(8S,8aS)-8-((bromomethyl)dimethylsilyloxy)-2-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione | 1001166-66-0

• 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: (8S,8aS)-8-((bromomethyl)dimethylsilyloxy)-2-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• 英文别名: (8S,8aS)-8-[bromomethyl(dimethyl)silyl]oxy-2-methyl-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 1001166-66-0
• 化学式: C₁₁H₁₉BrN₂O₃Si
• 分子量: 335.273
• InChiKey: SDMQYQKBFHJTID-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,8aS)-8-((bromomethyl)dimethylsilyloxy)-2-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione 、 copper diacetate 在 偶氮二异丁腈 、 三(三甲基硅基)硅烷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.67h， 以30%的产率得到[(8S)-2-methyl-1,4-dioxo-8-trimethylsilyloxy-3,6,7,8-tetrahydropyrrolo[1,2-a]pyrazin-8a-yl] acetate
  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：

  溴甲基二甲基氯硅烷 、 (8S,8aS)-8-hydroxy-2-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以54%的产率得到(8S,8aS)-8-((bromomethyl)dimethylsilyloxy)-2-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
  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

文献信息

• Construction of Epidithiodioxopiperazines by Directed Oxidation of Hydroxyproline-Derived Dioxopiperazines
  作者：Larry E. Overman、Takaaki Sato

  DOI：10.1021/ol702518t

  日期：2007.12.1

  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.