2-((S)-3-Benzyloxycarbonylamino-2-oxo-4-phenyl-butyl)-malonic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester | 135941-66-1

• 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: 2-((S)-3-Benzyloxycarbonylamino-2-oxo-4-phenyl-butyl)-malonic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester
• 英文别名: 1-O-(2,5-dioxopyrrolidin-1-yl) 3-O-methyl 2-[(3S)-2-oxo-4-phenyl-3-(phenylmethoxycarbonylamino)butyl]propanedioate
• CAS: 135941-66-1
• 化学式: C₂₆H₂₆N₂O₉
• 分子量: 510.5
• InChiKey: BJXFMHSTKRLFDJ-ANYOKISRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  145.38
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-((S)-3-Benzyloxycarbonylamino-2-oxo-4-phenyl-butyl)-malonic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以60%的产率得到(3S,6S)-6-Benzyl-2,5-dioxo-piperidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of methyl 6-aralkl-2,5-diketopiperidine-3-carboxylates as synthons of conformationally constrained pseudopeptides

  摘要：

  Catalytic hydrogenation of the 4-ketoesters 1a,b or 2a,b and their 5R-enantiomers, obtained from the corresponding Z-L- and Z-D-amino acid halomethyl ketones, directly leads to the methyl 6-aralkyl-2,5-diketopiperidine-3-carboxylates 3a,b and 4a,b and their 6R-enantiomers with high or moderate stereoselectivity at C-3.

  DOI：

  10.1016/0040-4039(91)80834-s
• 作为产物：
  描述：

  dimethyl 2-[(3S)-2-oxo-4-phenyl-3-(phenylmethoxycarbonylamino)butyl]propanedioate 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 生成 2-((S)-3-Benzyloxycarbonylamino-2-oxo-4-phenyl-butyl)-malonic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester
  参考文献：
  名称：

  Synthesis of methyl 6-aralkl-2,5-diketopiperidine-3-carboxylates as synthons of conformationally constrained pseudopeptides

  摘要：

  Catalytic hydrogenation of the 4-ketoesters 1a,b or 2a,b and their 5R-enantiomers, obtained from the corresponding Z-L- and Z-D-amino acid halomethyl ketones, directly leads to the methyl 6-aralkyl-2,5-diketopiperidine-3-carboxylates 3a,b and 4a,b and their 6R-enantiomers with high or moderate stereoselectivity at C-3.

  DOI：

  10.1016/0040-4039(91)80834-s