2-(dicyclohexylphosphino)-2'-hydroxy-1,1'-binaphthyl | 908293-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(dicyclohexylphosphino)-2'-hydroxy-1,1'-binaphthyl
• 英文别名: Cy-MOP；2'-(Dicyclohexylphosphino)-[1,1'-binaphthalen]-2-ol；1-(2-dicyclohexylphosphanylnaphthalen-1-yl)naphthalen-2-ol
• CAS: 908293-75-4
• 化学式: C₃₂H₃₅OP
• 分子量: 466.603
• InChiKey: BRTACWKAVFPCTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(dicyclohexylphosphino)-2'-hydroxy-1,1'-binaphthyl 在 三氯硅烷 、 双氧水 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (R)-(+)-2-(dicyclohexylphosphino)-2'-methoxy-1,1'-binaphthyl
  参考文献：
  名称：

  Synthesis of Bulky and Electron-Rich MOP-type Ligands and Their Applications in Palladium-Catalyzed C−N Bond Formation

  摘要：

  A series of 2-dialkylphosphino-2'-alkoxy-1,1'-binaphthyl ligands ( 6a-c and 8a-c) have been prepared conveniently by a lithium-initiated ring-opening reaction of dinaphthofuran, followed by selective phosphorylation. These compounds displayed a remarkable air and moisture stability, both in solid form and in solution. Application of these phosphine ligands in palladium-catalyzed C-N bond forming reactions revealed the crucial roles of the steric bulk of the substituents on the phosphorus atom governing the catalytic activity. Specifically, 2-di-tert-butylphosphino-2'-isopropoxy-1, 1'-binaphthyl ( 8b) proved to be the most effective for the aminations of aryl halides with primary amines, while the less bulky 2-dicyclohexyl-2'-methoxy-1,1'-binaphthyl ( 6a) was more effective for the aminations with secondary amines. The steric and electronic effects of the ligands were analyzed to account for these observations.

  DOI：

  10.1021/jo060945k
• 作为产物：
  描述：

  S-1,1'-联-2-萘酚 在 HY zeolite 、 lithium 作用下， 以 乙醚 、 邻二氯苯 、 甲苯 为溶剂， 反应 8.0h， 生成 2-(dicyclohexylphosphino)-2'-hydroxy-1,1'-binaphthyl
  参考文献：
  名称：

  Synthesis of Bulky and Electron-Rich MOP-type Ligands and Their Applications in Palladium-Catalyzed C−N Bond Formation

  摘要：

  A series of 2-dialkylphosphino-2'-alkoxy-1,1'-binaphthyl ligands ( 6a-c and 8a-c) have been prepared conveniently by a lithium-initiated ring-opening reaction of dinaphthofuran, followed by selective phosphorylation. These compounds displayed a remarkable air and moisture stability, both in solid form and in solution. Application of these phosphine ligands in palladium-catalyzed C-N bond forming reactions revealed the crucial roles of the steric bulk of the substituents on the phosphorus atom governing the catalytic activity. Specifically, 2-di-tert-butylphosphino-2'-isopropoxy-1, 1'-binaphthyl ( 8b) proved to be the most effective for the aminations of aryl halides with primary amines, while the less bulky 2-dicyclohexyl-2'-methoxy-1,1'-binaphthyl ( 6a) was more effective for the aminations with secondary amines. The steric and electronic effects of the ligands were analyzed to account for these observations.

  DOI：

  10.1021/jo060945k

文献信息

• Synthesis of Bulky and Electron-Rich MOP-type Ligands and Their Applications in Palladium-Catalyzed C−N Bond Formation
  作者：Xiaomin Xie、Tony Y. Zhang、Zhaoguo Zhang

  DOI：10.1021/jo060945k

  日期：2006.8.1

  A series of 2-dialkylphosphino-2'-alkoxy-1,1'-binaphthyl ligands ( 6a-c and 8a-c) have been prepared conveniently by a lithium-initiated ring-opening reaction of dinaphthofuran, followed by selective phosphorylation. These compounds displayed a remarkable air and moisture stability, both in solid form and in solution. Application of these phosphine ligands in palladium-catalyzed C-N bond forming reactions revealed the crucial roles of the steric bulk of the substituents on the phosphorus atom governing the catalytic activity. Specifically, 2-di-tert-butylphosphino-2'-isopropoxy-1, 1'-binaphthyl ( 8b) proved to be the most effective for the aminations of aryl halides with primary amines, while the less bulky 2-dicyclohexyl-2'-methoxy-1,1'-binaphthyl ( 6a) was more effective for the aminations with secondary amines. The steric and electronic effects of the ligands were analyzed to account for these observations.