(6R,7R)-7-tert-Butoxycarbonylamino-3-((E)-2-methanesulfonyl-vinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester | 180525-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6R,7R)-7-tert-Butoxycarbonylamino-3-((E)-2-methanesulfonyl-vinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS: 180525-07-9
• 化学式: C₂₈H₃₀N₂O₇S₂
• 分子量: 570.687
• InChiKey: SHSNIARUHVFKBU-GEFSTLMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  119.08
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (6R,7R)-7-tert-Butoxycarbonylamino-3-((E)-2-methanesulfonyl-vinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 对甲苯磺酸 、 sodium hydrogensulfite 、 苯甲醚 作用下， 以 四氢呋喃 、 水 、 乙腈 、 三氟乙酸 为溶剂， 反应 0.08h， 生成 (6R,7R)-3-((E)-2-Methanesulfonyl-vinyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of cephems bearing olefinic sulfoxide side chains as potential β-lactamase inhibitors

  摘要：

  Several cephems bearing vinyl sulfoxide and sulfone moieties at C-3 were prepared by the Stille coupling of a 3-trifloxy cephem with stannanes. The sulfoxides were designed to be suicide lactamase inhibitors. None of the cephems described in this study functioned as an enzyme inhibitor, but two derivatives displayed interesting biological activity against Methycillin - resistant S. Aureus. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00285-5
• 作为产物：
  描述：

  (6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 、 Tributyl-((E)-2-methanesulfonyl-vinyl)-stannane 在 N-甲基吡咯烷酮 、 tris-(dibenzylideneacetone)dipalladium(0) 、 zinc(II) chloride 作用下， 反应 48.0h， 以85%的产率得到(6R,7R)-7-tert-Butoxycarbonylamino-3-((E)-2-methanesulfonyl-vinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  Synthesis of cephems bearing olefinic sulfoxide side chains as potential β-lactamase inhibitors

  摘要：

  Several cephems bearing vinyl sulfoxide and sulfone moieties at C-3 were prepared by the Stille coupling of a 3-trifloxy cephem with stannanes. The sulfoxides were designed to be suicide lactamase inhibitors. None of the cephems described in this study functioned as an enzyme inhibitor, but two derivatives displayed interesting biological activity against Methycillin - resistant S. Aureus. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00285-5