8a-Methyl-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline | 143076-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 8a-Methyl-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline
• CAS: 143076-11-3
• 化学式: C₁₇H₁₉NO₄S
• 分子量: 333.408
• InChiKey: YQGIIHQENWTQPF-SUMWQHHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.52
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-(toluene-4-sulfonyl)piperidin-2-one 在 camphor-10-sulfonic acid 、 双(三甲基硅烷基)氨基钾 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.75h， 生成 8a-Methyl-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline
  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。