(2R,3S,6S)-2-Hydroxymethyl-3-methyl-4-oxo-6-phenyl-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester | 209160-21-4

• 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: (2R,3S,6S)-2-Hydroxymethyl-3-methyl-4-oxo-6-phenyl-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester
• 英文别名: 2,2,2-trichloroethyl (2R,3S,6S)-2-(hydroxymethyl)-3-methyl-4-oxo-6-phenylpiperidine-1-carboxylate
• CAS: 209160-21-4
• 化学式: C₁₆H₁₈Cl₃NO₄
• 分子量: 394.682
• InChiKey: LFENQRPNQASGJU-DRZSPHRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,6S)-2-Hydroxymethyl-3-methyl-4-oxo-6-phenyl-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester 在 jones reagent 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 2.25h， 生成 (2R,3S,6S)-3-Methyl-4-oxo-6-phenyl-piperidine-1,2-dicarboxylic acid 2-methyl ester 1-(2,2,2-trichloro-ethyl) ester
  参考文献：
  名称：

  Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives

  摘要：

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.

  DOI：

  10.1021/jo9722414
• 作为产物：
  描述：

  (2S*,3R*,6R*)-2-(hydroxymethyl)-3-methyl-6-phenyl-4-piperidone 在 吡啶 、 咪唑 、 盐酸 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 (2R,3S,6S)-2-Hydroxymethyl-3-methyl-4-oxo-6-phenyl-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives

  摘要：

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.

  DOI：

  10.1021/jo9722414

文献信息

• Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives
  作者：José Barluenga、Fernando Aznar、Carlos Valdés、Cristina Ribas

  DOI：10.1021/jo9722414

  日期：1998.6.1

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.