(4S,5R)-(E)-N-[2-(tert-butoxycarbonylethenyl)-4,5-methylenedioxybenzyl]-4-triethylsilyloxy-5-phenylselenylpyrrolidin-2-one | 500213-41-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4S,5R)-(E)-N-[2-(tert-butoxycarbonylethenyl)-4,5-methylenedioxybenzyl]-4-triethylsilyloxy-5-phenylselenylpyrrolidin-2-one
• 英文别名: tert-butyl (E)-3-[6-[[(2R,3S)-5-oxo-2-phenylselanyl-3-triethylsilyloxypyrrolidin-1-yl]methyl]-1,3-benzodioxol-5-yl]prop-2-enoate
• CAS: 500213-41-2
• 化学式: C₃₁H₄₁NO₆SeSi
• 分子量: 630.715
• InChiKey: UKVAZWNWTRTYTB-PZJHYLMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5R)-(E)-N-[2-(tert-butoxycarbonylethenyl)-4,5-methylenedioxybenzyl]-4-triethylsilyloxy-5-phenylselenylpyrrolidin-2-one 在 吡啶 、 盐酸 、 正丁基锂 、 硼烷四氢呋喃络合物 、 偶氮二异丁腈 、 三正丁基氢锡 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 11.59h， 生成 (1S,10R,10aR,2'S)-10-(2'-acetoxy-4'-trimethylsilyl-3'-butynyl)-1-hydroxy-7,8-methylenedioxy-1,2,3,5,10,10a-hexahydrobenz[f]indolizidine
  参考文献：
  名称：

  Synthesis of Optically Active 2-Acetoxy-3-alkylidene-a-lycoranes for a Synthetic Approach toward (+)-Lycorine by Radical Reaction

  摘要：

  A radical-mediated synthesis of optically active 2alpha- and 2beta-trimethylsilylmethyene-alpha-lycoranes (3,4), which are key intermediates for synthesis of (+)- lycorine (2), is described. Thus, both B and C rings in lycorine (2) were constructed by 6-exo mode radical cyclization. The former ring formation was performed in diastereoselective manner by radical cyclization via alpha-acylamino radical of (4S,5R)-4-acetoxy-N-(2-methoxy-, benzyloxy-, and tert-butoxy-carbonylethenyl-4,5-methylenedioxybenzyl)- or (4S,5R)-N-(2-tert-butoxycarbonylethenyl-4,5-methylenedioxybenzyl)-4-triethyisilyloxy-5-phenyl- selenyl-2-pyrrolidinones (10-12 or 19). The latter ring formation was accomplished by the reaction of (1S,10R,10aR,2'S)- and (1S,10R,10aR,2'R)-10-(2'-acetoxy-4'-trimethylsilyl-3'-butynyl)-1-imidazolylthiocarbonyloxy-7,8-methylenedioxy- 1,2,3,5, 10, 10a-hexahydrobenz[f]indolizidines (28).

  DOI：

  10.3987/com-02-9610
• 作为产物：
  描述：

  (6-碘苯并[1,3]二氧杂环戊烯-5-基)甲醇 在 咪唑 、 sodium tetrahydroborate 、 palladium(III) acetate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 (4S,5R)-(E)-N-[2-(tert-butoxycarbonylethenyl)-4,5-methylenedioxybenzyl]-4-triethylsilyloxy-5-phenylselenylpyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of Optically Active 2-Acetoxy-3-alkylidene-a-lycoranes for a Synthetic Approach toward (+)-Lycorine by Radical Reaction

  摘要：

  A radical-mediated synthesis of optically active 2alpha- and 2beta-trimethylsilylmethyene-alpha-lycoranes (3,4), which are key intermediates for synthesis of (+)- lycorine (2), is described. Thus, both B and C rings in lycorine (2) were constructed by 6-exo mode radical cyclization. The former ring formation was performed in diastereoselective manner by radical cyclization via alpha-acylamino radical of (4S,5R)-4-acetoxy-N-(2-methoxy-, benzyloxy-, and tert-butoxy-carbonylethenyl-4,5-methylenedioxybenzyl)- or (4S,5R)-N-(2-tert-butoxycarbonylethenyl-4,5-methylenedioxybenzyl)-4-triethyisilyloxy-5-phenyl- selenyl-2-pyrrolidinones (10-12 or 19). The latter ring formation was accomplished by the reaction of (1S,10R,10aR,2'S)- and (1S,10R,10aR,2'R)-10-(2'-acetoxy-4'-trimethylsilyl-3'-butynyl)-1-imidazolylthiocarbonyloxy-7,8-methylenedioxy- 1,2,3,5, 10, 10a-hexahydrobenz[f]indolizidines (28).

  DOI：

  10.3987/com-02-9610

文献信息

• Synthesis of Optically Active 2-Acetoxy-3-alkylidene-a-lycoranes for a Synthetic Approach toward (+)-Lycorine by Radical Reaction
  作者：Miyuki Ishizaki、Yuichiro Kai、Osamu Hoshino

  DOI：10.3987/com-02-9610

  日期：——

  A radical-mediated synthesis of optically active 2alpha- and 2beta-trimethylsilylmethyene-alpha-lycoranes (3,4), which are key intermediates for synthesis of (+)- lycorine (2), is described. Thus, both B and C rings in lycorine (2) were constructed by 6-exo mode radical cyclization. The former ring formation was performed in diastereoselective manner by radical cyclization via alpha-acylamino radical of (4S,5R)-4-acetoxy-N-(2-methoxy-, benzyloxy-, and tert-butoxy-carbonylethenyl-4,5-methylenedioxybenzyl)- or (4S,5R)-N-(2-tert-butoxycarbonylethenyl-4,5-methylenedioxybenzyl)-4-triethyisilyloxy-5-phenyl- selenyl-2-pyrrolidinones (10-12 or 19). The latter ring formation was accomplished by the reaction of (1S,10R,10aR,2'S)- and (1S,10R,10aR,2'R)-10-(2'-acetoxy-4'-trimethylsilyl-3'-butynyl)-1-imidazolylthiocarbonyloxy-7,8-methylenedioxy- 1,2,3,5, 10, 10a-hexahydrobenz[f]indolizidines (28).