(3R,8S,8aS)-8a-hydroxy-2-methyl-1,4-dioxo-8-(trimethylsilyloxy)octahydropyrrolo[1,2-a]pyrazin-3-yl ethanoate | 1001166-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (3R,8S,8aS)-8a-hydroxy-2-methyl-1,4-dioxo-8-(trimethylsilyloxy)octahydropyrrolo[1,2-a]pyrazin-3-yl ethanoate
• 英文别名: [(3R,8S,8aS)-8a-hydroxy-2-methyl-1,4-dioxo-8-trimethylsilyloxy-3,6,7,8-tetrahydropyrrolo[1,2-a]pyrazin-3-yl] acetate
• CAS: 1001166-70-6
• 化学式: C₁₃H₂₂N₂O₆Si
• 分子量: 330.413
• InChiKey: KKTYIWVQANPAIL-NDMJEZRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.51
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,8S,8aS)-8a-hydroxy-2-methyl-1,4-dioxo-8-(trimethylsilyloxy)octahydropyrrolo[1,2-a]pyrazin-3-yl ethanoate 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以77%的产率得到(3R,8S,8aS)-2-methyl-1,4-dioxo-8-(trimethylsilyloxy)octahydropyrrolo[1,2-a]pyrazine-3,8-diyl diethanoate
  参考文献：
  名称：

  Construction of Epidithiodioxopiperazines by Directed Oxidation of Hydroxyproline-Derived Dioxopiperazines

  摘要：

  Functionalization of the angular methine carbon of hydroxyproline-derived dioxopiperazines by a radical-promoted C-H bond oxidation, which is directed by a proximal (bromomethyl)silyl group, is described. This regioselective oxidation is the key step in a new synthesis of epidithiodioxopiperazines.

  DOI：

  10.1021/ol702518t
• 作为产物：
  描述：

  (3R,8S,8aS)-8-((bromomethyl)dimethylsilyloxy)-2-methyl-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl ethanoate 、 copper diacetate 在 偶氮二异丁腈 、 三(三甲基硅基)硅烷 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以42%的产率得到(3R,8S,8aS)-2-methyl-1,4-dioxo-8-(trimethylsilyloxy)octahydropyrrolo[1,2-a]pyrazine-3,8-diyl diethanoate
  参考文献：
  名称：

  Construction of Epidithiodioxopiperazines by Directed Oxidation of Hydroxyproline-Derived Dioxopiperazines

  摘要：

  Functionalization of the angular methine carbon of hydroxyproline-derived dioxopiperazines by a radical-promoted C-H bond oxidation, which is directed by a proximal (bromomethyl)silyl group, is described. This regioselective oxidation is the key step in a new synthesis of epidithiodioxopiperazines.

  DOI：

  10.1021/ol702518t