rac-Methyl (2S^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate | 143167-08-2

• 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 (2S^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate
• 英文别名: methyl (4aS,7aS,9R,10aS)-8-methyl-2-(4-methylphenyl)sulfonyl-1,6-dioxo-3,4,4a,5,7,7a,9,10-octahydropyrrolo[2,3-i]isoquinoline-9-carboxylate
• CAS: 143167-08-2
• 化学式: C₂₁H₂₆N₂O₆S
• 分子量: 434.513
• InChiKey: PHDABQBNSSNJTG-NFQYFHPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  101.06
• 氢给体数：
  0.0
• 氢受体数：
  7.0

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 、 碳酸氢钠 、 potassium carbonate 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 98.58h， 生成 rac-Methyl (2S^*,3aS^*,6aS^*,10aS^*)-3-methyl-5,10-dioxo-9-(p-toluenesulfonyl)-1,2,3,3a,4,5,6,6a,7,8,9,10-dodecahydropyrrolo<2,3-i>isoquinoline-2-carboxylate
  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

文献信息

• Synthetic studies on manzamine a II; a novel diels-alder approach to the pyrrolo[2,3-j]isoquinoline skeleton
  作者：Yasuhiro Torisawa、Masako Nakagawa、Hitoe Arai、Ziping Lai、Tohru Hino、Tadashi Nakata、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)94730-0

  日期：1990.1

  An expeditious preparation of the central pyrroloisoquinoline skeleton of manzamine A (I) was achieved via the high-pressure Diels-Alder reaction of 3-alkyl-5,6-dihydro-2-pyridinone (10) with Danishefsky diene followed by deprotection and spontaneous pyrrolidine ring clousure.

  通过3-烷基-5,6-二氢-2-吡啶酮（1 0）与Danishefsky二烯的高压Diels-Alder反应，然后进行脱保护和保护，可以快速制备曼扎明A（I）的中心吡咯并异喹啉骨架。自发性吡咯烷环闭合。
• Diels-Alder reactions of dihydropyridinones: synthetic entry to the manzamine A tricyclic core
  作者：Yasuhiro Torisawa、Masako Nakagawa、Toshihiro Hosaka、Kiyoshi Tanabe、Ziping Lai、Koreharu Ogata、Tadashi Nakata、Takeshi Oishi、Tohru Hino

  DOI：10.1021/jo00047a031

  日期：1992.10

  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.