(3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]hept-2E-ylidene)acetaldehyde | 854139-78-9

• 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: (3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]hept-2E-ylidene)acetaldehyde
• 英文别名: (2E)-2-[(5R)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptan-2-ylidene]acetaldehyde；(2E)-2-[(5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptan-2-ylidene]acetaldehyde
• CAS: 854139-78-9
• 化学式: C₉H₁₁NO₄S
• 分子量: 229.257
• InChiKey: JSZRUSAIHIBEAN-GWSCVKMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]hept-2E-ylidene)acetaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 氨基磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.75h， 以68%的产率得到(3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]hept-2E-ylidene)acetic acid
  参考文献：
  名称：

  Synthesis and Evaluation of 3-(Carboxymethylidene)- and 3-(Carboxymethyl)penicillinates as Inhibitors of β-Lactamase

  摘要：

  Penicillin-resistant bacteria can often be treated through the co-administration of an antibiotic and a-lactamase inhibitor. Current inhibitors target only class A beta-lactamases. We report two new series of C3-modified penicillin sulfones, having either a simple methylene group (i.e., a homologue) or exocyclic unsaturation between the thiazolidine ring and the C3 carboxylate. The homologue has 10-fold better activity against a class C beta-lactamase than does sulbactam itself. By contrast, the exocyclic C3 unsaturated compounds are less active.

  DOI：

  10.1021/jo050004s
• 作为产物：
  描述：

  舒巴坦酸 在 dimethyl sulfide borane 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 32.34h， 生成 (3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]hept-2E-ylidene)acetaldehyde
  参考文献：
  名称：

  Synthesis and Evaluation of 3-(Carboxymethylidene)- and 3-(Carboxymethyl)penicillinates as Inhibitors of β-Lactamase

  摘要：

  Penicillin-resistant bacteria can often be treated through the co-administration of an antibiotic and a-lactamase inhibitor. Current inhibitors target only class A beta-lactamases. We report two new series of C3-modified penicillin sulfones, having either a simple methylene group (i.e., a homologue) or exocyclic unsaturation between the thiazolidine ring and the C3 carboxylate. The homologue has 10-fold better activity against a class C beta-lactamase than does sulbactam itself. By contrast, the exocyclic C3 unsaturated compounds are less active.

  DOI：

  10.1021/jo050004s

文献信息

• Synthesis and Evaluation of 3-(Carboxymethylidene)- and 3-(Carboxymethyl)penicillinates as Inhibitors of β-Lactamase
  作者：John D. Buynak、Venkat Rao Ghadachanda、Lakshminaryana Vogeti、Hongming Zhang、Hansong Chen

  DOI：10.1021/jo050004s

  日期：2005.5.1

  Penicillin-resistant bacteria can often be treated through the co-administration of an antibiotic and a-lactamase inhibitor. Current inhibitors target only class A beta-lactamases. We report two new series of C3-modified penicillin sulfones, having either a simple methylene group (i.e., a homologue) or exocyclic unsaturation between the thiazolidine ring and the C3 carboxylate. The homologue has 10-fold better activity against a class C beta-lactamase than does sulbactam itself. By contrast, the exocyclic C3 unsaturated compounds are less active.