ethyl (4S,5R)-[4-benzyloxy-1-(4-methoxybenzyl)-2-oxopyrrolidin-5-yl]acetate | 812644-93-2

• 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: ethyl (4S,5R)-[4-benzyloxy-1-(4-methoxybenzyl)-2-oxopyrrolidin-5-yl]acetate
• 英文别名: ethyl 2-[(2R,3S)-1-[(4-methoxyphenyl)methyl]-5-oxo-3-phenylmethoxypyrrolidin-2-yl]acetate
• CAS: 812644-93-2
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: KZSVEWLYTPHZMJ-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (4S,5R)-[4-benzyloxy-1-(4-methoxybenzyl)-2-oxopyrrolidin-5-yl]acetate 在 palladium on activated charcoal lithium hydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 221.0h， 生成 (4S,5R)-2-[4-hydroxy-1-(4-methoxybenzyl)-2-oxopyrrolidin-5-yl]acetic acid
  参考文献：
  名称：

  A novel approach to the Geissman–Waiss lactone and a key intermediate in the synthesis of pyrrolidine trans-lactones

  摘要：

  Based on the highly regio- and diastereoselective reductive-ethoxycarbonylmethylation of protected (S)-malimide 4, a new approach to the Geissman-Waiss lactone 1 and a key intermediate 3 for the synthesis of pyrrolidine trans-lactones (e.g., 2) is described. The synthesis features a one-step and a two-step chemoselective reduction of an amide carbonyl in the presence of an ester group as the key steps. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.020
• 作为产物：
  描述：

  [(S)-3-Benzyloxy-2-hydroxy-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-2-yl]-acetic acid ethyl ester 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到ethyl (4S,5R)-[4-benzyloxy-1-(4-methoxybenzyl)-2-oxopyrrolidin-5-yl]acetate
  参考文献：
  名称：

  A novel approach to the Geissman–Waiss lactone and a key intermediate in the synthesis of pyrrolidine trans-lactones

  摘要：

  Based on the highly regio- and diastereoselective reductive-ethoxycarbonylmethylation of protected (S)-malimide 4, a new approach to the Geissman-Waiss lactone 1 and a key intermediate 3 for the synthesis of pyrrolidine trans-lactones (e.g., 2) is described. The synthesis features a one-step and a two-step chemoselective reduction of an amide carbonyl in the presence of an ester group as the key steps. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.020