rac-Methyl (2R^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate 5-ethylene ketal | 143076-19-1

• 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: rac-Methyl (2R^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate 5-ethylene ketal
• CAS: 143076-19-1
• 化学式: C₁₆H₂₄N₂O₅
• 分子量: 324.377
• InChiKey: YFLDGZCMTBMLJV-YWDSYVAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  77.1
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-(toluene-4-sulfonyl)piperidin-2-one 在 18-冠醚-6 、 camphor-10-sulfonic acid 、 双(三甲基硅烷基)氨基钾 、 sodium naphthalenide 、 碳酸氢钠 、 potassium carbonate 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 111.58h， 生成 rac-Methyl (2R^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate 5-ethylene ketal
  参考文献：
  名称：

  Diels-Alder reactions of dihydropyridinones: synthetic entry to the manzamine A tricyclic core

  摘要：

  For the construction of the tricyclic core of manzamine A (1), the Diels-Alder reactions of some dihydropyridinones were surveyed. The N-protecting group of the dihydropyridinone played an important role in achieving a successful Diels-Alder reaction. In view of its electron-withdrawing character as well as its thermal stability, the p-toluenesulfonyl protecting group was found to be best in our synthesis. An effective method for the preparation of 3-alkyldihydropyridinones via the Michael addition to dehydroalanine derivatives has also been devised. By the utilization of a high-pressure Diels-Alder reaction of the N-tosyl-3-alkyldihydropyridinone (17) with the Danishefsky diene, a facile construction of the central pyrroloisoquinoline skeleton (21) was successfully achieved.

  DOI：

  10.1021/jo00047a031