2-(3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-yl)acetate | 1448750-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-yl)acetate
• CAS: 1448750-33-1
• 化学式: C₁₀H₁₆N₂O₂
• 分子量: 196.249
• InChiKey: NKBYNVLQXGRKAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  48.94
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-叔丁基-1H-咪唑 在 正丁基锂 、 potassium hydride 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， -78.0~40.0 ℃ 、101.33 kPa 条件下， 反应 53.17h， 生成 2-(3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-yl)acetate
  参考文献：
  名称：

  Fast CO₂ Sequestration, Activation, and Catalytic Transformation Using N-Heterocyclic Olefins

  摘要：

  N-Heterocyclic Olefin (NHO) with high electronegativity at the terminal carbon atom was found to show a strong tendency for CO2 sequestration, affording a CO2 adduct (NHO-CO2). X-ray single crystal analysis revealed the bent geometry of the binding CO2 in the NHO-CO2 adducts with an O-C-O angle of 127.7-129.9 degrees, dependent on the substitute groups of N-heterocyclic ring. The length of the C-carboxylate-C-NHO bond is in the range of 1.55-1.57 angstrom, significantly longer than that of the C-carboxylate-C-NHC bond (1.52-1.53 angstrom) of the previously reported NHC-CO2 adducts. The FTIR study by monitoring the v(CO2) region of transmittance change demonstrated that the decarboxylation of NHO-CO2 adducts is easier than that of the corresponding NHC-CO2 adducts. Notably, the NHO-CO2 adducts were found to be highly active in catalyzing the carboxylative cyclization of CO2 and propargylic alcohols at mild conditions (even at ambient temperature and 0.1 MPa CO2 pressure), selectively giving alpha-alkylidene cyclic carbonates in good yields. The catalytic activity is about 10-200 times that of the corresponding NHC-CO2 adducts at the same conditions. Two reaction paths regarding the hydrogen at the alkenyl position of cyclic carbonates coming from substrate (path A) or both substrate and catalyst (path B) were proposed on the basis of deuterium labeling experiments. The high activity of NHO-CO2 adduct was tentatively ascribed to its low stability for easily releasing the CO2 moiety and/or the desired product, a possible rate-limiting step in the catalytic cycle.

  DOI：

  10.1021/ja405114e