benzhydryl (7S,6R)-7-(phenoxyacetamido)-1-carba-1-dethia-3-methyl-3-cephem-4-carboxylate | 123266-35-3

• 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: benzhydryl (7S,6R)-7-(phenoxyacetamido)-1-carba-1-dethia-3-methyl-3-cephem-4-carboxylate
• 英文别名: benzhydryl (6R,7S)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 123266-35-3
• 化学式: C₃₀H₂₈N₂O₅
• 分子量: 496.563
• InChiKey: YLEZCZHANDARJF-RSXGOPAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzhydryl (7S,6R)-7-(phenoxyacetamido)-1-carba-1-dethia-3-methyl-3-cephem-4-carboxylate 在 三乙基硅烷 、 三氟乙酸 作用下， 以48%的产率得到(7S,6R)-7-(phenoxyacetamido)-1-carba-1-dethia-3-methyl-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Comparative reactivity of 1-carba-1-dethiacephalosporins with cephalosporins

  摘要：

  Nine matched pairs of cephalosporins and their 1-carba-1-dethiacephalosporin analogues have been compared with regard to microbiological activity, beta-lactam carbonyl infrared absorption, and aqueous stability. In general the microbiological activity of the pairs of compounds were very similar across a broad range of bacteria. The infrared absorption bands for the beta-lactam carbonyls of the pairs indicated a general trend for the 1-carba-1-dethiacephalosporins to absorb at lower frequencies than the corresponding cephalosporins. All of the 1-carba-1-dethiacephalosporins did however present a striking stability enhancement over their cephalosporin counterparts at pH = 10 or 11 in water. This marked contrast of MIC similarity with the observed differences in chemical reactivity clearly demonstrates hydroxide ion catalyzed hydrolysis is not a good model for transpeptidase activity unless the compounds comprise a limited domain of structural type.

  DOI：

  10.1021/jm00168a019
• 作为产物：
  描述：

  p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate 在 盐酸 、 双(乙腈)氯化钯(II) 、 lithium chloride 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 benzhydryl (7S,6R)-7-(phenoxyacetamido)-1-carba-1-dethia-3-methyl-3-cephem-4-carboxylate
  参考文献：
  名称：

  Comparative reactivity of 1-carba-1-dethiacephalosporins with cephalosporins

  摘要：

  Nine matched pairs of cephalosporins and their 1-carba-1-dethiacephalosporin analogues have been compared with regard to microbiological activity, beta-lactam carbonyl infrared absorption, and aqueous stability. In general the microbiological activity of the pairs of compounds were very similar across a broad range of bacteria. The infrared absorption bands for the beta-lactam carbonyls of the pairs indicated a general trend for the 1-carba-1-dethiacephalosporins to absorb at lower frequencies than the corresponding cephalosporins. All of the 1-carba-1-dethiacephalosporins did however present a striking stability enhancement over their cephalosporin counterparts at pH = 10 or 11 in water. This marked contrast of MIC similarity with the observed differences in chemical reactivity clearly demonstrates hydroxide ion catalyzed hydrolysis is not a good model for transpeptidase activity unless the compounds comprise a limited domain of structural type.

  DOI：

  10.1021/jm00168a019

文献信息

• Palladium-catalyzed chemistry of .beta.-lactam vinyl triflates: coupling with organostannanes and alkoxycarbonylation
  作者：Gwendolyn K. Cook、William J. Hornback、Chris L. Jordan、John H. McDonald、John E. Munroe

  DOI：10.1021/jo00285a037

  日期：1989.11