rel-(2R,3S,4S)-3-ethyl-4-hydroxy-2-piperidinecarboxylic acid | 136294-25-2

• 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: rel-(2R,3S,4S)-3-ethyl-4-hydroxy-2-piperidinecarboxylic acid
• 英文别名: (2R,3S,4S)-3-ethyl-4-hydroxypiperidine-2-carboxylic acid
• CAS: 136294-25-2；136294-26-3
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: JTOKFRJYJFTKPP-DSYKOEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.18
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  69.56
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  acetoxyacetic acid methyl ester 在 盐酸 、 四氯化锡 、 碳酸氢钠 作用下， 反应 20.25h， 生成 rel-(2R,3S,4S)-3-ethyl-4-hydroxy-2-piperidinecarboxylic acid
  参考文献：
  名称：

  Tin tetrachloride-induced π-cyclizations of glycine cation equivalents to substituted pipecolic acid derivatives

  摘要：

  Cationic pi-cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)acetoxyglycine esters induced by tin tetrachloride in dichloromethane are described. Reactions started and quenched with water at -78-degrees-C mainly yield cis-4-hydroxypipecolic esters, whereas reactions quenched after warm-up to room temperature provide trans-4-chloropipecolic esters as major products. A mechanistic scheme is advanced which adequately explains these results. The essentials are a rapid cationic aza-Cope equilibrium of the incipient iminium cation, and participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.

  DOI：

  10.1016/s0040-4020(01)86443-7