(2S,5R,6R)-3-Chloromethyl-3-methyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester | 93061-18-8

• 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: (2S,5R,6R)-3-Chloromethyl-3-methyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
• CAS: 93061-18-8
• 化学式: C₁₇H₁₉ClN₂O₄S
• 分子量: 382.868
• InChiKey: OZQJAIJJLDBKSQ-AXLMJIKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  methyl (2R)-<(3S,4R)-4-(benzothiazol-2-yldithio)-2-oxo-3-phenylacetamidoazetidin-1-yl>-3-methylbut-3-enoate 在 magnesium chloride 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 以66%的产率得到(2S,5R,6R)-3-Chloromethyl-3-methyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl 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