(3S,8S,8aS)-8-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione | 1001166-60-4

• 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: (3S,8S,8aS)-8-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• 英文别名: (3S,8S,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-methyl-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 1001166-60-4
• 化学式: C₁₄H₂₆N₂O₄Si
• 分子量: 314.457
• InChiKey: FOCKJGHKZLJOOI-NHCYSSNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(2-hydroxyethanoyl)-N-methylpyrrolidine-2-carboxamide 在 三氧化硫吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.5h， 以59%的产率得到(3R,8S,8aS)-8-(tert-butyldimethylsilyloxy)-3-hydroxy-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.