ethyl 4-[5-acetyl-4-(4-fluorophenyl)imidazolyl]piperidinecarboxylate | 186315-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-[5-acetyl-4-(4-fluorophenyl)imidazolyl]piperidinecarboxylate
• 英文别名: 1-(1-Ethoxycarbonyl-4-piperidinyl)-4-(4-fluorophenyl)-5-acetylimidazole；(1-Ethoxycarbonyl-4-piperidinyl)-4-(4-fluorophenyl)-5-acetylimidazole；ethyl 4-[5-acetyl-4-(4-fluorophenyl)imidazol-1-yl]piperidine-1-carboxylate
• CAS: 186315-19-5
• 化学式: C₁₉H₂₂FN₃O₃
• 分子量: 359.4
• InChiKey: ZEOIZHIRWKOEEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  guanidine·HCl 、 N,N-二甲基甲酰胺二甲基缩醛 、 ethyl 4-[5-acetyl-4-(4-fluorophenyl)imidazolyl]piperidinecarboxylate 生成 1-(1-Ethoxycarbonyl-4-piperidinyl)-4-(4-fluorophenyl)-5-(2-(amino)-4-pyrimidinyl)imidazole
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基-1-哌啶甲酸乙酯 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.17h， 生成 ethyl 4-[5-acetyl-4-(4-fluorophenyl)imidazolyl]piperidinecarboxylate
  参考文献：
  名称：

  An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents¹

  摘要：

  This article describes efficient and mild protocols for preparing polysubstituted imidazoles in a single pot fi om aryl-substituted tosylmethyl isocyanide (TosMIC) reagents and imines generated in situ. Traditional imine-forming reactions employing virtually any aldehyde and amine followed by addition of the TosMIC reagent delivers 1,4,5-trisubstituted imidazoles with predictable regiochemistry. Employing chiral amines and aldehydes, particularly those derived from or-amino acids, affords imidazoles with asymmetric centers appended to N-1 or C-5 with excellent retention of chiral purity. 1,4-Disubstituted imidazoles are also readily prepared by a simple variant of the above procedure. Selecting glyoxylic acid as the aldehyde component of this procedure leads to intermediates such as 48, which readily undergo decarboxylation and elimination oft;he tosyl moiety to deliver 1,4-disubstituted imidazoles in high yields. Alternatively, using NH4OH as the amine component in conjunction with a variety of aldehydes delivers 4,5-disubstituted imidazoles in moderate to good yields in a single pot while avoiding the need for protecting groups. Finally, the facile preparation of mono- and disubstituted oxazoles from these TosMIC reagents and aldehydes is described.

  DOI：

  10.1021/jo991782l

文献信息

• Imidazole compounds and compositions
  申请人：SmithKline Beecham Corporation

  公开号：US05739143A1

  公开（公告）日：1998-04-14

  Novel 1,4,5-substituted imidazole compounds and compositions for use in therapy as cytokine inhibitors.

  新型1,4,5-取代咪唑化合物及其在治疗中作为细胞因子抑制剂使用的组合物。
• Imidazole compounds, compositions and use
  申请人：SmithKline Beecham Corporation

  公开号：US05658903A1

  公开（公告）日：1997-08-19

  Novel 1,4,5-substituted imidazole compounds and compositions for use in therapy as cytokine inhibitors.

  1,4,5-取代咪唑化合物及其在治疗中作为细胞因子抑制剂使用的组合物。
• Process for making pyridyl and pyrimidine substituted imidazole compounds
  申请人：SmithKline Beecham Corporation

  公开号：US06218537B1

  公开（公告）日：2001-04-17

  1,4,5,-substituted imidazole compounds and compositions for use in therapy as cytokine inhibitors.

  1,4,5-取代咪唑化合物和组合物，用于作为细胞因子抑制剂的治疗。
• [EN] IMIDAZOLE COMPOUNDS<br/>[FR] COMPOSES D'IMIDAZOLE
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1996040143A1

  公开（公告）日：1996-12-19

  (EN) Novel 1,4,5-substituted imidazole compounds and compositions for use in therapy as cytokine inhibitors.(FR) Nouveaux composés d'imidazole substitués en position 1, 4, 5 et compositions servant d'inhibiteurs de la cytokine à usage thérapeutique.

  (中) 一种1,4,5-取代咪唑化合物和用于治疗的细胞因子抑制剂组成物。
• [EN] NOVEL SYNTHESIS<br/>[FR] NOUVELLE SYNTHESE
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1997023479A1

  公开（公告）日：1997-07-03

  (EN) The present invention relates to a novel method for synthesizing imidazole derivatives having 4-aryl, 5-pyrimidine heterocyclic rings using a novel cycloaddition reaction.(FR) Nouveau procédé de synthèse de dérivés d'imidazole comportant des cycles hétérocycliques 4-aryle, 5-pyrimidine, à l'aide d'une nouvelle réaction de cycloaddition.

  （中文）本发明涉及一种新型环加成反应合成4-芳基、5-嘧啶杂环环的咪唑衍生物的方法。