p-methoxybenzyl(1S,6R,7R)-1-oxo-7-phenylacetamido-3-(trifluoro-methanesulphonyloxy)ceph-3-em-4-carboxylate | 154256-01-6

• 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-methoxybenzyl(1S,6R,7R)-1-oxo-7-phenylacetamido-3-(trifluoro-methanesulphonyloxy)ceph-3-em-4-carboxylate
• 英文别名: p-methoxybenzyl (1S,6R,7R)-1-oxo-7-phenylacetamido-3-trifluoromethanesulphonyloxyceph-3-em-4-carboxylate；(4-methoxyphenyl)methyl (5S,6R,7R)-5,8-dioxo-7-[(2-phenylacetyl)amino]-3-(trifluoromethylsulfonyloxy)-5λ4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 154256-01-6
• 化学式: C₂₄H₂₁F₃N₂O₉S₂
• 分子量: 602.566
• InChiKey: GXQMNDJXQYKXCE-YKJITRBQSA-N

物化性质

• 沸点：
  847.2±65.0 °C(predicted)
• 密度：
  1.63±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  p-methoxybenzyl(1S,6R,7R)-1-oxo-7-phenylacetamido-3-(trifluoro-methanesulphonyloxy)ceph-3-em-4-carboxylate 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以71%的产率得到p-Methoxybenzyl (6R,7R)-1,1-dioxo-7-phenylacetamido-3-(trifluoromethanesulphonyloxy)ceph-3-em-4-carboxylate
  参考文献：
  名称：

  Cephalosporin derivatives

  摘要：

  式(I)的化合物或其盐：其中R.sup.1是氢，甲氧基或甲酰胺基；R.sup.2是酰基；CO.sub.2 R.sup.3是羧基或羧酸根离子，或R.sup.3是易于去除的羧基保护基或药用盐形成基或体内可水解的酯基；R.sup.4、R.sup.5、R.sup.6和R.sup.7独立地代表氢或键或取代基，或可形成环状系统。这些化合物具有抗菌活性。

  公开号：

  US05578592A1
• 作为产物：
  描述：

  (7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到p-methoxybenzyl(1S,6R,7R)-1-oxo-7-phenylacetamido-3-(trifluoro-methanesulphonyloxy)ceph-3-em-4-carboxylate
  参考文献：
  名称：

  Cycloadditions of Cephalosporins. A Comprehensive Study of the Reaction of Cephalosporin Triflates with Olefins, Acetylenes, and Dienes To Form [2 + 2] and [4 + 2] Adducts

  摘要：

  Novel polycyclic cephalosporins are formed by the reaction of cephalosporin triflates with various unsaturated compounds in the presence of Hunigs base. 2,3-Fused cyclobutane and cyclobutene cephems are obtained with olefins and acetylenes, respectively, whereas [4 + 2] cycloadducts are obtained with furan. The reaction has been rationalized by invoking the intermediacy of a strained 6-membered cyclic allene. The allene undergoes an orbital symmetry allowed concerted (pi)2(8), + (pi)2(a), cycloaddition with olefins and acetylenes and a (pi)4(s) + (pi)2(s) cycloaddition with furan. The regiochemistry of the [2 + 2] cycloadducts is independent of the substitution of the unsaturated component and of the oxidation state of the cephalosporin sulfur atom. However in the case of the [4 + 2] adducts, the sulfur oxidation state determines the regiochemistry of the addition. Carbacephalosporins also participate in this reaction with olefins but require a stronger base such as DBU. Thus the reaction described provides a facile, one-step procedure for the production of a rich variety of novel polycyclic cephalosporins.

  DOI：

  10.1021/jo970176s

文献信息

• Cycloadditions of cephalosporins. The formation of [4+2] adducts with 5-membered heterocycles
  作者：Richard L. Elliott、Neville H. Nicholson、Fiona E. Peaker、Andrew K. Takle、John W. Tyler、Janet White

  DOI：10.1021/jo00086a007

  日期：1994.4

  The cephalosporin triflate 1, and its sulfoxides 4 and 5, react with furan in the presence of a base to give [4 + 2] cycloadducts; the regiochemistry of the addition is determined by the oxidation state of the cephalosporin.
• US5578592A
  申请人：——

  公开号：US5578592A

  公开（公告）日：1996-11-26