p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-vinyl-1-carba-1-dethia-3-cephem-4-carboxylate | 127023-91-0

• 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: p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-vinyl-1-carba-1-dethia-3-cephem-4-carboxylate
• 英文别名: (4-nitrophenyl)methyl (6R,7S)-3-ethenyl-8-oxo-7-[(2-phenoxyacetyl)amino]-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 127023-91-0
• 化学式: C₂₅H₂₃N₃O₇
• 分子量: 477.474
• InChiKey: QUUBRDWMQJQHPI-IRLDBZIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  128.08
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-vinyl-1-carba-1-dethia-3-cephem-4-carboxylate 在 N-甲基吗啉 、 吡啶 、 臭氧 、 溶剂黄146 、 lithium tri-t-butoxyaluminum hydride 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.67h， 生成 (7S,6R)-7-<<(2-amino-4-thiazolyl)methoximinoacetyl>amino>-3-<(1-pyridiniumyl)methyl>-1-carba-1-dethia-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
• 作为产物：
  描述：

  三丁基乙烯基锡 、 p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate 在 双(乙腈)氯化钯(II) 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以77%的产率得到p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-vinyl-1-carba-1-dethia-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

• Snyder, Nancy J.; Paschal, Jonathan W.; Elzey, Thomas K., Heterocycles, 1991, vol. 32, # 11, p. 2193 - 2204
  作者：Snyder, Nancy J.、Paschal, Jonathan W.、Elzey, Thomas K.、Spry, Douglas O.

  DOI：——

  日期：——
• SPRY, DOUGLAS O.;SNYDER, NANCY J.;KASHER, JEFFREY S., J. ANTIBIOTICS, 42,(1989) N1, C. 1653-1660
  作者：SPRY, DOUGLAS O.、SNYDER, NANCY J.、KASHER, JEFFREY S.

  DOI：——

  日期：——