1-(5-methoxyquinolin-8-yl)-4-phenylazetidin-2-one | 1514927-38-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-(5-methoxyquinolin-8-yl)-4-phenylazetidin-2-one
• CAS: 1514927-38-8
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: DQFJPTAKLYACIU-UHFFFAOYSA-N

物化性质

• 沸点：
  592.5±50.0 °C(predicted)
• 密度：
  1.277±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  42.43
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(5-methoxyquinolin-8-yl)-4-phenylazetidin-2-one 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以70%的产率得到4-苯基-2-氮杂环丁酮
  参考文献：
  名称：

  Palladium-Catalyzed Unactivated C(sp³)–H Bond Activation and Intramolecular Amination of Carboxamides: A New Approach to β-Lactams

  摘要：

  An efficient method to synthesize the beta-lactams with high regioselectivity via Pd-catalyzed C(sp(3))-H bond activation and intramolecular arnination of simple and readily available aminoquinoline carboxamides was demonstrated. C6F5I plays a significant role in the formation of the C-N bond of the four-membered ring beta-lactams. High yield along with wide substrate scope and functional group tolerance makes this reaction applicable to build natural-product-derived beta-lactams. This method has been applied to the efficient synthesis of the beta-lactamase inhibitor MK-8712.

  DOI：

  10.1021/ol403364k
• 作为产物：
  描述：

  N-(5-methoxyquinolin-8-yl)-3-phenylpropanamide 在 2,3,4,5,6-五氟碘苯 、 silver(I) acetate 、 palladium diacetate 作用下， 以73%的产率得到1-(5-methoxyquinolin-8-yl)-4-phenylazetidin-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Unactivated C(sp³)–H Bond Activation and Intramolecular Amination of Carboxamides: A New Approach to β-Lactams

  摘要：

  An efficient method to synthesize the beta-lactams with high regioselectivity via Pd-catalyzed C(sp(3))-H bond activation and intramolecular arnination of simple and readily available aminoquinoline carboxamides was demonstrated. C6F5I plays a significant role in the formation of the C-N bond of the four-membered ring beta-lactams. High yield along with wide substrate scope and functional group tolerance makes this reaction applicable to build natural-product-derived beta-lactams. This method has been applied to the efficient synthesis of the beta-lactamase inhibitor MK-8712.

  DOI：

  10.1021/ol403364k