(2R,4S)-2-((R)-Hydroxycarbamoyl-phenylacetylamino-methyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid benzyl ester | 104430-19-5

• 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,4S)-2-((R)-Hydroxycarbamoyl-phenylacetylamino-methyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid benzyl ester
• CAS: 104430-19-5
• 化学式: C₂₃H₂₇N₃O₅S
• 分子量: 457.55
• InChiKey: IDNPONPVKJEVPJ-SVFBPWRDSA-N

物化性质

• 密度：
  1.272±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  116.76
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2-((R)-Hydroxycarbamoyl-phenylacetylamino-methyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid benzyl ester 在 1-(二乙氨基)丙炔 作用下， 以 二氯甲烷 为溶剂， 以7 g的产率得到(3S,7R,7aR)-2,2-Dimethyl-5-oxo-7-phenylacetylamino-hexahydro-imidazo[5,1-b]thiazole-3-carboxylic acid benzyl ester
  参考文献：
  名称：

  Ring Enlargement of the β-Lactam Nucleus of Penicillins

  摘要：

  AbstractUsing penicillins as starting materials, a general synthetic route to the bicyclic compounds 7 has been established; they formally result from a ring enlargement of the ß‐lactam with insertion of one nitrogen atom. The key‐step of the procedure is a very mild Lossen rearrangement of hydroxamic acids intermediates upon treatment with N,N‐diethylaminopropyne.

  DOI：

  10.1002/bscb.19850941123
• 作为产物：
  描述：

  penicillin G benzyl ester 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 以100%的产率得到(2R,4S)-2-((R)-Hydroxycarbamoyl-phenylacetylamino-methyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid benzyl ester
  参考文献：
  名称：

  Ring Enlargement of the β-Lactam Nucleus of Penicillins

  摘要：

  AbstractUsing penicillins as starting materials, a general synthetic route to the bicyclic compounds 7 has been established; they formally result from a ring enlargement of the ß‐lactam with insertion of one nitrogen atom. The key‐step of the procedure is a very mild Lossen rearrangement of hydroxamic acids intermediates upon treatment with N,N‐diethylaminopropyne.

  DOI：

  10.1002/bscb.19850941123