(S)-5-((tert-butyldiphenylsilyloxy)methyl)-2-(4-fluorophenyl)-6,7-dihydro-5Hpyrrolo[1,2-a]imidazole | 926659-97-4

• 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)-5-((tert-butyldiphenylsilyloxy)methyl)-2-(4-fluorophenyl)-6,7-dihydro-5Hpyrrolo[1,2-a]imidazole
• 英文别名: tert-butyl-[[(5S)-2-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-5-yl]methoxy]-diphenylsilane
• CAS: 926659-97-4
• 化学式: C₂₉H₃₁FN₂OSi
• 分子量: 470.662
• InChiKey: KAOGZVHKJLLNAR-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  (S)-5-((tert-butyldiphenylsilyloxy)methyl)-2-(4-fluorophenyl)-6,7-dihydro-5Hpyrrolo[1,2-a]imidazole 在 sodium hydroxide 、 四丁基氟化铵 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 (5S)-2-(4-fluorophenyl)-5-[(4-methoxyphenyl)methoxymethyl]-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
  参考文献：
  名称：

  The neuroprotective action of JNK3 inhibitors based on the 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold

  摘要：

  Imidazole-based structures of p38 inhibitors served as a starting point for the design of JNK3 inhibitors. Construction of a 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold led to the synthesis of the (S)-enantiomers, which exhibited p38/JNK3 IC50 ratio of up to 10 and were up to 20 times more potent inhibitors of JNK3 than the relevant (R)-enantiomers. The JNK3 inhibitory potency correlated well with inhibition of c-Jun phosphorylation and neuroprotective properties of the compounds in low K+-induced cell death of rat cerebellar granule neurotics. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.076
• 作为产物：
  描述：

  (S)-5-[(tert-butyl)-diphenylsilyloxy-methyl]-2-thiopyrrolidinone 在 氢溴酸 、 氯化铵 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 30.0h， 生成 (S)-5-((tert-butyldiphenylsilyloxy)methyl)-2-(4-fluorophenyl)-6,7-dihydro-5Hpyrrolo[1,2-a]imidazole
  参考文献：
  名称：

  The neuroprotective action of JNK3 inhibitors based on the 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold

  摘要：

  Imidazole-based structures of p38 inhibitors served as a starting point for the design of JNK3 inhibitors. Construction of a 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold led to the synthesis of the (S)-enantiomers, which exhibited p38/JNK3 IC50 ratio of up to 10 and were up to 20 times more potent inhibitors of JNK3 than the relevant (R)-enantiomers. The JNK3 inhibitory potency correlated well with inhibition of c-Jun phosphorylation and neuroprotective properties of the compounds in low K+-induced cell death of rat cerebellar granule neurotics. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.076

文献信息

• Regio- and Enantioselective <i>N</i>-Allylations of Imidazole, Benzimidazole, and Purine Heterocycles Catalyzed by Single-Component Metallacyclic Iridium Complexes
  作者：Levi M. Stanley、John F. Hartwig

  DOI：10.1021/ja902243s

  日期：2009.7.1

  Kinetic studies on the allylation of benzimidazole catalyzed by metallacyclic iridium-phosphoramidite complexes, in combination with studies on the deactivation of these catalysts in the presence of heterocyclic nucleophiles, provide insight into the effects of the structures of the phosphoramidite ligands on the stability of the metallacyclic catalysts. The data obtained from these studies have led to

  已经开发出高度区域选择性和对映选择性铱催化的苯并咪唑、咪唑和嘌呤的 N-烯丙基化反应。N-烯丙基化苯并咪唑和咪唑从苯并咪唑和咪唑亲核试剂与在单组分乙烯键合金属环铱催化剂存在下的不对称烯丙基碳酸酯。还以高 N9/N7 选择性（高达 96:4）、高支链到线性选择性（98:2）和高对映选择性（高达 98 % ee) 在类似条件下。这些反应包括一系列苯并咪唑、咪唑和嘌呤亲核试剂，以及各种不对称芳基、杂芳基、和脂肪族烯丙基碳酸酯。在这项工作中研究的常见胺亲核试剂和杂环氮亲核试剂之间的竞争实验说明了亲核试剂 pK(a) 对铱催化 N-烯丙基化反应速率的影响。金属环铱-亚磷酰胺配合物催化苯并咪唑烯丙基化的动力学研究，结合在杂环亲核试剂存在下对这些催化剂失活的研究，深入了解亚磷酰胺配体的结构对金属环稳定性的影响催化剂。从这些研究中获得的数据导致苯并咪唑和咪唑在没有外源碱的情况下的 N-烯丙基化的发展。在这
• 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.