4,5-dimethyl-3(4-trimethoxysilylphenylmethyl)thiazolium chloride | 1186520-86-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4,5-dimethyl-3(4-trimethoxysilylphenylmethyl)thiazolium chloride
• CAS: 1186520-86-4
• 化学式: C₁₅H₂₂NO₃SSi*Cl
• 分子量: 359.949
• InChiKey: NCBQOQSPWGCVRM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.21
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  31.57
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4,5-二甲基噻唑 、 4-(氯甲基)苯基三甲氧基硅烷 以 乙腈 为溶剂， 反应 24.0h， 以100%的产率得到4,5-dimethyl-3(4-trimethoxysilylphenylmethyl)thiazolium chloride
  参考文献：
  名称：

  Sustainable, green protocols for heterogenized organocatalysts: N-Phenylthiazolium salts heterogenized on organic–inorganic hybrid mesoporous supports

  摘要：

  A heterogenized organocatalyst was synthesized by the covalent anchoring of N-phenyl-thiazolium salts over mesoporous organosilica (phenylene-silica, ethane-silica) and mesoporous silica (MCM-41) supports. Powder X-ray diffraction patterns as well as nitrogen physisorption analysis confirmed the retention of mesoporous structure after the grafting reactions. Solid-state NMR analysis (C-13 CP-MAS NMR, Si-29 MAS NMR) certified the integrity of organocatalyst residing inside the pore channels of the mesoporous supports. Catalytic evaluation in the benzoin condensation reaction as well as in the cross-coupling of aldehydes with acyl imines indicated that the organocatalyst heterogenized on mesoporous phenylene organosilica exhibited higher catalytic activity, stability and reusability than the analogous mesoporous silica support. The better activity and stability of the phenylene-silica support was attributed to the enhanced hydrophobic properties arising from the frame wall organic groups. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.08.022
• 作为试剂：
  描述：

  4-吡啶甲醛 、 N-(α-tosylbenzyl)-cyclohexanecarboxamide 在 4,5-dimethyl-3(4-trimethoxysilylphenylmethyl)thiazolium chloride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到N-(2-oxo-1-phenyl-2-(pyridin-4-yl)-ethyl)-cyclohexanecarboxamide
  参考文献：
  名称：

  Sustainable, green protocols for heterogenized organocatalysts: N-Phenylthiazolium salts heterogenized on organic–inorganic hybrid mesoporous supports

  摘要：

  A heterogenized organocatalyst was synthesized by the covalent anchoring of N-phenyl-thiazolium salts over mesoporous organosilica (phenylene-silica, ethane-silica) and mesoporous silica (MCM-41) supports. Powder X-ray diffraction patterns as well as nitrogen physisorption analysis confirmed the retention of mesoporous structure after the grafting reactions. Solid-state NMR analysis (C-13 CP-MAS NMR, Si-29 MAS NMR) certified the integrity of organocatalyst residing inside the pore channels of the mesoporous supports. Catalytic evaluation in the benzoin condensation reaction as well as in the cross-coupling of aldehydes with acyl imines indicated that the organocatalyst heterogenized on mesoporous phenylene organosilica exhibited higher catalytic activity, stability and reusability than the analogous mesoporous silica support. The better activity and stability of the phenylene-silica support was attributed to the enhanced hydrophobic properties arising from the frame wall organic groups. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.08.022