(5R)-N,N'-Dimethyl-3,3-dimethyl-6b-(phthalimido)-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2α-carboxamide

• 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: (5R)-N,N'-Dimethyl-3,3-dimethyl-6b-(phthalimido)-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2α-carboxamide
• 英文别名: (5R)-N,N'-Dimethyl-3,3-dimethyl-6b-(phthalimido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2α-carboxamide；(2S,5R,6R)-6-(1,3-dioxoisoindol-2-yl)-N,N,3,3-tetramethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxamide
• 化学式: C₁₈H₁₉N₃O₄S
• 分子量: 373.433
• InChiKey: XAFUSTMUKZQTNW-BWACUDIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N-二甲基三甲基硅胺 、 6-β-phthalimidopenicillanic acid 在 2,2'-二硫二吡啶 、 三丁基膦 作用下， 生成 (5R)-N,N'-Dimethyl-3,3-dimethyl-6b-(phthalimido)-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2α-carboxamide
  参考文献：
  名称：

  Synthesis of amides: An efficient and chemoselective method for the preparation of β-lactam derivatives related to HLE inhibitors

  摘要：

  A practical method for the chemoselective synthesis of amides in presence of the beta-lactam ring has been described, by an efficient coupling reaction between a reactive 2-pyridyl thiolester intermediate and a suitable N-silylamine.

  DOI：

  10.1016/s0040-4020(01)80373-2

文献信息

• Synthesis of amides: An efficient and chemoselective method for the preparation of β-lactam derivatives related to HLE inhibitors
  作者：Romano Di Fabio、Vincenzo Summa、Tino Rossi

  DOI：10.1016/s0040-4020(01)80373-2

  日期：1993.3

  A practical method for the chemoselective synthesis of amides in presence of the beta-lactam ring has been described, by an efficient coupling reaction between a reactive 2-pyridyl thiolester intermediate and a suitable N-silylamine.