2-(2-chlorophenoxy)nicotinonitrile | 52203-98-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-chlorophenoxy)nicotinonitrile
• 英文别名: 2-(2-Chlorophenoxy)pyridine-3-carbonitrile
• CAS: 52203-98-2
• 化学式: C₁₂H₇ClN₂O
• mdl: MFCD09936870
• 分子量: 230.653
• InChiKey: QTHMKSBDFDPLHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-chlorophenoxy)nicotinonitrile 在 indium(III) chloride 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 六甲基二硅烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以53%的产率得到benzofurano<2,3-b>pyridine
  参考文献：
  名称：

  Rhodium-Catalyzed Silylation and Intramolecular Arylation of Nitriles via the Silicon-Assisted Cleavage of Carbon−Cyano Bonds

  摘要：

  A rhodium-catalyzed silylation reaction of carbon-cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from eta(2)-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.

  DOI：

  10.1021/ja804992n
• 作为产物：
  描述：

  2-氯-3-氰基吡啶 、 邻氯苯酚 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 10.17h， 以45%的产率得到2-(2-chlorophenoxy)nicotinonitrile
  参考文献：
  名称：

  Rhodium-Catalyzed Silylation and Intramolecular Arylation of Nitriles via the Silicon-Assisted Cleavage of Carbon−Cyano Bonds

  摘要：

  A rhodium-catalyzed silylation reaction of carbon-cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from eta(2)-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.

  DOI：

  10.1021/ja804992n

文献信息

• Rhodium-Catalyzed Silylation and Intramolecular Arylation of Nitriles via the Silicon-Assisted Cleavage of Carbon−Cyano Bonds
  作者：Mamoru Tobisu、Yusuke Kita、Yusuke Ano、Naoto Chatani

  DOI：10.1021/ja804992n

  日期：2008.11.26

  A rhodium-catalyzed silylation reaction of carbon-cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from eta(2)-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.