(1R)-3,3-dimethyl-7-oxo-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]heptane-2-carbonyl chloride | 26532-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1R)-3,3-dimethyl-7-oxo-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]heptane-2-carbonyl chloride
• 英文别名: 3-Chlorcarbonyl-4,4-dimethylazetidino<3,2-d>thiazolidin-2-on；(1R)-3,3-dimethyl-7-oxo-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]heptane-2-carbonyl chloride
• CAS: 26532-34-3
• 化学式: C₇H₉ClN₂O₂S
• 分子量: 220.68
• InChiKey: QJBFSLJZTYQAQH-NQXXGFSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R)-3,3-dimethyl-7-oxo-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]heptane-2-carbonyl chloride 在 calcium carbonate 作用下， 以 吡啶 为溶剂， 生成 (1R)-6-acetyl-3,3-dimethyl-7-oxo-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  青霉素向头孢菌素的转化

  摘要：

  AbstractA new method for the degradation of the thiazolidine ring in penicillins is described. Penicillin V (8a), penicillin G (8b) and 6‐t‐butoxycarbonylaminopenicillanic acid (33) (BOC‐6‐APA) were converted via their acylazides and isocyanates (10 and 34) into 2,2,2‐trichloroethyl urethanes (11 and 35). Reductive removal of the trichloroethoxycarbonyl groups in an aqueous medium gave the 3‐hydroxy‐penam‐derivatives 13 and 36. The structure and various reactions of these carbinolamides are discussed in detail. An oxidative radical fragmentation (using lead tetraacylates and light) followed by thermal treatment transformed the 3‐hydroxy‐penam‐derivatives into the N‐formyl‐β‐lactam‐thio‐enolethers 27 and 37 in which the formyl group could be replaced by hydrogen. Reactions of the β‐lactam and thio‐enolether functions are described.The BOC‐derivative 37 can be transformed into the isomeric compound 3, an intermediate in Woodward's total synthesis of cephalosporins.

  DOI：

  10.1002/hlca.19720550209
• 作为产物：
  描述：

  2α-Isopropenylmercapto-3α-(N-carbo-tert.-butyloxyamino)-azetidin-4-on 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (1R)-3,3-dimethyl-7-oxo-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]heptane-2-carbonyl chloride
  参考文献：
  名称：

  青霉素向头孢菌素的转化

  摘要：

  AbstractA new method for the degradation of the thiazolidine ring in penicillins is described. Penicillin V (8a), penicillin G (8b) and 6‐t‐butoxycarbonylaminopenicillanic acid (33) (BOC‐6‐APA) were converted via their acylazides and isocyanates (10 and 34) into 2,2,2‐trichloroethyl urethanes (11 and 35). Reductive removal of the trichloroethoxycarbonyl groups in an aqueous medium gave the 3‐hydroxy‐penam‐derivatives 13 and 36. The structure and various reactions of these carbinolamides are discussed in detail. An oxidative radical fragmentation (using lead tetraacylates and light) followed by thermal treatment transformed the 3‐hydroxy‐penam‐derivatives into the N‐formyl‐β‐lactam‐thio‐enolethers 27 and 37 in which the formyl group could be replaced by hydrogen. Reactions of the β‐lactam and thio‐enolether functions are described.The BOC‐derivative 37 can be transformed into the isomeric compound 3, an intermediate in Woodward's total synthesis of cephalosporins.

  DOI：

  10.1002/hlca.19720550209