Ioehhukouvmzke-qghzaeeisa- | 135446-51-4

• 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: Ioehhukouvmzke-qghzaeeisa-
• 英文别名: benzyl (1S,5S,8aS,8bR)-1-[(1R)-1-hydroxyethyl]-5-methoxy-2-oxo-5,6,7,8,8a,8b-hexahydro-1H-azeto[1,2-b]isoindole-4-carboxylate
• CAS: 135446-51-4
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: IOEHHUKOUVMZKE-QGHZAEEISA-N

物化性质

• 沸点：
  572.3±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ioehhukouvmzke-qghzaeeisa- 、 1,2,3,4,4a,5,6,7-八氢-2,2,4a,7,7-五甲基萘啶 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以100%的产率得到
  参考文献：
  名称：

  A Highly Stereoselective and Practical Total Synthesis of the Tricyclic β-Lactam Antibiotic GV104326 (4-Methoxytrinem)

  摘要：

  A novel and practical total synthesis of a tricyclic beta-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the highly diastereoselective synthesis is a protonation of a zinc enolate complex which circumvents the use of enantiomerically pure (S)-2-methoxycyclohexanone. A mechanistic rationale is presented and experimentally verified.

  DOI：

  10.1021/ja962006n
• 作为产物：
  描述：

  2-甲氧基环己酮 在 吡啶 、 2,6-二甲基吡啶 、 甲酸 、 四丁基氟化铵 、 palladium diacetate 、 potassium hydride 、 sodium hydride 、 溶剂黄146 、 三苯基膦 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 xylene 为溶剂， 反应 131.25h， 生成 Ioehhukouvmzke-qghzaeeisa-
  参考文献：
  名称：

  A Highly Stereoselective and Practical Total Synthesis of the Tricyclic β-Lactam Antibiotic GV104326 (4-Methoxytrinem)

  摘要：

  A novel and practical total synthesis of a tricyclic beta-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the highly diastereoselective synthesis is a protonation of a zinc enolate complex which circumvents the use of enantiomerically pure (S)-2-methoxycyclohexanone. A mechanistic rationale is presented and experimentally verified.

  DOI：

  10.1021/ja962006n

文献信息

• A Highly Stereoselective and Practical Total Synthesis of the Tricyclic β-Lactam Antibiotic GV104326 (4-Methoxytrinem)
  作者：Stephen Hanessian、Michael J. Rozema

  DOI：10.1021/ja962006n

  日期：1996.1.1

  A novel and practical total synthesis of a tricyclic beta-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the highly diastereoselective synthesis is a protonation of a zinc enolate complex which circumvents the use of enantiomerically pure (S)-2-methoxycyclohexanone. A mechanistic rationale is presented and experimentally verified.