2,3-dihydroxy-3-phenyl-1,2,3,4-tetrahydro-1,6-naphthyridine-5-carboxaldehyde | 147440-94-6

• 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: 2,3-dihydroxy-3-phenyl-1,2,3,4-tetrahydro-1,6-naphthyridine-5-carboxaldehyde
• 英文别名: 2,3-dihydroxy-3-phenyl-2,4-dihydro-1H-1,6-naphthyridine-5-carbaldehyde
• CAS: 147440-94-6
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: ZSTBILBFNDGTAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-dihydroxy-3-phenyl-1,2,3,4-tetrahydro-1,6-naphthyridine-5-carboxaldehyde 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以30%的产率得到3-phenyl-1,6-naphthyridine-5-carboxaldehyde
  参考文献：
  名称：

  Regioselective Metalation of Ortho-Aminopicolines Using the Pivaloyl Group as a Directing Group: Synthesis of Naphthyridines

  摘要：

  2-(1,3-Dioxan-2-yl)-3-methyl-4- and 2-chloro-3,4-dimethyl-5-pivaloylaminopyridines were prepared and converted to 1,6- and 1,7-naphthyridines via regioselective lithiation of the ortho-methyl group, reaction with 2,2-diethoxyacetophenone and subsequent acid-catalyzed cyclization.

  DOI：

  10.1080/00397919308009790
• 作为产物：
  描述：

  N-<3-(3,3-diethoxy-2-hydroxy-2-phenyl-propyl)-2-<1,3>-dioxan-2-yl-pyridin-4-yl>-2,2-dimethyl-propanamide 在 硫酸 作用下， 以65%的产率得到2,3-dihydroxy-3-phenyl-1,2,3,4-tetrahydro-1,6-naphthyridine-5-carboxaldehyde
  参考文献：
  名称：

  Regioselective Metalation of Ortho-Aminopicolines Using the Pivaloyl Group as a Directing Group: Synthesis of Naphthyridines

  摘要：

  2-(1,3-Dioxan-2-yl)-3-methyl-4- and 2-chloro-3,4-dimethyl-5-pivaloylaminopyridines were prepared and converted to 1,6- and 1,7-naphthyridines via regioselective lithiation of the ortho-methyl group, reaction with 2,2-diethoxyacetophenone and subsequent acid-catalyzed cyclization.

  DOI：

  10.1080/00397919308009790

文献信息

• Regioselective Metalation of Ortho-Aminopicolines Using the Pivaloyl Group as a Directing Group: Synthesis of Naphthyridines
  作者：Alexander Straub

  DOI：10.1080/00397919308009790

  日期：1993.2

  2-(1,3-Dioxan-2-yl)-3-methyl-4- and 2-chloro-3,4-dimethyl-5-pivaloylaminopyridines were prepared and converted to 1,6- and 1,7-naphthyridines via regioselective lithiation of the ortho-methyl group, reaction with 2,2-diethoxyacetophenone and subsequent acid-catalyzed cyclization.