(6R,7R)-3-Acetoxymethyl-7-[(R)-2-tert-butoxycarbonylamino-2-(2,3-dihydro-benzofuran-5-yl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 71922-87-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6R,7R)-3-Acetoxymethyl-7-[(R)-2-tert-butoxycarbonylamino-2-(2,3-dihydro-benzofuran-5-yl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 71922-87-7
• 化学式: C₂₅H₂₉N₃O₉S
• 分子量: 547.586
• InChiKey: NBEWIOFLQMMLIV-JBYIUTFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  160.57
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (6R,7R)-3-Acetoxymethyl-7-[(R)-2-tert-butoxycarbonylamino-2-(2,3-dihydro-benzofuran-5-yl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 盐酸 作用下， 以 硝基甲烷 为溶剂， 生成 (6R,7R)-3-Acetoxymethyl-7-[(R)-2-amino-2-(2,3-dihydro-benzofuran-5-yl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Orally active cephalosporins and penicillins

  摘要：

  A number of orally active cephalosporins and penicillins with interesting biological activity were synthesized. Two of these, 7-[[[3,4-(methylenedioxy)phenyl]glycyl]amino]deacetoxycephalosporanic acid and 7-[[2-(2,3-dihydro-5-benzofuranyl)glycyl]amino]deacetoxycephalosporanic acid were considerably more active than cephalexin both in vitro and in vivo against staphylococcal and streptococcal infections.

  DOI：

  10.1021/jm00178a011
• 作为产物：
  描述：

  (R)-2-(2,3-dihydro-5-benzofuranyl)glycine 在 氯甲酸乙酯 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 34.0h， 生成 (6R,7R)-3-Acetoxymethyl-7-[(R)-2-tert-butoxycarbonylamino-2-(2,3-dihydro-benzofuran-5-yl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Orally active cephalosporins and penicillins

  摘要：

  A number of orally active cephalosporins and penicillins with interesting biological activity were synthesized. Two of these, 7-[[[3,4-(methylenedioxy)phenyl]glycyl]amino]deacetoxycephalosporanic acid and 7-[[2-(2,3-dihydro-5-benzofuranyl)glycyl]amino]deacetoxycephalosporanic acid were considerably more active than cephalexin both in vitro and in vivo against staphylococcal and streptococcal infections.

  DOI：

  10.1021/jm00178a011