(3S,6S)-6-Benzyl-2,5-dioxo-piperidine-3-carboxylic acid methyl ester | 135941-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3S,6S)-6-Benzyl-2,5-dioxo-piperidine-3-carboxylic acid methyl ester
• 英文别名: methyl (3S,6S)-6-benzyl-2,5-dioxopiperidine-3-carboxylate
• CAS: 135941-68-3
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: KUOYURMPTIMQEY-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,6S)-6-Benzyl-2,5-dioxo-piperidine-3-carboxylic acid methyl ester 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 10.0h， 生成 (S)-3,6-Dibenzyl-2,5-dioxo-piperidine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of cyclic ketomethylene dipeptide derivatives

  摘要：

  Methyl 6-aralkyl-2,5-diketopiperidine-3-carboxylates derived from L-Phe and L-Trp, and their 3-substituted analogues in which the 3-substituent is the side chain of Phe, Asp and Ala have been synthesized. Cycle[Trp-psi(COCH2)Gly] and cycle[Phe-psi(COCH2)-xi-Phe] have been also prepared.

  DOI：

  10.1016/s0040-4020(01)88534-3
• 作为产物：
  描述：

  dimethyl 2-[(3S)-2-oxo-4-phenyl-3-(phenylmethoxycarbonylamino)butyl]propanedioate 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、172.37 kPa 条件下， 反应 48.0h， 生成 (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

文献信息

• Synthesis of methyl 6-aralkl-2,5-diketopiperidine-3-carboxylates as synthons of conformationally constrained pseudopeptides
  作者：Isabel Gómez-Monterrey、Ma.José Domínguez、Rosario González-Muñiz、Juan R. Harto、Ma.Teresa García-López

  DOI：10.1016/0040-4039(91)80834-s

  日期：1991.7

  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.
• Synthesis of cyclic ketomethylene dipeptide derivatives
  作者：M.J. Domínguez、R. González-Muñiz、M.T. García-López

  DOI：10.1016/s0040-4020(01)88534-3

  日期：1992.3

  Methyl 6-aralkyl-2,5-diketopiperidine-3-carboxylates derived from L-Phe and L-Trp, and their 3-substituted analogues in which the 3-substituent is the side chain of Phe, Asp and Ala have been synthesized. Cycle[Trp-psi(COCH2)Gly] and cycle[Phe-psi(COCH2)-xi-Phe] have been also prepared.