[4-(1-Methylimidazol-2-yl)phenyl]-diphenylphosphane | 385442-13-7

• 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: [4-(1-Methylimidazol-2-yl)phenyl]-diphenylphosphane
• CAS: 385442-13-7
• 化学式: C₂₂H₁₉N₂P
• 分子量: 342.38
• InChiKey: BPVSUZHYUUPXHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [4-(1-Methylimidazol-2-yl)phenyl]-diphenylphosphane 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以45%的产率得到2-(4-Diphenylphosphanyl-phenyl)-1-methyl-3H-imidazol-1-ium; chloride
  参考文献：
  名称：

  Phosphines with 2-imidazolium and para-phenyl-2-imidazolium moieties—synthesis and application in two-phase catalysis

  摘要：

  Deprotonation of 1-n-butyl-3-methyl-imidazolium chloride or hexafluorophosphate with n-butyl lithium and subsequent reaction of the intermediate 2,3-dihydro-imidazol-2-ylidene with diphenylchlorophosphine affords the 2-imidazolium phosphines 3a or 3b. The phosphine 4 with a para-phenylene spacer between the imidazolyl moiety and the phosphorus atom has been obtained by Kosugi-Stille coupling between 2-tri-n-butyl-stannyl-1-methylimidazole and 4-fluoroiodobenzene followed by nucleophilic substitution of fluorine with PPh2K. The X-ray structure of 4 (space group P1) has been determined. Selective N-protonation or N-quaternization of 4 affords the corresponding imidazolium phosphines 5a-5c. The ligands 3b and 5c have been tested in the biphasic Rh-catalyzed hydroformylation of 1-octene employing the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate as catalyst solvent. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00868-3
• 作为产物：
  描述：

  对氟碘苯 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 101.0h， 生成 [4-(1-Methylimidazol-2-yl)phenyl]-diphenylphosphane
  参考文献：
  名称：

  Phosphines with 2-imidazolium and para-phenyl-2-imidazolium moieties—synthesis and application in two-phase catalysis

  摘要：

  Deprotonation of 1-n-butyl-3-methyl-imidazolium chloride or hexafluorophosphate with n-butyl lithium and subsequent reaction of the intermediate 2,3-dihydro-imidazol-2-ylidene with diphenylchlorophosphine affords the 2-imidazolium phosphines 3a or 3b. The phosphine 4 with a para-phenylene spacer between the imidazolyl moiety and the phosphorus atom has been obtained by Kosugi-Stille coupling between 2-tri-n-butyl-stannyl-1-methylimidazole and 4-fluoroiodobenzene followed by nucleophilic substitution of fluorine with PPh2K. The X-ray structure of 4 (space group P1) has been determined. Selective N-protonation or N-quaternization of 4 affords the corresponding imidazolium phosphines 5a-5c. The ligands 3b and 5c have been tested in the biphasic Rh-catalyzed hydroformylation of 1-octene employing the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate as catalyst solvent. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00868-3