[(5R)-3,3-dimethyl-7-oxo-6t-(2-phenyl-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2c-yl]-carbamic acid 2,2,2-trichloro-ethyl ester | 26531-12-4

• 英文名称: [(5R)-3,3-dimethyl-7-oxo-6t-(2-phenyl-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2c-yl]-carbamic acid 2,2,2-trichloro-ethyl ester
• 英文别名: 2,2,2-trichloroethyl N-[(2R,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbamate
• CAS: 26531-12-4
• 化学式: C₁₈H₂₀Cl₃N₃O₄S
• 分子量: 480.799
• InChiKey: SZBOSAWQTVKDME-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.74
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(5R)-3,3-dimethyl-7-oxo-6t-(2-phenyl-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2c-yl]-carbamic acid 2,2,2-trichloro-ethyl ester 在 chromium dichloride 、 五氯化磷 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R)-4,4-dimethyl-(1rH,6cH)-5-thia-2,7-diaza-bicyclo[4.2.0]oct-2-en-8-one
  参考文献：
  名称：

  [来自青霉素的新的内酰胺系统]。

  摘要：

  Abstract3‐Isopropyl‐4‐thia‐2,6‐diazabicyclo[3.2.0]heptan‐7‐on (8), a potential intermediate for the synthesis of new β‐lactam antibiotics [5], was prepared from the urethanes 7a and 9 by reduction with zinc/acetic acid. The cyclic Schiff base 10, which constitutes an intermediate in this reaction, was prepared by reduction of 9 with CrCl2 and was further reduced to 8 with zinc/acetic acid.

  DOI：

  10.1002/hlca.19720550211
• 作为产物：
  描述：

  6β-(2-phenyl-acetylamino)-penicillanic acid; triethylamine salt 生成 [(5R)-3,3-dimethyl-7-oxo-6t-(2-phenyl-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2c-yl]-carbamic acid 2,2,2-trichloro-ethyl 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