3-(3-acetoxypropyl)-1-methyl-1H-imidazol-3-ium chloride | 1435484-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3-acetoxypropyl)-1-methyl-1H-imidazol-3-ium chloride
• CAS: 1435484-02-8
• 化学式: C₉H₁₅N₂O₂*Cl
• 分子量: 218.683
• InChiKey: OGBTZKSMHVHUFW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.73
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.11
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 3-(3-acetoxypropyl)-1-methyl-1H-imidazol-3-ium chloride 在 silver(l) oxide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 72.0h， 以61%的产率得到IrCl(1,5-cyclooctadiene)(MeIm(CH₂)₃OCOCH₃)
  参考文献：
  名称：

  Enhanced Hydrogen-Transfer Catalytic Activity of Iridium N-Heterocyclic Carbenes by Covalent Attachment on Carbon Nanotubes

  摘要：

  Oxidized multiwall carbon nanotubes (CNT) were covalently modified with appropriate hydroxyl-ending imidazolium salts using their carboxylic acid groups. Characterization of the imidazolium-modified samples through typical solid characterization techniques, such as TGA or XPS, allows for the determination of 16 wt % in CNT-1 and 31 wt % in CNT-2 as the amount of the imidazolic fragments in the carbon nanotubes. The imidazolium-functionalized materials were used to prepare nanohybrid materials containing iridium N-heterocyclic carbene (NHC)-type organometallic complexes with efficiencies as high as 95%. The nanotube-supported iridium-NHC materials were active in the heterogeneous iridium-catalyzed hydrogen-transfer reduction of cyclohexanone to cyclohexanol with 2-propanol/KOH as hydrogen source. The iridium hybrid materials are more efficient than related homogeneous catalysts based on acetoxy-functionalized Ir-NHC complexes with initial TOFs up to 5550 h(-1). A good recyclability of the catalysts, without any loss of activity, and stability in air was observed.

  DOI：

  10.1021/cs4000798
• 作为产物：
  描述：

  N-甲基咪唑 、 3-氯丙基乙酸酯 以 乙腈 为溶剂， 反应 72.0h， 以83%的产率得到3-(3-acetoxypropyl)-1-methyl-1H-imidazol-3-ium chloride
  参考文献：
  名称：

  Enhanced Hydrogen-Transfer Catalytic Activity of Iridium N-Heterocyclic Carbenes by Covalent Attachment on Carbon Nanotubes

  摘要：

  Oxidized multiwall carbon nanotubes (CNT) were covalently modified with appropriate hydroxyl-ending imidazolium salts using their carboxylic acid groups. Characterization of the imidazolium-modified samples through typical solid characterization techniques, such as TGA or XPS, allows for the determination of 16 wt % in CNT-1 and 31 wt % in CNT-2 as the amount of the imidazolic fragments in the carbon nanotubes. The imidazolium-functionalized materials were used to prepare nanohybrid materials containing iridium N-heterocyclic carbene (NHC)-type organometallic complexes with efficiencies as high as 95%. The nanotube-supported iridium-NHC materials were active in the heterogeneous iridium-catalyzed hydrogen-transfer reduction of cyclohexanone to cyclohexanol with 2-propanol/KOH as hydrogen source. The iridium hybrid materials are more efficient than related homogeneous catalysts based on acetoxy-functionalized Ir-NHC complexes with initial TOFs up to 5550 h(-1). A good recyclability of the catalysts, without any loss of activity, and stability in air was observed.

  DOI：

  10.1021/cs4000798