methyl (2R,4S)-4-hydroxy-1-toluenesulfonyl-2-piperidinecarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R,4S)-4-hydroxy-1-toluenesulfonyl-2-piperidinecarboxylate
• 英文别名: methyl (2R,4S)-4-hydroxy-1-(4-methylphenyl)sulfonylpiperidine-2-carboxylate
• 化学式: C₁₄H₁₉NO₅S
• 分子量: 313.375
• InChiKey: OBCJRABBYPUFMP-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 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：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-烯丙基甘氨酸 在 吡啶 、 氯化亚砜 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 methyl (2R,4S)-4-hydroxy-1-toluenesulfonyl-2-piperidinecarboxylate
  参考文献：
  名称：

  Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid DerivedN-Acyliminium Ions

  摘要：

  The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<1127::aid-ejoc1127>3.0.co;2-a

文献信息

• Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid DerivedN-Acyliminium Ions
  作者：Floris P. J. T. Rutjes、Johan J. N. Veerman、Wim J. N. Meester、Henk Hiemstra、Hans E. Schoemaker

  DOI：10.1002/(sici)1099-0690(199905)1999:5<1127::aid-ejoc1127>3.0.co;2-a

  日期：1999.5

  The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.

表征谱图