tert-butyl N-[(tert-butoxy)carbonyl]-N-[(1S,5S,6R)-2-oxo-1-propyl-3-oxabicyclo[4.1.0]heptan-5-yl]carbamate | 1431611-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tert-butyl N-[(tert-butoxy)carbonyl]-N-[(1S,5S,6R)-2-oxo-1-propyl-3-oxabicyclo[4.1.0]heptan-5-yl]carbamate
• 英文别名: tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-[(1S,5S,6R)-2-oxo-1-propyl-3-oxabicyclo[4.1.0]heptan-5-yl]carbamate
• CAS: 1431611-21-0
• 化学式: C₁₉H₃₁NO₆
• 分子量: 369.458
• InChiKey: QFAAVKJCSPWCLE-QUJCMNEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(tert-butoxy)carbonyl]-N-[(1S,5S,6R)-2-oxo-1-propyl-3-oxabicyclo[4.1.0]heptan-5-yl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以95%的产率得到tert-butyl ((1S,5S,6R)-2-oxo-1-propyl-3-oxabicyclo[4.1.0]heptan-5-yl)carbamate
  参考文献：
  名称：

  Development of 2′-Substituted (2S,1′R,2′S)-2-(Carboxycyclopropyl)glycine Analogues as Potent N-Methyl-d-aspartic Acid Receptor Agonists

  摘要：

  A series of 2'-substituted analogues of the selective NMDA receptor ligand (2S,1'R,2'S)-2-(carboxycyclopropyl)glycine ((S)-CCG-IV) have been designed, synthesized, and pharmacologically characterized. The design was based on a docking study hypothesizing that substituents in the 2'-position would protrude into a region where differences among the NMDA receptor GluN2 subunits exist. Various synthetic routes were explored, and two different routes provided a series of alkyl-substituted analogues. Pharmacological characterization revealed that these compounds are NMDA receptor agonists and that potency decreases with increasing size of the alkyl groups. Variations in agonist activity are observed at the different recombinant NMDA receptor subtypes. This study demonstrates that it is possible to introduce substituents in the 2'-position of (S)-CCG-IV while maintaining agonist activity and that variation among NMDA receptor subtypes may be achieved by probing this region of the receptor.

  DOI：

  10.1021/jm400346a
• 作为产物：
  描述：

  (4S)-1,1-dimethylethyl 4-<(Z)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate 在 吡啶 、 4-二甲氨基吡啶 、 碘 、 palladium diacetate 、 三氟乙酸 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 52.5h， 生成 tert-butyl N-[(tert-butoxy)carbonyl]-N-[(1S,5S,6R)-2-oxo-1-propyl-3-oxabicyclo[4.1.0]heptan-5-yl]carbamate
  参考文献：
  名称：

  Development of 2′-Substituted (2S,1′R,2′S)-2-(Carboxycyclopropyl)glycine Analogues as Potent N-Methyl-d-aspartic Acid Receptor Agonists

  摘要：

  A series of 2'-substituted analogues of the selective NMDA receptor ligand (2S,1'R,2'S)-2-(carboxycyclopropyl)glycine ((S)-CCG-IV) have been designed, synthesized, and pharmacologically characterized. The design was based on a docking study hypothesizing that substituents in the 2'-position would protrude into a region where differences among the NMDA receptor GluN2 subunits exist. Various synthetic routes were explored, and two different routes provided a series of alkyl-substituted analogues. Pharmacological characterization revealed that these compounds are NMDA receptor agonists and that potency decreases with increasing size of the alkyl groups. Variations in agonist activity are observed at the different recombinant NMDA receptor subtypes. This study demonstrates that it is possible to introduce substituents in the 2'-position of (S)-CCG-IV while maintaining agonist activity and that variation among NMDA receptor subtypes may be achieved by probing this region of the receptor.

  DOI：

  10.1021/jm400346a