7-pivaloylamino-2-chloro-1,8-naphthyridine | 874894-09-4

• 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: 7-pivaloylamino-2-chloro-1,8-naphthyridine
• 英文别名: N-(7-chloro-1,8-naphthyridin-2-yl)-2,2-dimethylpropanamide
• CAS: 874894-09-4
• 化学式: C₁₃H₁₄ClN₃O
• 分子量: 263.727
• InChiKey: WYOMEEGPHCHEMM-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  469.7±40.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-pivaloylamino-2-chloro-1,8-naphthyridine 、 2-乙基己酰胺 在 palladium diacetate 、 potassium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以54%的产率得到7-(pivaloylamino)-2-(2-ethylhexanoylamino)-1,8-naphthyridine
  参考文献：
  名称：

  Pd-Catalyzed Amidation of 2-Chloro- and 2,7-Dichloro-1,8-naphthyridines

  摘要：

  The catalytic amidation between 2-chloro- and 2,7-dichloro-1,8-naphthyridines and primary amides bearing functional groups is reported. When Pd(OAc)(2), xantphos, and K2CO3 are used, it is possible to obtain symmetric as well as non-symmetric 2,7-diamido-1,8-naphthyridines in 50-90% yield with good functional-group tolerance. Monoamidation of 2,7-dichloro-1,8-naphthyridine using 0.9 equiv of the amide proceeded with good selectivity compared to the formation of the diamide, but as a result of the difficult isolation of the product, isolated yields were poor to moderate (22-42%).

  DOI：

  10.1021/jo051864b
• 作为产物：
  描述：

  2,2-dimethy-N-(7-oxo-7,8-dihydro-1,8-napthyridin-2-yl)-propionamide 在 三氯氧磷 作用下， 反应 4.0h， 以80%的产率得到7-pivaloylamino-2-chloro-1,8-naphthyridine
  参考文献：
  名称：

  Pd-Catalyzed Amidation of 2-Chloro- and 2,7-Dichloro-1,8-naphthyridines

  摘要：

  The catalytic amidation between 2-chloro- and 2,7-dichloro-1,8-naphthyridines and primary amides bearing functional groups is reported. When Pd(OAc)(2), xantphos, and K2CO3 are used, it is possible to obtain symmetric as well as non-symmetric 2,7-diamido-1,8-naphthyridines in 50-90% yield with good functional-group tolerance. Monoamidation of 2,7-dichloro-1,8-naphthyridine using 0.9 equiv of the amide proceeded with good selectivity compared to the formation of the diamide, but as a result of the difficult isolation of the product, isolated yields were poor to moderate (22-42%).

  DOI：

  10.1021/jo051864b