4-methoxy-2-(pyridin-2-yl)benzonitrile | 1443422-62-5

• 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-methoxy-2-(pyridin-2-yl)benzonitrile
• 英文别名: 4-Methoxy-2-pyridin-2-ylbenzonitrile；4-methoxy-2-pyridin-2-ylbenzonitrile
• CAS: 1443422-62-5
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: QHLQYUXEDSAARA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(3-methoxyphenyl)pyridine 、 2-氰基-3-乙氧基丙烯酸乙酯 在 氧气 、 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 130.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以86%的产率得到4-methoxy-2-(pyridin-2-yl)benzonitrile
  参考文献：
  名称：

  Copper-mediated C–H cyanation of (hetero)arenes with ethyl (ethoxymethylene)cyanoacetate as a cyanating agent

  摘要：

  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。

  DOI：

  10.1039/c7cc03384b

文献信息

• 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。
• 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。
• Rhodium(<scp>iii</scp>)-catalyzed aromatic C–H cyanation with dimethylmalononitrile as a cyanating agent
  作者：He Li、Sheng Zhang、Xiaoqiang Yu、Xiujuan Feng、Yoshinori Yamamoto、Ming Bao

  DOI：10.1039/c8cc08930b

  日期：——

  A rhodium-catalyzed aromatic C–H bond direct cyanation with safe, bench-stable, and commercially available dimethylmalononitrile as the cyanating agent has been successfully developed by using copper oxide as a promotor. Pyridine, quinoline, pyrimidine and pyrazole were used as the directing group in this type of C–H bond direct cyanation reaction.

  通过使用氧化铜作为促进剂，成功开发出了铑催化的芳香族CH键直接氰化，安全，稳定和可商购的二甲基丙二腈作为氰化剂。吡啶，喹啉，嘧啶和吡唑被用作这种C–H键直接氰化反应的导向基团。
• Copper-Mediated Direct Aryl C–H Cyanation with Azobisisobutyronitrile via a Free-Radical Pathway
  作者：Hao Xu、Peng-Tang Liu、Yun-Hui Li、Fu-She Han

  DOI：10.1021/ol401404y

  日期：2013.7.5

  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.
• Rhodium Catalyzed Cyanation of Chelation Assisted C–H Bonds
  作者：Manthena Chaitanya、Dongari Yadagiri、Pazhamalai Anbarasan

  DOI：10.1021/ol402201c

  日期：2013.10.4

  A rhodium-catalyzed cyanation of chelation assisted C-H bonds is described employing N-cyano-N-phenyl-p-methylbenzenesulfonamide as an efficient cyanating reagent. The present method allowed the synthesis of various benzonitirle derivatives in good to excellent yield. A number of chelating groups are also effective in the present cyanation of C-H bonds. In addition, the developed methodology was applied in the formal synthesis of the isoquinoline alkaloid, menisporphine.