2-(pyridin-2-yl)-5-(trifluoromethyl)benzonitrile | 1401251-46-4

• 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: 2-(pyridin-2-yl)-5-(trifluoromethyl)benzonitrile
• 英文别名: 2-(2-Pyridinyl)-5-(trifluoromethyl)benzonitrile；2-pyridin-2-yl-5-(trifluoromethyl)benzonitrile
• CAS: 1401251-46-4
• 化学式: C₁₃H₇F₃N₂
• 分子量: 248.207
• InChiKey: XGZREHMFMGDLJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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

• 作为产物：
  描述：

  偶氮二异丁腈 、 2-[4-(三氟甲基)苯基]吡啶 在 氧气 、 copper diacetate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以53%的产率得到2-(pyridin-2-yl)-5-(trifluoromethyl)benzonitrile
  参考文献：
  名称：

  Copper-Mediated Direct Aryl C–H Cyanation with Azobisisobutyronitrile via a Free-Radical Pathway

  摘要：

  An unprecedented protocol for the copper-mediated direct cyanation of aryl C-H by employing 2,2'-azobisisobutyronitrwile (AIBN) as a free radical "CN" source is presented. The protocol not only provides a more efficient pathway for the synthesis of aryl nitriles in terms of the yields and the loading amount of copper salts but also, more importantly, represents a novel strategy for aryl C-H cyanation via a CN free-radical mechanism as compared to the CN anion-participating protocols often reported.

  DOI：

  10.1021/ol401404y

文献信息

• Copper-mediated C–H cyanation of (hetero)arenes with ethyl (ethoxymethylene)cyanoacetate as a cyanating agent
  作者：Chaorong Qi、Xiaohan Hu、Huanfeng Jiang

  DOI：10.1039/c7cc03384b

  日期：——

  A copper-mediated direct C–H cyanation reaction of (hetero)arenes with ethyl (ethoxymethylene)cyanoacetate as a safe cyanating agent has been developed.

  一种以铜为媒介的直接C-H氰化反应已经开发出来，使用乙基（乙氧亚甲基）氰乙酸乙酯作为安全的氰化试剂，可用于(hetero)芳烃的氰化。
• Copper-catalyzed cyanation of arenes using benzyl nitrile as a cyanide anion surrogate
  作者：Jisong Jin、Qiaodong Wen、Ping Lu、Yanguang Wang

  DOI：10.1039/c2cc35046g

  日期：——

  The copper-catalyzed cyanation of arenes using benzyl nitrile as a cyanide anion surrogate furnishes aromatic nitriles in moderate to good yields. The cascade process involves a copper-catalyzed aerobic C-H oxidation, a retro-cyanohydrination, and a copper-catalyzed aerobic oxidative C-H functionalization.

  使用苄基腈作为氰化物阴离子替代物进行的铜催化的芳烃氰化，可提供中等至良好收率的芳族腈。级联过程涉及铜催化的好氧CH氧化，逆向氰化和铜催化的好氧氧化CH官能化。
• Copper-Catalyzed Aromatic CH Bond Cyanation by CCN Bond Cleavage of Inert Acetonitrile
  作者：Xuezhen Kou、Mengdi Zhao、Xixue Qiao、Yamin Zhu、Xiaofeng Tong、Zengming Shen

  DOI：10.1002/chem.201303637

  日期：2013.12.9

  Cut and paste! A Cu‐catalyzed aromatic CH cyanation with acetonitrile as the nitrile source by CCN cleavage has been developed (see scheme; TMEDA=N,N,N′,N′‐tetramethylethylenediamine). The reaction is catalytic in copper, and it is found that using (Me3Si)2 as an additive plays a critical role in promoting CCN cleavage and enhancing the reaction rate.

  剪切和粘贴！已开发出一种通过CCN裂解的乙腈为腈源的Cu催化的芳族CH氰化反应（参见方案； TMEDA = N，N，N ′，N′-四甲基乙二胺）。该反应在铜中是催化的，发现使用（Me 3 Si）2作为添加剂在促进CCN裂解和提高反应速率方面起着关键作用。
• A Pd(<scp>ii</scp>)/Mg–La mixed oxide catalyst for cyanation of aryl C–H bonds and tandem Suzuki–cyanation reactions
  作者：Ramineni Kishore、Jagjit Yadav、Boosa Venu、Akula Venugopal、M. Lakshmi Kantam

  DOI：10.1039/c5nj00585j

  日期：——

  A palladium(II)/magnesium–lanthanum mixed oxide (Pd(II)/Mg–La) catalyst is a reusable catalyst for cyanation of aromatic C–H bonds by using the combination of NH4HCO3 and DMSO as the ‘‘CN’’ source. Moderate to good yields of aromatic nitriles were obtained. An excellent regioselectivity was achieved using the present protocol. A tandem process involving Suzuki coupling followed by a cyanation reaction

  钯（II）/镁-镧混合氧化物（Pd（II）/ Mg-La）催化剂是可重复使用的催化剂，通过使用NH 4 HCO 3和DMSO的组合将芳族CH键氰化'' 资源。获得了中等至良好产率的芳族腈。使用本方案实现了极好的区域选择性。还使用非均相（Pd（II）/ Mg-La）催化剂开发了涉及Suzuki偶联并随后发生氰化反应的串联过程。该级联过程导致由简单的2-卤代吡啶形成芳族腈。通过离心回收催化剂，并以连续的三个循环重复使用，具有几乎一致的活性和选择性。
• Cobalt-Catalyzed C–H Cyanation of (Hetero)arenes and 6-Arylpurines with <i>N</i>-Cyanosuccinimide as a New Cyanating Agent
  作者：Amit B. Pawar、Sukbok Chang

  DOI：10.1021/ol503680d

  日期：2015.2.6

  A cobalt-catalyzed C–H cyanation reaction of arenes has been developed using N-cyanosuccinimide as a new electrophilic cyanating agent. The reaction proceeds with high selectivity to afford monocyanated products with excellent functional group tolerance. Substrate scope was found to be broad enough to include a wide range of heterocycles including 6-arylpurines.

  使用N-氰基琥珀酰亚胺作为新型的亲电子氰化剂，已开发出钴催化芳烃的CH氰化反应。反应以高选择性进行，得到具有优异的官能团耐受性的单氰酸酯化产物。发现底物的范围足够宽，可以包括包括6-芳基嘌呤在内的各种杂环。