1-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-allyl]-4-(4-fluoro-phenyl)-1H-imidazole | 926660-00-6

• 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-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-allyl]-4-(4-fluoro-phenyl)-1H-imidazole
• 英文别名: tert-butyl-[(2S)-2-[4-(4-fluorophenyl)imidazol-1-yl]-3-methylbut-3-enoxy]-diphenylsilane
• CAS: 926660-00-6
• 化学式: C₃₀H₃₃FN₂OSi
• 分子量: 484.689
• InChiKey: ZKNUZWCXBHALJW-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-allyl]-4-(4-fluoro-phenyl)-1H-imidazole 在 [RhCl(coe)2]2 溴 、 magnesium bromide 、 三环己基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 40.25h， 生成 3-bromo-5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-6-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
  参考文献：
  名称：

  Synthesis of Potent Bicyclic Bisarylimidazole c-Jun N-Terminal Kinase Inhibitors by Catalytic C−H Bond Activation

  摘要：

  The efficient preparation of the privileged bicyclic bisarylimidazole kinase inhibitor scaffold was accomplished using rhodium-catalyzed C-H activation and intramolecular alkylation. The key C-H activation/alkylation step represents one of the first evaluations of diastereocontrol in catalyzed C-H activation/olefin alkylation processes. Several inhibitors of JNK3 were prepared using this sequence, with the most potent inhibitor having an IC50 value of 1.6 nM.

  DOI：

  10.1021/ja0676004
• 作为产物：
  描述：

  (S)-2-Amino-3-methyl-but-3-en-1-ol; hydrochloride 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 1-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-allyl]-4-(4-fluoro-phenyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis of Potent Bicyclic Bisarylimidazole c-Jun N-Terminal Kinase Inhibitors by Catalytic C−H Bond Activation

  摘要：

  The efficient preparation of the privileged bicyclic bisarylimidazole kinase inhibitor scaffold was accomplished using rhodium-catalyzed C-H activation and intramolecular alkylation. The key C-H activation/alkylation step represents one of the first evaluations of diastereocontrol in catalyzed C-H activation/olefin alkylation processes. Several inhibitors of JNK3 were prepared using this sequence, with the most potent inhibitor having an IC50 value of 1.6 nM.

  DOI：

  10.1021/ja0676004