(1'R)-4-(4-phenylsulfanylbenzenesulfonyl)-1-[1'-benzyloxymethyl-2'-hydroxyethyl]-2-oxopiperazine | 1060662-43-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1'R)-4-(4-phenylsulfanylbenzenesulfonyl)-1-[1'-benzyloxymethyl-2'-hydroxyethyl]-2-oxopiperazine
• 英文别名: 1-[(2R)-1-hydroxy-3-phenylmethoxypropan-2-yl]-4-(4-phenylsulfanylphenyl)sulfonylpiperazin-2-one
• CAS: 1060662-43-2
• 化学式: C₂₆H₂₈N₂O₅S₂
• 分子量: 512.651
• InChiKey: YBCSCUDCMKKNFV-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1'R)-4-(4-nitrobenzenesulfonyl)-1-[1'-benzyloxymethyl-2'-hydroxyethyl]-2-oxopiperazine 、 苯硫酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以60%的产率得到(1'R)-4-(4-phenylsulfanylbenzenesulfonyl)-1-[1'-benzyloxymethyl-2'-hydroxyethyl]-2-oxopiperazine
  参考文献：
  名称：

  New efficient enantioselective synthesis of 2-oxopiperazines: a practical access to chiral 3-substituted 2-oxopiperazines

  摘要：

  The development of efficient and stereoselective methods to produce 1,4-disubstituted-2-oxopiperazine in enantiomerically pure form, from a readily available starting material is crucial. Herein, we report a reduction modification to our previously described synthesis of 1,4-disubstituted-2-oxopiperazine and also two original shortly accessed pathways. These new pathways can be routinely performed on a multigram scale and should rapidly find a place in the preparation of the 3-substituted-2-oxopiperazine diastereomers. Stereoselective alkylation of 1,4-disubstituted-2-oxopiperazine led to the corresponding (3S)-diastereomer or (3R)-diastereomer from the corresponding 2-oxopiperazine enantiomer with the chiral inductor substituted at the N-1 (1*) position, respectively, in good yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.030