dimethyl 2,6-diisopropyl-4-hydroxy-3,5-pyridine-dicarboxylate | 470717-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: dimethyl 2,6-diisopropyl-4-hydroxy-3,5-pyridine-dicarboxylate
• 英文别名: diMethyl 2,6-diisopropyl-4-hydroxy-3,5-pyridine-dicarboxylate；dimethyl 4-oxo-2,6-di(propan-2-yl)-1H-pyridine-3,5-dicarboxylate
• CAS: 470717-49-8
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: LOXLDVUKEKOTFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2,6-diisopropyl-4-hydroxy-3,5-pyridine-dicarboxylate 在 lithium aluminium tetrahydride 、 potassium carbonate 、 红铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 0.5h， 生成 1-[4-(2-Benzyloxy-4-fluoro-phenyl)-2,6-diisopropyl-5-vinyl-pyridin-3-yl]-ethanol
  参考文献：
  名称：

  Integration of optimized substituent patterns to produce highly potent 4-aryl-pyridine glucagon receptor antagonists

  摘要：

  Optimized substituent patterns in 4-arul-puridine glucagon receptor antagonists were merged to produce highly potent derivatives containing both a 3-[(1R)-hydroxyethyl] and a 2'-hydroxy group. Due to restricted rotation of the phenyl-pyridine bond, these analogues exist as four isomers. A diastereoselective methylcopper reaction as developed to facilitate the synthesis, and single isomers ere isolated with activities in the range IC50 = 10 25 nM. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00736-9
• 作为产物：
  描述：

  dimethyl 2,6-diisopropyl-4-oxo-2H-pyran-3,5-dicarboxylate 在 氨 作用下， 以 甲醇 为溶剂， 以92%的产率得到dimethyl 2,6-diisopropyl-4-hydroxy-3,5-pyridine-dicarboxylate
  参考文献：
  名称：

  Optimization of the 4-aryl group of 4-aryl-pyridine glucagon antagonists: development of an efficient, alternative synthesis

  摘要：

  A narrow structure-activity relationship was established for the 4-aryl group in 4-aryl-pyridine glucagon antagonists, with only small substituents being well-tolerated, and only at the 3'- and 4'-positions. However, substitution with a 2'-hydroxy group gave a ca. 3-fold increase in activity (e.g., 4'-fluoro-2'-hydroxy analogue 33, IC50 = 190 nM). For efficient preparation of 2'-substituted phenylpyridines, a novel synthesis via pyrones and 4-methoxy-pyridines was developed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00143-9