benzyl (6R,7R)-3-(chloromethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 82895-21-4

• 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: benzyl (6R,7R)-3-(chloromethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 82895-21-4
• 化学式: C₂₃H₂₁ClN₂O₄S
• 分子量: 456.95
• InChiKey: BRGVJMZBNVOQGN-DENIHFKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl (6R,7R)-3-(chloromethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 、 2-巯基-5-甲基-1,3,4-噻二唑 在 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  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：

  benzyl (2S)-2-[(2R,3R)-2-(benzenesulfonylsulfanyl)-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-(chloromethyl)but-3-enoate 生成 benzyl (6R,7R)-3-(chloromethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  TORIJ, SIGEHSI;TANAKA, XIDEHO;NOKAMI, DZYUNDZO;SASAOKA, MITIO;SAJTO, NORI+

  摘要：

  DOI：

文献信息

• Penicillin–Cephalosporin Conversion. XII. Electroreductive Dechlorination of 3′-Chlorocephalosporins into 3-Methylenecephams
  作者：Sigeru Torii、Hideo Tanaka、Toshiyuki Ohshima、Michio Sasaoka

  DOI：10.1246/bcsj.59.3975

  日期：1986.12

  An efficient electroreductive conversion of 3′-chlorocephalosporins and their analogues into the corresponding 3-methylenecephams has been performed in an aqueous THF–LiClO4–(Pb cathode) and/or aqueous MeCN–EtOH–LiClO4–NH4ClO4 (Pb cathode) system.

  在水性 THF-LiClO4-（Pb 阴极）和/或水性 MeCN-EtOH-LiClO4-NH4ClO4（Pb 阴极）系统中，将 3'-氯头孢菌素及其类似物有效电还原转化为相应的 3-亚甲基头孢菌素。
• 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.
• TORII, SUGERU;UNEYAMA, KENJI;TANAKA, HIDEO;NOKAMI, JUNZO;SASAOKA, MICHIO;+
  作者：TORII, SUGERU、UNEYAMA, KENJI、TANAKA, HIDEO、NOKAMI, JUNZO、SASAOKA, MICHIO、+

  DOI：——

  日期：——