3-[2-[(4-Methoxyphenyl)methoxy]pyrimidin-4-yl]-5-propan-2-yloxyphenol | 1448788-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-[2-[(4-Methoxyphenyl)methoxy]pyrimidin-4-yl]-5-propan-2-yloxyphenol
• 英文别名: 3-[2-[(4-methoxyphenyl)methoxy]pyrimidin-4-yl]-5-propan-2-yloxyphenol
• CAS: 1448788-50-8
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: ZFZFCPYCLFYMMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[2-[(4-Methoxyphenyl)methoxy]pyrimidin-4-yl]-5-propan-2-yloxyphenol 在 potassium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 6-[3-(4-methylsulfonylphenoxy)-5-propan-2-yloxyphenyl]-1H-pyrimidin-2-one
  参考文献：
  名称：

  Pyrimidone-based series of glucokinase activators with alternative donor–acceptor motif

  摘要：

  Glucokinase activators are a class of experimental agents under investigation as a therapy for Type 2 diabetes mellitus. An X-ray crystal structure of a modestly potent agent revealed the potential to substitute the common heterocyclic amide donor-acceptor motif for a pyridone moiety. We have successfully demonstrated that both pyridone and pyrimidone heterocycles can be used as a potent donor-acceptor substituent. Several sub-micromolar analogs that possess the desired partial activator profile were synthesized and characterized. Unfortunately, the most potent activators suffered from sub-optimal pharmacokinetic properties. Nonetheless, these donor-acceptor motifs may find utility in other glucokinase activator series or beyond. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.036
• 作为产物：
  描述：

  tert-butyl(3-isopropoxyphenoxy)dimethylsilane 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 四丁基氟化铵 、 sodium carbonate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 甲基叔丁基醚 、 水 为溶剂， 反应 24.0h， 生成 3-[2-[(4-Methoxyphenyl)methoxy]pyrimidin-4-yl]-5-propan-2-yloxyphenol
  参考文献：
  名称：

  Pyrimidone-based series of glucokinase activators with alternative donor–acceptor motif

  摘要：

  Glucokinase activators are a class of experimental agents under investigation as a therapy for Type 2 diabetes mellitus. An X-ray crystal structure of a modestly potent agent revealed the potential to substitute the common heterocyclic amide donor-acceptor motif for a pyridone moiety. We have successfully demonstrated that both pyridone and pyrimidone heterocycles can be used as a potent donor-acceptor substituent. Several sub-micromolar analogs that possess the desired partial activator profile were synthesized and characterized. Unfortunately, the most potent activators suffered from sub-optimal pharmacokinetic properties. Nonetheless, these donor-acceptor motifs may find utility in other glucokinase activator series or beyond. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.036