6β-(2,2-dimethyl-5-oxo-4-phenyl-2,5-dihydro-imidazol-1-yl)-1α-oxo-1λ⁴-penicillanic acid | 65185-50-4

• 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: 6β-(2,2-dimethyl-5-oxo-4-phenyl-2,5-dihydro-imidazol-1-yl)-1α-oxo-1λ⁴-penicillanic acid
• 英文别名: (2S,4R,5R,6R)-6-(2,2-dimethyl-5-oxo-4-phenylimidazol-1-yl)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid；(2S,4R,5R,6R)-6-(2,2-dimethyl-5-oxo-4-phenylimidazol-1-yl)-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 65185-50-4
• 化学式: C₁₉H₂₁N₃O₅S
• 分子量: 403.459
• InChiKey: YXPQOARZHNIVPL-ZKFINDEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  hetacillin potassium 在 臭氧 作用下， 以 水 、 丙酮 为溶剂， 生成 6β-(2,2-dimethyl-5-oxo-4-phenyl-2,5-dihydro-imidazol-1-yl)-1α-oxo-1λ⁴-penicillanic acid
  参考文献：
  名称：

  Hetacillin (R)- and (S)-sulfoxides. Synthesis and structure-activity relationships

  摘要：

  Hetacillin was oxidized with m-chloroperbenzoic acid to give the corresponding (R)- and (S)-sulfoxides. Ozonization of hetacillin not only oxidized the sulfide but caused unexpected oxidation of the imidazolidine ring to a 2H-imidazoline. The biological spectrum showed the (R)-sulfoxide to be appreciably more active than the (S)-sulfoxide.

  DOI：

  10.1021/jm00200a022

文献信息

• Hetacillin (R)- and (S)-sulfoxides. Synthesis and structure-activity relationships
  作者：W. J. Gottstein、C. U. Kim、K. M. Shih、D. N. McGregor

  DOI：10.1021/jm00200a022

  日期：1978.2

  Hetacillin was oxidized with m-chloroperbenzoic acid to give the corresponding (R)- and (S)-sulfoxides. Ozonization of hetacillin not only oxidized the sulfide but caused unexpected oxidation of the imidazolidine ring to a 2H-imidazoline. The biological spectrum showed the (R)-sulfoxide to be appreciably more active than the (S)-sulfoxide.