potassium (6R,7R)-3-methyl-8-oxo-7-(2-phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 10209-12-8

• 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: potassium (6R,7R)-3-methyl-8-oxo-7-(2-phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 英文别名: potassium;(6R,7R)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 10209-12-8
• 化学式: C₁₆H₁₅N₂O₅S*K
• 分子量: 386.47
• InChiKey: VGYNQROPVZAMNB-XRZFDKQNSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.51
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  potassium (6R,7R)-3-methyl-8-oxo-7-(2-phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 、 1-碘代丙烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以69%的产率得到(6R,7R)-propyl 3-methyl-8-oxo-7-(2-phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Design and synthesis of new cephalosporin antibiotics

  摘要：

  Cephalosporins are important antibiotics. We synthesized new cephalosporin analogs containing novel side chains of methyl, propyl, benzyl, and phenoxy groups. Four synthetic methods with N-alkylation and N-acylation at position C-7 and esterification at position C-4 of 7-aminodesacetoxycephalosporanic acid are reported here.

  DOI：

  10.1007/s00706-014-1152-6
• 作为产物：
  描述：

  (6R,7R)-3-Methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 potassium 2-ethylhexanoate 作用下， 以 正丁醇 为溶剂， 反应 0.08h， 以0.2 g的产率得到potassium (6R,7R)-3-methyl-8-oxo-7-(2-phenoxyacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Design and synthesis of new cephalosporin antibiotics

  摘要：

  Cephalosporins are important antibiotics. We synthesized new cephalosporin analogs containing novel side chains of methyl, propyl, benzyl, and phenoxy groups. Four synthetic methods with N-alkylation and N-acylation at position C-7 and esterification at position C-4 of 7-aminodesacetoxycephalosporanic acid are reported here.

  DOI：

  10.1007/s00706-014-1152-6