1,4,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-5-ol | 1254180-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1,4,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-5-ol
• 英文别名: 1,4,6-Trimethylpyrrolo[2,3-b]pyridin-5-ol；1,4,6-trimethylpyrrolo[2,3-b]pyridin-5-ol
• CAS: 1254180-90-9
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: HSZCTFCJCFVNDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,4,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl acetate 在 甲醇 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 以97%的产率得到1,4,6-trimethyl-1H-pyrrolo[2,3-b]pyridin-5-ol
  参考文献：
  名称：

  Concise Synthesis of Bicyclic Pyridinol Antioxidants

  摘要：

  The recently reported bicyclic pyridinols 1 and 2 are highly effective antioxidants exhibiting 88- and 28-fold greater potency, respectively, than a-tocopherol when assayed for their ability to suppress the autoxidation of methyl linoleate. Described herein is a short, economical, and scalable strategy for the synthesis of this novel group of antioxidants, as well as analogues 3-6. Key reactions involved the cyclocondensation reaction of lactam acetals with enaminone 7 and selective functionalizaton of the heterocyclic systems.

  DOI：

  10.1021/ol102217c

文献信息

• Concise Synthesis of Bicyclic Pyridinol Antioxidants
  作者：Jun Lu、Xiaoqing Cai、Sidney M. Hecht

  DOI：10.1021/ol102217c

  日期：2010.11.19

  The recently reported bicyclic pyridinols 1 and 2 are highly effective antioxidants exhibiting 88- and 28-fold greater potency, respectively, than a-tocopherol when assayed for their ability to suppress the autoxidation of methyl linoleate. Described herein is a short, economical, and scalable strategy for the synthesis of this novel group of antioxidants, as well as analogues 3-6. Key reactions involved the cyclocondensation reaction of lactam acetals with enaminone 7 and selective functionalizaton of the heterocyclic systems.