1-(2,6-diisopropylphenyl)-3-tert-butylimidazolium-2-carboxylate | 1188360-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,6-diisopropylphenyl)-3-tert-butylimidazolium-2-carboxylate
• 英文别名: 1-Tert-butyl-3-[2,6-di(propan-2-yl)phenyl]imidazol-1-ium-2-carboxylate
• CAS: 1188360-00-0
• 化学式: C₂₀H₂₈N₂O₂
• 分子量: 328.455
• InChiKey: IYICTGGMRYVCQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二氧化碳 、 1-tert-butyl-3-(2,6-diisopropyl)phenyl-imidazolium tetrafluoroborate 在 双(三甲基硅烷基)氨基钾 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以87%的产率得到1-(2,6-diisopropylphenyl)-3-tert-butylimidazolium-2-carboxylate
  参考文献：
  名称：

  A Systematic Investigation of Factors Influencing the Decarboxylation of Imidazolium Carboxylates

  摘要：

  A series of 1,3-disubstituted-2-imidazolium carboxylates, an adduct of CO2 and N-heterocyclic carbenes, were synthesized and characterized using single crystal X-ray, thermogravimetric, IR, and NMR analysis. The TGA analysis of the NHC-CO2's shows that as steric bulk on the N-substituent increases, the ability of the NHC-CO2 to decarboxylate increases. The comparison of NHC-CO2's with and without methyls at the 4,5-position indicate that extra electron density in the imidazolium ring enhances the stability of an NHC-CO2 thereby making it less prone to decarboxylation. Single crystal X-ray analysis shows that the torsional angle of the carboxylate group and the C-CO2 bond length with respect to the imidazolium ring is dependent on the steric bulk of the N-substituent. Rotamers in the unit cell of a single crystal of I'BuPrCO2 (2f) indicate that the C-CO2 bond length increases as the N-substituents rotate toward the carboxylate moiety, which suggests that rotation of the N-substituents through the plane of the C-CO2 bond may be involved in the bond breaking event to release CO2.

  DOI：

  10.1021/jo901791k