methyl (1R,6R)-13-methyl-3-(4-methylphenyl)sulfonyl-2,8,12-trioxo-11-oxa-3,13-diazatricyclo[8.5.0.01,6]pentadecane-14-carboxylate | 130291-53-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,6R)-13-methyl-3-(4-methylphenyl)sulfonyl-2,8,12-trioxo-11-oxa-3,13-diazatricyclo[8.5.0.01,6]pentadecane-14-carboxylate
• CAS: 130291-53-1
• 化学式: C₂₂H₂₆N₂O₈S
• 分子量: 478.523
• InChiKey: OZVVDQRFHFTOCG-UMPJGFJBSA-N

物化性质

• 沸点：
  704.1±70.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  127.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  8a-<2-(Methoxycarbonyl)-2-ethyl>-2-(p-toluenesulfonyl)-cis-1,2,3,4,4a,5,6,8a-octahydro-1,6-dioxoisoquinoline 在 碘代三甲硅烷 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以57%的产率得到methyl (1R,6R)-13-methyl-3-(4-methylphenyl)sulfonyl-2,8,12-trioxo-11-oxa-3,13-diazatricyclo[8.5.0.01,6]pentadecane-14-carboxylate
  参考文献：
  名称：

  关于manzamine a II的合成研究；吡咯并[2,3-j]异喹啉骨架的新颖狄尔斯-阿尔德方法

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)94730-0

文献信息

• 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.
• TORISAWA, YASUHIRO;NAKAGAWA, MASAKO;ARAI, HITOE;LAI, ZIPING;HINO, TOHRU;N+, TETRAHEDRON LETT., 31,(1990) N2, C. 3195-3198
  作者：TORISAWA, YASUHIRO、NAKAGAWA, MASAKO、ARAI, HITOE、LAI, ZIPING、HINO, TOHRU、N+

  DOI：——

  日期：——