[6R-[3(E),6α,7β]]-3-[(1-Cyclopropyl-2-oxo-3-pyrrolidinylidene)-methyl]-7-[[(1,1-dimethylethoxy)carbonyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester | 161675-43-0

• 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-[3(E),6α,7β]]-3-[(1-Cyclopropyl-2-oxo-3-pyrrolidinylidene)-methyl]-7-[[(1,1-dimethylethoxy)carbonyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester
• 英文别名: [6R-[3(E)-6R,7R]]-3-[(1-cyclopropyl-2-oxo-3-pyrrolidinylidene)methyl]-7-[[(1,1-dimethylethoxy)carbonyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester；benzhydryl (6R,7R)-3-[(Z)-(1-cyclopropyl-2-oxopyrrolidin-3-ylidene)methyl]-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 161675-43-0
• 化学式: C₃₃H₃₅N₃O₆S
• 分子量: 601.723
• InChiKey: UKNHMFCJVKAIMD-GQYACGOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 [6R-[3(E),6α,7β]]-3-[(1-Cyclopropyl-2-oxo-3-pyrrolidinylidene)-methyl]-7-[[(1,1-dimethylethoxy)carbonyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester 在 苯甲醚 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-(6R,7R)-7-Amino-3-(1-cyclopropyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid trifluoroacetate
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of (Lactamylvinyl)cephalosporins Exhibiting Activity against Staphylococci, Pneumococci, and Enterococci

  摘要：

  The synthesis and structure-activity relationships of a new class of vinylcephalosporins substituted with a lactamyl residue (1) are described. These compounds show excellent activity against enterococci and retain the broad spectrum activity of third-generation cephalosporins such as ceftriaxone.

  DOI：

  10.1021/jm950886v
• 作为产物：
  描述：

  (6R,7R)-7-tert-Butoxycarbonylamino-3-[1-cyclopropyl-2-oxo-pyrrolidin-(3Z)-ylidenemethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 三溴化磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [6R-[3(E),6α,7β]]-3-[(1-Cyclopropyl-2-oxo-3-pyrrolidinylidene)-methyl]-7-[[(1,1-dimethylethoxy)carbonyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of (Lactamylvinyl)cephalosporins Exhibiting Activity against Staphylococci, Pneumococci, and Enterococci

  摘要：

  The synthesis and structure-activity relationships of a new class of vinylcephalosporins substituted with a lactamyl residue (1) are described. These compounds show excellent activity against enterococci and retain the broad spectrum activity of third-generation cephalosporins such as ceftriaxone.

  DOI：

  10.1021/jm950886v

文献信息

• Process for producing cephalosporin derivatives
  申请人：Basilea Pharmaceutica AG

  公开号：US06384214B1

  公开（公告）日：2002-05-07

  The present invention is concerned with a novel process for the manufacture of cephalosporin derivatives of the formula by converting a phosphonium salt into the corresponding ylide and reacting same with an aldehyde wherein R1 and R2 are as above.

  本发明涉及一种新颖的制备头孢菌素衍生物的工艺，通过将磷酸铵盐转化为相应的叶烯，并将其与醛反应，其中R1和R2如上所述。