2,4,8-trimethyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl acetate | 1254180-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,4,8-trimethyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl acetate
• 英文别名: (2,4,8-trimethyl-6,7-dihydro-5H-1,8-naphthyridin-3-yl) acetate
• CAS: 1254180-92-1
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: SCBUTLMIULSJTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4,8-trimethyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl acetate 在 lithium aluminium tetrahydride 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以95%的产率得到2,4,8-trimethyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-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
• 作为产物：
  描述：

  乙酸酐 、 6-bromo-1,5,7-trimethyl-1,2,3,4-tetrahydro[1,8]naphthyridine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium hydroxide 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.67h， 以55%的产率得到2,4,8-trimethyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl acetate
  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