p-Methoxybenzyl (4S,5S,6S,8R,9R)-4,5-dimethyl-10-oxo-9-phenylacetamido-7-thia-1-azatricyclo[6.2.0.03,6 ]dec-2-ene-2-carboxylate | 152999-62-7

• 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 (4S,5S,6S,8R,9R)-4,5-dimethyl-10-oxo-9-phenylacetamido-7-thia-1-azatricyclo[6.2.0.03,6 ]dec-2-ene-2-carboxylate
• 英文别名: p-Methoxybenzyl (4S,5S,6S,8R,9R)-4,5-dimethyl-10-oxo-9-phenylacetamido-7-thia-1-azatricyclo[6.2.0.03,6]dec-2-ene-2-carboxylate；(4-methoxyphenyl)methyl (4S,5S,6S,8R,9R)-4,5-dimethyl-10-oxo-9-[(2-phenylacetyl)amino]-7-thia-1-azatricyclo[6.2.0.03,6]dec-2-ene-2-carboxylate
• CAS: 152999-62-7
• 化学式: C₂₇H₂₈N₂O₅S
• 分子量: 492.596
• InChiKey: DIECHFITOBEPGH-XSMPCZQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-Methoxybenzyl (4S,5S,6S,8R,9R)-4,5-dimethyl-10-oxo-9-phenylacetamido-7-thia-1-azatricyclo[6.2.0.03,6 ]dec-2-ene-2-carboxylate 以60%的产率得到Sodium (4R,5S,6S,8R,9R)-4,5-dimethyl-10-oxo-9-phenylacetamido-7-thia-1-azatricyclo[6.2.0.03,6 ]dec-2-ene-2-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：

  反-2-丁烯 、 (7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到p-Methoxybenzyl (4S,5S,6S,8R,9R)-4,5-dimethyl-10-oxo-9-phenylacetamido-7-thia-1-azatricyclo[6.2.0.03,6 ]dec-2-ene-2-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

文献信息

• 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
  作者：Richard L. Elliott、Neville H. Nicholson、Fiona E. Peaker、Andrew K. Takle、Christine M. Richardson、John W. Tyler、Janet White、Michael J. Pearson、Drake S. Eggleston、R. Curtis Haltiwanger

  DOI：10.1021/jo970176s

  日期：1997.7.1

  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.
• Cycloadditions of cephalosporins. A general synthesis of novel 2,3-fused cyclobutane and cyclobutene cephems
  作者：Richard L. Elliott、Andrew K. Takle、John W. Tyler、Janet White

  DOI：10.1021/jo00077a007

  日期：1993.12

  The cephalosporin triflate (1) reacts with a wide variety of olefins and acetylenes in the presence of a base to give 2,3-fused cyclobutane and cyclobutene derivatives, respectively.
• Cephalosporin derivatives
  申请人：Pfizer Inc.

  公开号：US05578592A1

  公开（公告）日：1996-11-26

  Compounds of formula (I) or salts thereof: wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group; CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion, or R.sup.3 is a readily removable carboxy protecting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently represent hydrogen or a bond or a substituent group or may form a cyclic system. These compounds have antibacterial activity.

  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。