4(S)-hydroxy-5(R)-(iodomethyl)-2-pyrrolidinone | 142722-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4(S)-hydroxy-5(R)-(iodomethyl)-2-pyrrolidinone
• 英文别名: (4S,5R)-4-hydroxy-5-(iodomethyl)pyrrolidin-2-one
• CAS: 142722-82-5
• 化学式: C₅H₈INO₂
• 分子量: 241.029
• InChiKey: LQJFFCWVNLXXIO-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4(S)-hydroxy-5(R)-(iodomethyl)-2-pyrrolidinone 在 palladium on activated charcoal 吡啶 、 咪唑 、 sodium tetrahydroborate 、 sodium azide 、 偶氮二异丁腈 、 四甲基乙二胺 、 dimethyl sulfide borane 、 三(三甲基硅基)硅烷 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 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 、 苯 为溶剂， 反应 45.42h， 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(S)-hydroxy-4-pentenamide 在 三氟甲磺酸三甲基硅酯 、 碘 、 三乙胺 作用下， 生成 4(S)-hydroxy-5(R)-(iodomethyl)-2-pyrrolidinone 、 2-Pyrrolidinone, 4-hydroxy-5-(iodomethyl)-, (4S-cis)-
  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