rac-(1R,5R,8R)-isopropyl 8-(5-methyl-6-(2-methylpyridin-3-yloxy)pyrimidin-4-yloxy)-6-oxa-3-azabicyclo[3.2.1]octane-3-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-(1R,5R,8R)-isopropyl 8-(5-methyl-6-(2-methylpyridin-3-yloxy)pyrimidin-4-yloxy)-6-oxa-3-azabicyclo[3.2.1]octane-3-carboxylate
• 英文别名: (1R,5R,8R)-Isopropyl 8-(5-Methyl-6-(2-methylpyridin-3-yloxy)pyrimidin-4-yloxy)-6-oxa-3-azabicyclo[3.2.1]octane-3-carboxylate；propan-2-yl (1R,5R,8R)-8-[5-methyl-6-(2-methylpyridin-3-yl)oxypyrimidin-4-yl]oxy-6-oxa-3-azabicyclo[3.2.1]octane-3-carboxylate
• 化学式: C₂₁H₂₆N₄O₅
• 分子量: 414.461
• InChiKey: CUSGJPDCMHXABC-KBAYOESNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-氯-5-甲基-6-((2-甲基吡啶-3-基)氧基)嘧啶 、 在 lithium hexamethyldisilazane 作用下， 以 1,4-二氧六环 为溶剂， 反应 17.0h， 以52%的产率得到rac-(1R,5R,8R)-isopropyl 8-(5-methyl-6-(2-methylpyridin-3-yloxy)pyrimidin-4-yloxy)-6-oxa-3-azabicyclo[3.2.1]octane-3-carboxylate
  参考文献：
  名称：

  Activation of the G-Protein-Coupled Receptor 119: A Conformation-Based Hypothesis for Understanding Agonist Response

  摘要：

  The synthesis and properties of the bridged piperidine (oxaazabicyclo) compounds 8, 9, and 11 are described. A conformational analysis of these structures is compared with the representative GPR119 ligand 1. These results and the differences in agonist pharmacology are used to formulate a conformation-based hypothesis to understand activation of the GPR119 receptor. We also show for these structures that the agonist pharmacology in rat masks the important differences in human pharmacology.

  DOI：

  10.1021/jm200003p