(4S,5S)-1-(4-methoxybenzyl)-4-(benzyloxy)-5-methyl-2-pyrrolidinone | 1197026-71-3

• 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: (4S,5S)-1-(4-methoxybenzyl)-4-(benzyloxy)-5-methyl-2-pyrrolidinone
• 英文别名: (4S,5S)-1-[(4-methoxyphenyl)methyl]-5-methyl-4-phenylmethoxypyrrolidin-2-one
• CAS: 1197026-71-3
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: POMXGOMPDXJRGK-KXBFYZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4S)-1-[(4-methoxyphenyl)methyl]-5-methylidene-4-phenylmethoxypyrrolidin-2-one 在 palladium 10% on activated carbon 、 ammonium acetate 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以89%的产率得到(4S,5S)-1-(4-methoxybenzyl)-4-(benzyloxy)-5-methyl-2-pyrrolidinone
  参考文献：
  名称：

  A versatile approach to cis-5-substituted 4-hydroxy-2-pyrrolidinones: asymmetric synthesis of angiogenesis inhibitor streptopyrrolidine

  摘要：

  A concise, flexible, and highly diastereoselective approach to cis-5-alkyl-4-hydroxy-2-pyrrolidinones 1 is described. The key step is an ammonium acetate-assisted catalytic hydrogenation of the enamides 9, derived in two steps from malimides 6a,b as we have described previously. The method was applied to the asymmetric synthesis of streptopyrrolidine 5, a natural product, which exhibited significant anti-angiogenesis activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.018