(3R,8S,8aS)-8-hydroxy-2-methyl-1,4-dioxohexahydropyrrolo[1,2-a]pyrazine-3,8a(6H)-diyl diacetate | 1001166-76-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (3R,8S,8aS)-8-hydroxy-2-methyl-1,4-dioxohexahydropyrrolo[1,2-a]pyrazine-3,8a(6H)-diyl diacetate
• CAS: 1001166-76-2
• 化学式: C₁₂H₁₆N₂O₇
• 分子量: 300.268
• InChiKey: JQLALWLHOBWTNH-XRNSZHNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  113.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3R,8S,8aS)-8-hydroxy-2-methyl-1,4-dioxohexahydropyrrolo[1,2-a]pyrazine-3,8a(6H)-diyl diacetate 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以100%的产率得到(3R,8S,8aS)-2-methyl-1,4-dioxooctahydropyrrolo[1,2-a]pyrazine-3,8,8a-triyl triethanoate
  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)-2-methyl-1,4-dioxo-8-(trimethylsilyloxy)octahydropyrrolo[1,2-a]pyrazine-3,8-diyl diethanoate 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以98%的产率得到(3R,8S,8aS)-8-hydroxy-2-methyl-1,4-dioxohexahydropyrrolo[1,2-a]pyrazine-3,8a(6H)-diyl diacetate
  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