prop-2-enyl 2-[(2R,3S)-2-benzoylsulfanyl-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-1-yl]-2-oxoacetate | 164728-34-1

• 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: prop-2-enyl 2-[(2R,3S)-2-benzoylsulfanyl-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-1-yl]-2-oxoacetate
• CAS: 164728-34-1
• 化学式: C₂₃H₃₁NO₆SSi
• 分子量: 477.654
• InChiKey: FHSWBLHWYDRYQM-OXFYSEKESA-N

物化性质

• 沸点：
  519.9±60.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  89.98
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  prop-2-enyl 2-[(2R,3S)-2-benzoylsulfanyl-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-1-yl]-2-oxoacetate 在 亚磷酸三乙酯 作用下， 以 xylene 为溶剂， 反应 11.0h， 生成 prop-2-enyl (5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-7-oxo-3-phenyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Structure-activity relationships of penem antibiotics: Crystallographic structures and implications for their antimicrobial activities

  摘要：

  Twelve closely related crystal structures of the penem derivatives revealed a characteristic short contact of the oxygen atom in the C2 side-chains with the S1 atom. The side-chain conformations of the crystal structures showed a good correlation with the antimicrobial activity. In particular, the penems which show high antimicrobial activity have similar torsion angles for S1-C2-C1'-C2', suggesting that the disposition of the C2' atom would be important for binding to penicillin-interacting enzymes. Two conformations of the C6 hydroxyethyl group were observed in the crystal structures. Of those two, the conformation with a larger torsion angle (delta = 179.2 degrees) is deduced to be the enzyme-bound conformation in the Michaelis complex. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00073-4
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 在 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.17h， 生成 prop-2-enyl 2-[(2R,3S)-2-benzoylsulfanyl-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-1-yl]-2-oxoacetate
  参考文献：
  名称：

  Structure-activity relationships of penem antibiotics: Crystallographic structures and implications for their antimicrobial activities

  摘要：

  Twelve closely related crystal structures of the penem derivatives revealed a characteristic short contact of the oxygen atom in the C2 side-chains with the S1 atom. The side-chain conformations of the crystal structures showed a good correlation with the antimicrobial activity. In particular, the penems which show high antimicrobial activity have similar torsion angles for S1-C2-C1'-C2', suggesting that the disposition of the C2' atom would be important for binding to penicillin-interacting enzymes. Two conformations of the C6 hydroxyethyl group were observed in the crystal structures. Of those two, the conformation with a larger torsion angle (delta = 179.2 degrees) is deduced to be the enzyme-bound conformation in the Michaelis complex. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00073-4