(3S,7R,7aR)-2,2-Dimethyl-5-oxo-7-phenylacetylamino-hexahydro-imidazo[5,1-b]thiazole-3-carboxylic acid methoxymethyl ester | 104430-25-3

• 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: (3S,7R,7aR)-2,2-Dimethyl-5-oxo-7-phenylacetylamino-hexahydro-imidazo[5,1-b]thiazole-3-carboxylic acid methoxymethyl ester
• CAS: 104430-25-3
• 化学式: C₁₈H₂₃N₃O₅S
• 分子量: 393.464
• InChiKey: KAEXPAUZEPZAFM-RRFJBIMHSA-N

物化性质

• 沸点：
  681.6±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.97
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S,7R,7aR)-2,2-Dimethyl-5-oxo-7-phenylacetylamino-hexahydro-imidazo[5,1-b]thiazole-3-carboxylic acid methoxymethyl ester 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到(3S,7R,7aR)-2,2-Dimethyl-5-oxo-7-phenylacetylamino-hexahydro-imidazo[5,1-b]thiazole-3-carboxylic acid
  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：

  (2R,4S)-2-((R)-Hydroxycarbamoyl-phenylacetylamino-methyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid methoxymethyl ester 在 ynamine 作用下， 以 二氯甲烷 为溶剂， 以2.78 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 methoxymethyl 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