(2R)-2-[(1R,5R)-3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl]-3-methylbut-3-enoic acid | 91177-12-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R)-2-[(1R,5R)-3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl]-3-methylbut-3-enoic acid
• CAS: 91177-12-7
• 化学式: C₁₆H₁₆N₂O₃S
• 分子量: 316.381
• InChiKey: AMGXDNLTAXLYNP-UMVBOHGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(1R,5R)-3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl]-3-methylbut-3-enoic acid 在 sodium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 生成 (1E,5R)-3-Phenylmethyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-one
  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
• 作为产物：
  描述：

  penicillin G 1-oxide 在 三丁基,三丁酯 作用下， 以 甲苯 为溶剂， 反应 40.33h， 生成 (2R)-2-[(1R,5R)-3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl]-3-methylbut-3-enoic acid
  参考文献：
  名称：

  甲硅烷基化青霉素G 1-氧化物的还原性重排

  摘要：

  青霉素G 1-氧化物与BSU的反应，然后用亚磷酸三丁酯处理，水解后得到结晶的噻唑啉氮杂环丁酮2。还原后加入三乙胺导致噻唑啉氮杂环丁酮3异构体的形成。

  DOI：

  10.1016/s0040-4039(00)78473-5

文献信息

• TANAKA, HIDEO;TANIGUCHI, MASATOSHI;NODA, YOSHIAKI;KAMEYAMA, YUTAKA;SASAOK+, CHEM. EXPRESS., 5,(1990) N1, C. 873-876
  作者：TANAKA, HIDEO、TANIGUCHI, MASATOSHI、NODA, YOSHIAKI、KAMEYAMA, YUTAKA、SASAOK+

  DOI：——

  日期：——
• 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.
• Reductive rearrangements of silylated penicillin G 1-oxide
  作者：Pieter A.M. van der Klein、Henk A. Witkamp、Erik de Vroom

  DOI：10.1016/s0040-4039(00)78473-5

  日期：1994.11

  The reaction of penicillin G 1-oxide with BSU followed by treatment with tributyl phosphite gives, after hydrolysis, crystalline thiazoline azetidinone 2. Addition of triethylamine after reduction resulted in the formation of the isomeric thiazoline azetidinone 3.

  青霉素G 1-氧化物与BSU的反应，然后用亚磷酸三丁酯处理，水解后得到结晶的噻唑啉氮杂环丁酮2。还原后加入三乙胺导致噻唑啉氮杂环丁酮3异构体的形成。