2,3-dibromo-2-fluoropropanoyl chloride | 111773-26-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 2,3-dibromo-2-fluoropropanoyl chloride
• CAS: 111773-26-3
• 化学式: C₃H₂Br₂ClFO
• 分子量: 268.308
• InChiKey: CYCDFESJIDQDGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  8.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,3-dibromo-2-fluoropropanoyl chloride 、 邻甲苯胺 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以98%的产率得到N-(2-methylphenyl)-2,3-dibromo-2-fluoropropanoic 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

文献信息

• N-Aryl 3-halogenated azetidin-2-ones and benzocarbacephems, inhibitors of .beta.-lactamases
  作者：Roger Joyeau、Huguette Molines、Roger Labia、Michel Wakselman

  DOI：10.1021/jm00397a018

  日期：1988.2

  N-(3-Carboxy-6-methylphenyl)-3-fluoroazetidin-2-one and a series of related N-aryl-3-halo- and -3,3-dihaloazetidinones 3, in which the halo substituent is a fluorine or a bromine atom, were prepared by using the Wasserman procedure of cyclization of beta-bromopropionamides as a key step. Their affinities for the TEM-1 beta-lactamase were determined and compared with those of a series of tricyclic azetidinones

  N-（3-羧基-6-甲基苯基）-3-氟氮杂环丁烷-2-酮和一系列相关的N-芳基-3-卤代和-3,3-二卤代氮杂环丁酮3，其中卤素取代基是氟或β-溴丙酰胺环化的Wasserman程序制备了一个溴原子作为关键步骤。确定了它们对TEM-1β-内酰胺酶的亲和力，并将其与一系列三环氮杂环丁酮，苯并甲酰胺2和已知的β-内酰胺酶抑制剂的亲和力进行了比较。β-内酰胺2和3充当竞争性抑制剂，而不是酶的底物；卤素取代（系列3）和环菌株（系列2）都不会诱导酶水解。