acetoxyacetic acid methyl ester | 135690-89-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: acetoxyacetic acid methyl ester
• 英文别名: methyl 2-acetyloxy-2-[but-3-enyl(methoxycarbonyl)amino]acetate
• CAS: 135690-89-0
• 化学式: C₁₁H₁₇NO₆
• 分子量: 259.259
• InChiKey: MZKUCROFULFHNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  acetoxyacetic acid methyl ester 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 cis-4-formyloxy-d-1,2-piperidinedicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Formic acid-induced π-cyclization of glycine cation equivalents to substituted pipecolic acid derivatives

  摘要：

  Formic acid-mediated cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)-acetoxyglycine esters are described. The major reaction products are 4-formyloxypipecolic acid derivatives, formed with low stereoselectivity at C-4. The several subtle features of the cyclization process are satisfactorily explained by a mechanism involving (1) a rapid cationic aza-Cope rearrangement of the incipient iminium ion and (2) participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.

  DOI：

  10.1016/s0040-4020(01)86444-9
• 作为产物：
  描述：

  methyl N-(3-butenyl)carbamate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 苯 为溶剂， 生成 acetoxyacetic acid methyl ester
  参考文献：
  名称：

  Formic acid-induced π-cyclization of glycine cation equivalents to substituted pipecolic acid derivatives

  摘要：

  Formic acid-mediated cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)-acetoxyglycine esters are described. The major reaction products are 4-formyloxypipecolic acid derivatives, formed with low stereoselectivity at C-4. The several subtle features of the cyclization process are satisfactorily explained by a mechanism involving (1) a rapid cationic aza-Cope rearrangement of the incipient iminium ion and (2) participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.

  DOI：

  10.1016/s0040-4020(01)86444-9