(2R,4S)-2-[(R)-Hydroxycarbamoyl-(2-phenoxy-acetylamino)-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester | 104430-21-9

• 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-(2-phenoxy-acetylamino)-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
• CAS: 104430-21-9
• 化学式: C₂₂H₃₁N₃O₈S
• 分子量: 497.569
• InChiKey: VNAIVJWYGYEFKX-SOLBZPMBSA-N

物化性质

• 密度：
  1.267±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  152.29
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2-[(R)-Hydroxycarbamoyl-(2-phenoxy-acetylamino)-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester 在 ynamine 作用下， 以 二氯甲烷 为溶剂， 以410 mg的产率得到(3S,7R,7aR)-2,2-Dimethyl-5-oxo-7-(2-phenoxy-acetylamino)-hexahydro-imidazo[5,1-b]thiazole-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl 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 V potassium 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (2R,4S)-2-[(R)-Hydroxycarbamoyl-(2-phenoxy-acetylamino)-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl 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