituted pyridyl rings via an initial Suzuki-Miyaura coupling can be followed by dehalogenation, SNAr reactions, or a second SM coupling to arrive at 2,6-disubstituted pyridyl arrays, all run in a single pot, enabled by micellar catalysis in water. Accessing targets within drug-like space is demonstrated in a four-step, one-pot sequence. Computational data suggest that the major role being played by electron-withdrawing substituents in promoting these cross-couplings without the need for copper is to slow the rates of protodeboronation of intermediate 2-pyridylboronic acids.