rac-<2R,3S(R)>-2-(3-bromo-2-oxopropyl)-3-(1-hydroxyethyl)-4-oxo-α-(triphenylphosphoranylidene)azetidine-1-acetic acid (2,2-dimethyl-1-oxopropoxy)methyl ester | 138423-45-7

• 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: rac-<2R,3S(R)>-2-(3-bromo-2-oxopropyl)-3-(1-hydroxyethyl)-4-oxo-α-(triphenylphosphoranylidene)azetidine-1-acetic acid (2,2-dimethyl-1-oxopropoxy)methyl ester
• 英文别名: [2-[(2R,3S)-2-(3-bromo-2-oxopropyl)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidin-1-yl]-2-(triphenyl-λ5-phosphanylidene)acetyl]oxymethyl 2,2-dimethylpropanoate
• CAS: 138423-45-7
• 化学式: C₃₄H₃₇BrNO₇P
• 分子量: 682.548
• InChiKey: IVPNRXWSBRHXDN-HCLMJZEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rac-<2R,3S(R)>-2-(3-bromo-2-oxopropyl)-3-(1-hydroxyethyl)-4-oxo-α-(triphenylphosphoranylidene)azetidine-1-acetic acid (2,2-dimethyl-1-oxopropoxy)methyl ester 在 吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 rac-<2R,3S(R)>-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid <<3-<1-<(trimethylsilyl)oxy>ethyl>-1-<2-<(2,2-dimethyl-1-oxopropoxy)methoxy>-2-oxo-1-(triphenylphosphoranylidene)etyl>-4-oxo-2-azeti.>>
  参考文献：
  名称：

  Dual-action penems and carbapenems

  摘要：

  Two new series of dual-action antibacterial agents were synthesized in which penems and carbapenems were linked at the 2'-position to quinolones through either an ester or a carbamate moiety. Potent, broad-spectrum antibacterial activity was observed for both classes of compounds, indicative of a dual-mode of action.

  DOI：

  10.1021/jm00088a019
• 作为产物：
  描述：

  rac-<2R,3S(R)>-2-(3-bromo-2,2-dimethoxypropyl)-3-(1-hydroxyethyl)-4-oxo-α-(triphenylphosphoranylidene)-1-azetidineacetic acid (2,2-dimethyl-1-oxopropyl)methyl ester 在 氢溴酸 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以52%的产率得到rac-<2R,3S(R)>-2-(3-bromo-2-oxopropyl)-3-(1-hydroxyethyl)-4-oxo-α-(triphenylphosphoranylidene)azetidine-1-acetic acid (2,2-dimethyl-1-oxopropoxy)methyl ester
  参考文献：
  名称：

  Dual-action penems and carbapenems

  摘要：

  Two new series of dual-action antibacterial agents were synthesized in which penems and carbapenems were linked at the 2'-position to quinolones through either an ester or a carbamate moiety. Potent, broad-spectrum antibacterial activity was observed for both classes of compounds, indicative of a dual-mode of action.

  DOI：

  10.1021/jm00088a019