2-(pyridin-2-yl)cyclopent-1-enecarbonitrile | 1581695-42-2

• 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)cyclopent-1-enecarbonitrile
• 英文别名: 2-Pyridin-2-ylcyclopentene-1-carbonitrile
• CAS: 1581695-42-2
• 化学式: C₁₁H₁₀N₂
• 分子量: 170.214
• InChiKey: PZOZPIDASKDVIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-[2]吡啶基-环戊醇 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 硫酸 、 copper(II) acetate monohydrate 作用下， 以 2-甲基-2-丁醇 、 水 为溶剂， 反应 12.25h， 生成 2-(pyridin-2-yl)cyclopent-1-enecarbonitrile
  参考文献：
  名称：

  Rhodium-Catalyzed Cyanation of C(sp²)–H Bond of Alkenes

  摘要：

  Efficient and selective rhodium-catalyzed cyanation of chelation-assisted C-H bonds of alkenes has been accomplished using environmentally benign N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as a cyanating reagent. The developed methodology tolerates various functional groups and allows the synthesis of diverse substituted acrylonitriles in good to excellent yields. Furthermore, the potential of the methodology was demonstrated through the formal synthesis of chlorpheniramine-based antagonist.

  DOI：

  10.1021/acs.orglett.5b01746

文献信息

• Copper-Catalyzed C–H Stereoselective Cyanation of Alkenes by Using an α-Iminonitrile as a Cyanating Reagent
  作者：Yong-Ming Zhu、Zhen-Bang Chen、Qing-Qing Gao、Kui Liu

  DOI：10.1055/s-0037-1610680

  日期：2019.1

  Abstract The first copper-catalyzed cyanation through alkene C–H bond activation by using an α-iminonitrile as a cyanating agent has been realized. The approach efficiently constructs acrylonitriles in good yields with the advantages of high regioselectivity, cost-benefit, and operational simplicity. The first copper-catalyzed cyanation through alkene C–H bond activation by using an α-iminonitrile

  摘要 通过使用α-亚甲基腈作为氰化剂，通过烯烃CH键的活化，首次实现了铜催化的氰化反应。该方法以高区域选择性，成本效益和操作简便性的优点，以高收率高效地构建了丙烯腈。 通过使用α-亚甲基腈作为氰化剂，通过烯烃CH键的活化，首次实现了铜催化的氰化反应。该方法以高区域选择性，成本效益和操作简便性的优点，以高收率高效地构建了丙烯腈。
• Rhodium(<scp>iii</scp>)-catalyzed cyanation of vinylic C–H bonds: N-cyano-N-phenyl-p-toluenesulfonamide as a cyanation reagent
  作者：Wei Su、Tian-Jun Gong、Bin Xiao、Yao Fu

  DOI：10.1039/c4cc09790d

  日期：——

  Rh(iii)-catalyzed direct vinylic C–H cyanation reaction has been developed as a practical method for the synthesis of alkenyl nitriles.

  Rh(III)-催化的直接烯基C-H氰化反应已被开发为合成烯基腈的实用方法。
• Rhodium-Catalyzed Direct C–H Bond Cyanation of Arenes with Isocyanide
  作者：Xiaohu Hong、Hao Wang、Guangyin Qian、Qitao Tan、Bin Xu

  DOI：10.1021/jo500087g

  日期：2014.4.4

  An efficient rhodium-catalyzed regioselective C-H bond cyanation of arenes was developed using tert-butyl isocyanide as the cyanide source. A wide range of (hetero)aryl and cycloalkenyl nitriles could be afforded with high regioselectivity and good functional group tolerance.