(6R)-3-methoxycarbonylmethylsulfanyl-5ξ,8-dioxo-7t-(2-phenyl-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester | 59780-01-7

• 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: (6R)-3-methoxycarbonylmethylsulfanyl-5ξ,8-dioxo-7t-(2-phenyl-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• 英文别名: benzhydryl (6R,7R)-3-(2-methoxy-2-oxoethyl)sulfanyl-5,8-dioxo-7-[(2-phenylacetyl)amino]-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；benzhydryl (6R,7R)-3-(2-methoxy-2-oxoethyl)sulfanyl-5,8-dioxo-7-[(2-phenylacetyl)amino]-5λ4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 59780-01-7
• 化学式: C₃₁H₂₈N₂O₇S₂
• 分子量: 604.705
• InChiKey: NQQIYXGVVTUHAE-ZPCAGIKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (6R)-3-methoxycarbonylmethylsulfanyl-5ξ,8-dioxo-7t-(2-phenyl-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 三氯化磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (6R)-3-methoxycarbonylmethylsulfanyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  Neue ?-Lactam-Antibiotika. �ber die Funktionalisierung der Cephem-3-Stellung mittels Schwefel oder Stickstoff. Modifikationen von Antibiotika, 13. Mitteilung

  摘要：

  New β‐lactam antibiotics. Functionalisation of the cephem 3‐position with sulfur or nitrogen bearing substituentsThe tosylate sulfoxides or mesylates derived from the 3‐hydroxy‐ceph‐3‐em esters 1a, b reacted with thiols to give 3‐thioethers which were converted into the microbiologically active acids 7a, c, 8a, c 9c, and 13c by known procedures. The 3‐methylsulfonyl‐derivative 17c was prepared from 6b. The synthesis of the 3‐acylamino‐ceph‐3‐em‐4‐carboxylic acids 23c and 24c is reported.

  DOI：

  10.1002/hlca.19750580824
• 作为产物：
  描述：

  3-羟基头孢 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (6R)-3-methoxycarbonylmethylsulfanyl-5ξ,8-dioxo-7t-(2-phenyl-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  Neue ?-Lactam-Antibiotika. �ber die Funktionalisierung der Cephem-3-Stellung mittels Schwefel oder Stickstoff. Modifikationen von Antibiotika, 13. Mitteilung

  摘要：

  New β‐lactam antibiotics. Functionalisation of the cephem 3‐position with sulfur or nitrogen bearing substituentsThe tosylate sulfoxides or mesylates derived from the 3‐hydroxy‐ceph‐3‐em esters 1a, b reacted with thiols to give 3‐thioethers which were converted into the microbiologically active acids 7a, c, 8a, c 9c, and 13c by known procedures. The 3‐methylsulfonyl‐derivative 17c was prepared from 6b. The synthesis of the 3‐acylamino‐ceph‐3‐em‐4‐carboxylic acids 23c and 24c is reported.

  DOI：

  10.1002/hlca.19750580824

文献信息

• US4256739A
  申请人：——

  公开号：US4256739A

  公开（公告）日：1981-03-17