(S)-1-(1-hydroxy-3-methylbutan-2-yl)-3-(2,4,6-trimethylbenzyl)-1H-imidazol-3-ium bromide | 1619981-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-1-(1-hydroxy-3-methylbutan-2-yl)-3-(2,4,6-trimethylbenzyl)-1H-imidazol-3-ium bromide
• CAS: 1619981-52-0
• 化学式: Br*C₁₈H₂₇N₂O
• 分子量: 367.329
• InChiKey: UOVHMWUEZNMZKC-GMUIIQOCSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.04
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(1-hydroxy-3-methylbutan-2-yl)-3-(2,4,6-trimethylbenzyl)-1H-imidazol-3-ium bromide 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 在 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以53%的产率得到C₂₆H₃₇N₂ORh
  参考文献：
  名称：

  Chelating alkoxy NHC–Rh(I) complexes and their applications in the arylation of aldehydes

  摘要：

  In this study, new rhodium(I) complexes (5 and 6) have been prepared by the reaction of [RhCI(COD)](2) with a series of imidazolium salts (3 and 4), which were obtained from a chiral amino alcohol. The catalytic activities of these complexes were tested in the arylation of aldehydes. It was found that the synthesized rhodium complexes were highly effective catalysts for the arylation of aldehydes in short reaction times (5 mm, TOF = 1193 h(-1)). However, the obtained ee values (up to 32% ee) remained low. We have proposed a mechanism for the arylation reaction of aldehydes, which is confirmed via F-19 NMR spectroscopy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.125
• 作为产物：
  描述：

  2,4,6-三甲基溴化苄 、 1-[(2S)-1-methoxy-3-methylbutan-2-yl]-1H-imidazole 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以90%的产率得到(S)-1-(1-hydroxy-3-methylbutan-2-yl)-3-(2,4,6-trimethylbenzyl)-1H-imidazol-3-ium bromide
  参考文献：
  名称：

  Chelating alkoxy NHC–Rh(I) complexes and their applications in the arylation of aldehydes

  摘要：

  In this study, new rhodium(I) complexes (5 and 6) have been prepared by the reaction of [RhCI(COD)](2) with a series of imidazolium salts (3 and 4), which were obtained from a chiral amino alcohol. The catalytic activities of these complexes were tested in the arylation of aldehydes. It was found that the synthesized rhodium complexes were highly effective catalysts for the arylation of aldehydes in short reaction times (5 mm, TOF = 1193 h(-1)). However, the obtained ee values (up to 32% ee) remained low. We have proposed a mechanism for the arylation reaction of aldehydes, which is confirmed via F-19 NMR spectroscopy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.125