4-[(1-tert-butoxycarbonyl-1H-imidazol-4-yl)hydroxymethyl]piperidine-1-carboxylic acid tert-butyl ester | 639089-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-[(1-tert-butoxycarbonyl-1H-imidazol-4-yl)hydroxymethyl]piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-((1-(tert-butoxycarbonyl)-1H-imidazol-4-YL)(hydroxy)methyl)piperidine-1-carboxylate；tert-butyl 4-[hydroxy-[1-[(2-methylpropan-2-yl)oxycarbonyl]imidazol-4-yl]methyl]piperidine-1-carboxylate
• CAS: 639089-41-1
• 化学式: C₁₉H₃₁N₃O₅
• 分子量: 381.472
• InChiKey: UDGYTBIHNVKMNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  93.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(1-tert-butoxycarbonyl-1H-imidazol-4-yl)hydroxymethyl]piperidine-1-carboxylic acid tert-butyl ester 在 盐酸 、 三乙胺 、 calcium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 VUF 5510
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Conformationally Constrained Histamine H₃ Receptor Agonists

  摘要：

  Immepip, a conformationally constrained analogue of the histamine congener imbutamine, shows high affinity and functional activity on the human H-3 receptor. Using histamine and its homologues as prototypes, other rigid analogues containing either a piperidine or pyrrolidine ring in the side chain were synthesized and tested for their activities at the human H-3 receptor and the closely related H-4 receptor. In the series of piperidine containing analogues, immepip was found to be the most potent H-3 receptor agonist, whereas its propylene analogue 13a was identified as a high-affinity neutral antagonist for the human H-3 receptor. Moreover, replacement of the piperidine ring of immepip by a pyrrolidine ring led to a pair of enantiomers that show a distinct stereoselectivity at the human H-3 and H-4 receptor.

  DOI：

  10.1021/jm030905y
• 作为产物：
  描述：

  4-吡啶甲醛 在 palladium on activated charcoal 、 Rh on carbon 盐酸 、 乙基溴化镁 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、10.13 MPa 条件下， 反应 88.75h， 生成 4-[(1-tert-butoxycarbonyl-1H-imidazol-4-yl)hydroxymethyl]piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Conformationally Constrained Histamine H₃ Receptor Agonists

  摘要：

  Immepip, a conformationally constrained analogue of the histamine congener imbutamine, shows high affinity and functional activity on the human H-3 receptor. Using histamine and its homologues as prototypes, other rigid analogues containing either a piperidine or pyrrolidine ring in the side chain were synthesized and tested for their activities at the human H-3 receptor and the closely related H-4 receptor. In the series of piperidine containing analogues, immepip was found to be the most potent H-3 receptor agonist, whereas its propylene analogue 13a was identified as a high-affinity neutral antagonist for the human H-3 receptor. Moreover, replacement of the piperidine ring of immepip by a pyrrolidine ring led to a pair of enantiomers that show a distinct stereoselectivity at the human H-3 and H-4 receptor.

  DOI：

  10.1021/jm030905y