2-(2-Chloro-4-methoxyphenoxy)-5-methoxybenzonitrile | 1082076-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-Chloro-4-methoxyphenoxy)-5-methoxybenzonitrile
• 英文别名: 2-(2-chloro-4-methoxyphenoxy)-5-methoxybenzonitrile
• CAS: 1082076-91-2
• 化学式: C₁₅H₁₂ClNO₃
• 分子量: 289.718
• InChiKey: QCQNYBZCNWRHFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-Chloro-4-methoxyphenoxy)-5-methoxybenzonitrile 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 六甲基二硅烷 、 三异丙基亚磷酸酯 作用下， 以 乙基环己烷 为溶剂， 反应 15.0h， 以65%的产率得到2,8-dimethoxydibenzo[b,d]furan
  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.