4-[[1-[(1,1-二甲基乙氧基)羰基]-1H-咪唑-4-基]羰基]-1-哌啶羧酸叔丁酯 | 639089-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-[[1-[(1,1-二甲基乙氧基)羰基]-1H-咪唑-4-基]羰基]-1-哌啶羧酸叔丁酯
• 英文名称: 4-(1-tert-butoxycarbonyl-1H-imidazol-4-carbonyl)piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-(1-(tert-butoxycarbonyl)-1H-imidazole-4-carbonyl)piperidine-1-carboxylate；tert-butyl 4-[1-[(2-methylpropan-2-yl)oxycarbonyl]imidazole-4-carbonyl]piperidine-1-carboxylate
• CAS: 639089-44-4
• 化学式: C₁₉H₂₉N₃O₅
• 分子量: 379.456
• InChiKey: FPIFWACOAYGZQP-UHFFFAOYSA-N

物化性质

• 沸点：
  500.5±60.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  90.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[[1-[(1,1-二甲基乙氧基)羰基]-1H-咪唑-4-基]羰基]-1-哌啶羧酸叔丁酯 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以100%的产率得到VUF 5464
  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：

  (1H-imidazol-5-yl)piperidin-4-ylmethanol dihydrogen chloride 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.75h， 生成 4-[[1-[(1,1-二甲基乙氧基)羰基]-1H-咪唑-4-基]羰基]-1-哌啶羧酸叔丁酯
  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

文献信息

• Synthesis and Structure−Activity Relationships of Conformationally Constrained Histamine H₃ Receptor Agonists
  作者：Ruengwit Kitbunnadaj、Obbe P. Zuiderveld、Iwan J. P. De Esch、Roeland C. Vollinga、Remko Bakker、Martin Lutz、Anthony L. Spek、Emile Cavoy、Marie-France Deltent、Wiro M. P. B. Menge、Henk Timmerman、Rob Leurs

  DOI：10.1021/jm030905y

  日期：2003.12.1

  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.