rel-(5R,7S,8aS)-7-formyloxy-octahydro-3-oxoindolizine-5-carboxylic acid methyl ester | 135690-83-4

• 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-(5R,7S,8aS)-7-formyloxy-octahydro-3-oxoindolizine-5-carboxylic acid methyl ester
• 英文别名: methyl (5S,7R,8aR)-7-formyloxy-3-oxo-2,5,6,7,8,8a-hexahydro-1H-indolizine-5-carboxylate
• CAS: 135690-83-4；135759-51-2
• 化学式: C₁₁H₁₅NO₅
• 分子量: 241.244
• InChiKey: CATJJXLHYPWYFU-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲酸 、 α-acetoxy-2-oxo-5-(2-propenyl)-pyrrolidineacetic acid methyl ester 反应 17.0h， 以39%的产率得到rel-(5R,7S,8aS)-7-formyloxy-octahydro-3-oxoindolizine-5-carboxylic 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

文献信息

• Synthesis of Chiral Non Racemic Indolizidin-3-ones as Peptidomimetic Scaffold
  作者：Jacques Royer、Delphine Halie、Jo鼠le P屍ard-Viret

  DOI：10.3987/com-06-10891

  日期：——
• Formic acid-induced π-cyclization of glycine cation equivalents to substituted pipecolic acid derivatives
  作者：Peter M Esch、de Boer F Richard、Hiemstra Henk、Ilona M Boska、Speckamp W. Nico

  DOI：10.1016/s0040-4020(01)86444-9

  日期：1991.1

  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.