2-((1S,5R)-3-Benzyl-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-2-enoic acid benzyl ester | 57518-28-2

• 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: 2-((1S,5R)-3-Benzyl-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-2-enoic acid benzyl ester
• 英文别名: (1S, 5R)-6-(1-benzyloxycarbonyl-2-methyl-1-propenyl)-3-benzyl-4-oxa-2,6-diazabicyclo-[3.2.0]hept-2-en-7-one；benzyl 2-[(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl]-3-methylbut-2-enoate
• CAS: 57518-28-2
• 化学式: C₂₃H₂₂N₂O₄
• 分子量: 390.439
• InChiKey: GVRKJCPHRJGRPN-DENIHFKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  penicillin G benzyl ester 在 magnesium chloride 作用下， 以 甲醇 、 叔丁醇 为溶剂， 以65%的产率得到2-((1S,5R)-3-Benzyl-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-2-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

文献信息

• Process for preparing oxazolineazetidinone derivatives
  申请人：Otsuka Kagaku Yakuhin Kabushiki Kaisha

  公开号：US04379032A1

  公开（公告）日：1983-04-05

  This invention provides a process for preparing an oxazolineazetidinone derivative represented by the formula ##STR1## (wherein R.sup.1 represents hydrogen atom, alkyl group, alkenyl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted aryloxymethyl group, R.sup.2 represents free or protected carboxyl group and R.sup.3 represents hydrogen atom or methoxy group) from a penicillin derivative represented by the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sub.3 are as defined above.

  本发明提供了一种制备由以下式子表示的氧唑啉-氮杂环己酮衍生物的方法：##STR1## （其中 R1代表氢原子、烷基、烯基、取代或未取代的芳基甲基、取代或未取代的芳基、或取代或未取代的芳基氧甲基，R2代表自由或保护的羧基，R3代表氢原子或甲氧基），该方法从以下式子表示的青霉素衍生物中制备：##STR2## 其中R1、R2和R3如上所定义。
• Prominent Aspects of Electroorganic Synthesis in β-Lactam Chemistry
  作者：Sigeru Torii、Hideo Tanaka、Michio Sasaoka、Norio Saitoh、Takashi Siroi、Junzo Nokami

  DOI：10.1002/bscb.19820911202

  日期：——

  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.