(R)-3-Chloromethyl-2-[(3R,4R)-2-oxo-4-pentachlorophenyldisulfanyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid benzyl ester | 83242-33-5

• 英文名称: (R)-3-Chloromethyl-2-[(3R,4R)-2-oxo-4-pentachlorophenyldisulfanyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid benzyl ester
• CAS: 83242-33-5
• 化学式: C₂₉H₂₂Cl₆N₂O₅S₂
• 分子量: 755.354
• InChiKey: VNRNJYKWEBZJFG-INNMJMHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-3-Chloromethyl-2-[(3R,4R)-2-oxo-4-pentachlorophenyldisulfanyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid benzyl ester 在 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到(6R,7R)-8-Oxo-3-pentachlorophenylsulfanylmethyl-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Penicillin-cephalosporin conversion IV. Direct synthesis of 3'-thiosubstituted cephalosporins from thiazoline-azetidinones

  摘要：

  DOI：

  10.1016/s0040-4039(00)87378-5
• 作为产物：
  描述：

  pentachlorophenylsulphenyl chloride 、 (R)-3-chloromethyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzyl ester 在 盐酸 作用下， 以74%的产率得到(R)-3-Chloromethyl-2-[(3R,4R)-2-oxo-4-pentachlorophenyldisulfanyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-but-3-enoic acid benzyl ester
  参考文献：
  名称：

  Prominent Aspects of Electroorganic Synthesis in β-Lactam Chemistry

  摘要：

  AbstractThe potentiality of electrolysis procedures in the penicillin‐cephalosporin conversion as well as in the direct transform of penicillins into oxazolineazetidinones as an intermediate for the preparation of the sulfur‐free analogues of cephalosporins are discussed. Especially, a chemoselective electrolytic chlorination of methyl group of 3‐methyl‐3‐butenoate moiety of thiazolineazetidinone derived from penicillins, a direct synthesis of 3′‐thiosubstituted cephalosporins from the thiazoline‐azetidinones, an improved synthesis of exomethylenecephams, an efficient route to 3‐chloromethyl‐Δ3‐cephems, electrochemical S‐S bond fission of 4‐(2‐benzothiazolyldithio) azetidinones, a direct transformation of penicillins into oxazoline‐azetidinones by chloride salt‐promoted electrolysis, and a versatile intermediate for new β‐lactam antibiotics are presented.

  DOI：

  10.1002/bscb.19820911202