2,2-dimethyl-6-(oxiran-2-ylmethoxy)-4H-benzo[d][1,3]dioxine | 1279016-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2,2-dimethyl-6-(oxiran-2-ylmethoxy)-4H-benzo[d][1,3]dioxine
• CAS: 1279016-04-4
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: JTNFORCLHHSZFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  40.22
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(5-phenyl-thieno[2,3-d]pyrimidine-4-yl)-piperidin-4-ylamine 、 2,2-dimethyl-6-(oxiran-2-ylmethoxy)-4H-benzo[d][1,3]dioxine 在 lithium perchlorate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以60%的产率得到1-((2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)oxy)-3-((1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-yl)amino)propan-2-ol
  参考文献：
  名称：

  Thienopyrimidines as β3-adrenoceptor agonists: Hit-to-lead optimization

  摘要：

  Resulting from a vHTS based on a pharmacophore alignment on known beta 3-adrenoceptor ligands, an aryloxypropanolamine scaffold comprising a thienopyrimidine moiety was further optimized as a human beta 3-AR agonist, yielding a lead compound with an excellent cellular activity of EC(50) = 20 pM, selectivity over h beta 1- and h beta 2- adrenoceptors and a promising safety profile. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.039
• 作为产物：
  描述：

  2,2-dimethyl-6-hydroxy-1,3-benzodioxane 、 环氧溴丙烷 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 48.0h， 以81%的产率得到2,2-dimethyl-6-(oxiran-2-ylmethoxy)-4H-benzo[d][1,3]dioxine
  参考文献：
  名称：

  Thienopyrimidines as β3-adrenoceptor agonists: Hit-to-lead optimization

  摘要：

  Resulting from a vHTS based on a pharmacophore alignment on known beta 3-adrenoceptor ligands, an aryloxypropanolamine scaffold comprising a thienopyrimidine moiety was further optimized as a human beta 3-AR agonist, yielding a lead compound with an excellent cellular activity of EC(50) = 20 pM, selectivity over h beta 1- and h beta 2- adrenoceptors and a promising safety profile. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.039