[(1S,6R,8aS)-6-(oxan-2-yloxy)-3-oxo-2,5,6,7,8,8a-hexahydro-1H-indolizin-1-yl] acetate | 142722-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: [(1S,6R,8aS)-6-(oxan-2-yloxy)-3-oxo-2,5,6,7,8,8a-hexahydro-1H-indolizin-1-yl] acetate
• CAS: 142722-96-1；142793-76-8；142793-77-9；142793-78-0
• 化学式: C₁₅H₂₃NO₅
• 分子量: 297.351
• InChiKey: UMZGVZKAJHXYDP-MHDSIBQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1S,6R,8aS)-6-(oxan-2-yloxy)-3-oxo-2,5,6,7,8,8a-hexahydro-1H-indolizin-1-yl] acetate 在 palladium on activated charcoal 吡啶 、 sodium azide 、 四甲基乙二胺 、 dimethyl sulfide borane 、 氢气 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 生成 (1S,6S,8aS)-1-acetoxy-6-(N-acetylamino)-1,2,3,5,6,7,8,8a-octahydroindolizin
  参考文献：
  名称：

  Radical routes to indolizidines. Synthesis of (-)-slaframine

  摘要：

  The synthesis of (-)-slaframine (5) was executed in 11 steps and 25% overall yield from resolved 3(S)-hydroxy-4-pentenamide (22). Two cyclization reactions were used to form the indolizidine skeleton and also to provide the necessary stereocontrol at C-8a and C-6 of the natural product. "Iodolactamization" of 22 gave selectively the cis-pyrrolidinone 21. Later in the synthesis, a silane-mediated radical cyclization of the phenylseleno lactam 33 gave selectively the 6-alpha-hydroxyindolizidinone 35a, an event predictable from model studies-such as 14c --> 15c. Replacement of hydroxy with azido and reduction of the lactam carbonyl gave "slaframine azide", 38, a stable and easily convertible immediate precursor to 5.

  DOI：

  10.1021/jo00044a011
• 作为产物：
  描述：

  3-iodo-2-(2-tetrahydropyranyloxy)propene 在 吡啶 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 17.25h， 生成 [(1S,6R,8aS)-6-(oxan-2-yloxy)-3-oxo-2,5,6,7,8,8a-hexahydro-1H-indolizin-1-yl] acetate
  参考文献：
  名称：

  Radical routes to indolizidines. Synthesis of (-)-slaframine

  摘要：

  The synthesis of (-)-slaframine (5) was executed in 11 steps and 25% overall yield from resolved 3(S)-hydroxy-4-pentenamide (22). Two cyclization reactions were used to form the indolizidine skeleton and also to provide the necessary stereocontrol at C-8a and C-6 of the natural product. "Iodolactamization" of 22 gave selectively the cis-pyrrolidinone 21. Later in the synthesis, a silane-mediated radical cyclization of the phenylseleno lactam 33 gave selectively the 6-alpha-hydroxyindolizidinone 35a, an event predictable from model studies-such as 14c --> 15c. Replacement of hydroxy with azido and reduction of the lactam carbonyl gave "slaframine azide", 38, a stable and easily convertible immediate precursor to 5.

  DOI：

  10.1021/jo00044a011