(3S)-3-acetoxy-N-(2-iodo-4,5-methylenedioxybenzyl)-2,5-pyrrolidinedione | 244260-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (3S)-3-acetoxy-N-(2-iodo-4,5-methylenedioxybenzyl)-2,5-pyrrolidinedione
• 英文别名: [(3S)-1-[(6-iodo-1,3-benzodioxol-5-yl)methyl]-2,5-dioxopyrrolidin-3-yl] acetate
• CAS: 244260-64-8
• 化学式: C₁₄H₁₂INO₆
• 分子量: 417.157
• InChiKey: GHWOXHGAWSUFAS-LBPRGKRZSA-N

物化性质

• 熔点：
  127-128 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  555.1±50.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S)-3-acetoxy-N-(2-iodo-4,5-methylenedioxybenzyl)-2,5-pyrrolidinedione 在 咪唑 、 sodium tetrahydroborate 、 硼烷四氢呋喃络合物 、 palladium(III) acetate 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 22.0h， 生成 (1S,10R,10aS)-10-(tert-butoxycarbonylmethyl)-1-triethylsilyloxy-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 、 (3S)-acetoxy-2,5-pyrrolidinedione 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到(3S)-3-acetoxy-N-(2-iodo-4,5-methylenedioxybenzyl)-2,5-pyrrolidinedione
  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