4-(1-chloroethyl)-1,2-pyrrolidinedicarboxylic acid dimethyl ester | 136294-16-1

• 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: 4-(1-chloroethyl)-1,2-pyrrolidinedicarboxylic acid dimethyl ester
• 英文别名: dimethyl 4-(1-chloroethyl)pyrrolidine-1,2-dicarboxylate
• CAS: 136294-16-1
• 化学式: C₁₀H₁₆ClNO₄
• 分子量: 249.694
• InChiKey: BHLFPGYCSKWXBP-UHFFFAOYSA-N

物化性质

• 沸点：
  320.5±27.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  hydroxyacetic acid dimethyl ester 在 吡啶 、 4-二甲氨基吡啶 、 四氯化锡 、 碳酸氢钠 作用下， 反应 22.0h， 生成 4-(1-chloroethyl)-1,2-pyrrolidinedicarboxylic acid dimethyl ester
  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