(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 | 123054-32-0

• 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-8-oxo-3-trifluoromethanesulfonyloxy-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• 英文别名: benzhydryl (6R,7R)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-3-(trifluoromethylsulfonyloxy)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 123054-32-0
• 化学式: C₂₆H₂₅F₃N₂O₈S₂
• 分子量: 614.62
• InChiKey: VTFJNHBQOIGXMW-XMSQKQJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  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 在 N-甲基吡咯烷酮 、 tris-(dibenzylideneacetone)dipalladium(0) 、 对甲苯磺酸 、 sodium hydrogensulfite 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 48.0h， 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 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
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (6R,7R)-7-tert-Butoxycarbonylamino-3-hydroxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以69%的产率得到(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
  参考文献：
  名称：

  A general route to 3-functionalized 3-norcephalosporins

  摘要：

  DOI：

  10.1021/jo00281a048

文献信息

• Palladium catalysis in cephalosporin chemistry: general methodology for the synthesis of cephem side chains
  作者：Vittorio Farina、Stephen R. Baker、Daniel A. Benigni、Sheila I. Hauck、Chester Sapino

  DOI：10.1021/jo00310a014

  日期：1990.11
• Cu(I)-catalyzed substitution reactions of activated vinyl triflates with functionalized organozinc reagents
  作者：Bruce H. Lipshutz、Randall W. Vivian

  DOI：10.1016/s0040-4039(99)00355-x

  日期：1999.4

  Treatment of a mixed, functionalized dialkylzinc species with catalytic amounts of CuCN . 2LiCl produces a reagent which readily displaces an activated vinyl triflate in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of cephems bearing olefinic sulfoxide side chains as potential β-lactamase inhibitors
  作者：Vittorio Farina、Sheila I. Hauck、Raymond A. Firestone

  DOI：10.1016/s0960-894x(96)00285-5

  日期：1996.7

  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
• A general route to 3-functionalized 3-norcephalosporins
  作者：Vittorio Farina、Stephen R. Baker、Sheila I. Hauck

  DOI：10.1021/jo00281a048

  日期：1989.9