N-(2-methylphenyl)-3-bromo-2,2-difluoropropanoic acid amide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-methylphenyl)-3-bromo-2,2-difluoropropanoic acid amide
• 英文别名: 3-bromo-2,2-difluoro-N-(2-methylphenyl)propanamide
• 化学式: C₁₀H₁₀BrF₂NO
• 分子量: 278.096
• InChiKey: JGWIHHRPRWFVTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-methylphenyl)-3-bromo-2,2-difluoropropanoic acid amide 在 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以78%的产率得到N-(2-methylphenyl)-3,3-difluoroazetidin-2-one
  参考文献：
  名称：

  Inhibition of human leukocyte elastase by functionalized N-aryl azetidin-2-ones: substituent effects at C-3 and benzylic positions

  摘要：

  A series of functionalized N-aryl azetidin-2-ones with a latent alkylating group was prepared by a flexible four-step synthesis. They met criteria expected for a suicide-type inactivation of human leukocyte elastase (HLE) and porcine pancreatic elastase (PPE), with no inactivation of trypsin- and chymotrypsin-like proteases. The inhibition potency was dependent on the halogen substituents at C-3 (F, F; Cl, Cl; Br, Br) and the nature and the position relative to nitrogen of the latent benzylic leaving group (F, Cl, Br). Better inactivations of HLE compared with PPE were observed with azetidinones gem-disubstituted by Cl and Br rather than by F. Their protio analogs, which are devoid of the latent quinoniminium methide electrophile, behave as simple substrates of elastases.

  DOI：

  10.1016/0223-5234(96)88226-2
• 作为产物：
  描述：

  3-bromo-2,2-difluoropropanoyl chloride 、 邻甲苯胺 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以63%的产率得到N-(2-methylphenyl)-3-bromo-2,2-difluoropropanoic acid amide
  参考文献：
  名称：

  Inhibition of human leukocyte elastase by functionalized N-aryl azetidin-2-ones: substituent effects at C-3 and benzylic positions

  摘要：

  A series of functionalized N-aryl azetidin-2-ones with a latent alkylating group was prepared by a flexible four-step synthesis. They met criteria expected for a suicide-type inactivation of human leukocyte elastase (HLE) and porcine pancreatic elastase (PPE), with no inactivation of trypsin- and chymotrypsin-like proteases. The inhibition potency was dependent on the halogen substituents at C-3 (F, F; Cl, Cl; Br, Br) and the nature and the position relative to nitrogen of the latent benzylic leaving group (F, Cl, Br). Better inactivations of HLE compared with PPE were observed with azetidinones gem-disubstituted by Cl and Br rather than by F. Their protio analogs, which are devoid of the latent quinoniminium methide electrophile, behave as simple substrates of elastases.

  DOI：

  10.1016/0223-5234(96)88226-2