4(S)-<(tert-butyldimethylsilyl)oxy>-5(R)-<(phenylseleno)methyl>-2-pyrrolidinone | 142722-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4(S)-<(tert-butyldimethylsilyl)oxy>-5(R)-<(phenylseleno)methyl>-2-pyrrolidinone
• 英文别名: (4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(phenylselanylmethyl)pyrrolidin-2-one
• CAS: 142722-87-0
• 化学式: C₁₇H₂₇NO₂SeSi
• 分子量: 384.452
• InChiKey: ZNUPKHPURSXZSR-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4(S)-<(tert-butyldimethylsilyl)oxy>-5(R)-<(phenylseleno)methyl>-2-pyrrolidinone 在 palladium on activated charcoal 吡啶 、 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 40.92h， 生成 流涎胺
  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：

  4(S)-hydroxy-5(R)-(iodomethyl)-2-pyrrolidinone 在 咪唑 、 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4(S)-<(tert-butyldimethylsilyl)oxy>-5(R)-<(phenylseleno)methyl>-2-pyrrolidinone
  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

文献信息

• Radical routes to indolizidines. Synthesis of (-)-slaframine
  作者：Spencer Knapp、Frank S. Gibson

  DOI：10.1021/jo00044a011

  日期：1992.8

  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.