(5S,7S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-fluoro-phenyl)-7-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole | 926660-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5S,7S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-fluoro-phenyl)-7-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
• 英文别名: tert-butyl-[[(5S,7S)-2-(4-fluorophenyl)-7-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-5-yl]methoxy]-diphenylsilane
• CAS: 926660-05-1
• 化学式: C₃₀H₃₃FN₂OSi
• 分子量: 484.689
• InChiKey: XLRWPMWUYIAZPK-DHLKQENFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (5S,7S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-fluoro-phenyl)-7-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole 在 Pd₂(dibenzylideneacetone)2*CHCl₃ Oxone 、 copper(l) iodide 、 溴 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 28.25h， 生成 {4-[5-(tert-butyldiphenylsilanyloxymethyl)-2-(4-fluorophenyl)-7-methyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl]-pyrimidin-2-yl}-propylamine
  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-[4-(4-fluorophenyl)-imidazol-1-yl]-pent-4-en-1-ol 在 [RhCl(coe)2]2 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 magnesium bromide 、 三环己基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 (5S,7S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-fluoro-phenyl)-7-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

文献信息

• Synthesis of Potent Bicyclic Bisarylimidazole c-Jun N-Terminal Kinase Inhibitors by Catalytic C−H Bond Activation
  作者：Jason C. Rech、Michihisa Yato、Derek Duckett、Brian Ember、Philip V. LoGrasso、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ja0676004

  日期：2007.1.1

  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.