2-Methyl-3-carbethoxy-5,6,7,8-tetrahydroindolizine | 132353-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-Methyl-3-carbethoxy-5,6,7,8-tetrahydroindolizine
• 英文别名: Ethyl 2-methyl-5,6,7,8-tetrahydroindolizine-3-carboxylate
• CAS: 132353-45-8
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: NARPNWAMGTYSCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4'-Bromobutyl)-5-ethoxyoxazole 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium iodide 作用下， 以 乙腈 为溶剂， 生成 2-Methyl-3-carbethoxy-5,6,7,8-tetrahydroindolizine
  参考文献：
  名称：

  Intramolecular formation of oxazolium salts and their reaction with N- and C-nucleophiles.

  摘要：

  DOI：

  10.1016/s0040-4039(00)97282-4

文献信息

• Cycloadditions. 50. Multipath reactions between intramolecularly formed oxazolium salts and nucleophiles
  作者：Alfred Hassner、Bilha Fischer

  DOI：10.1021/jo00037a023

  日期：1992.5

  Reaction of 2-(4'-bromobutyl)-5-ethoxyoxazole (1) with nucleophiles led either to S(N)2 substitution products or to products with a piperidine skeleton. The latter were shown to arise from an intramolecular ring closure to an oxazolium salt 7, which was faster in the presence of a catalytic amount of NaI and in a polar solvent and for which NMR evidence is presented. The further transformation of 7 to 3-6 apparently involves addition of nucleophiles to 7 to produce 4-oxazoline 8 which opens to azomethine ylide 9. Neutralization of the latter occurred either via a proton shift, an alkyl shift, or via trapping by a dipolarophile (electron poor or electron rich). FMO calculations explain the preferred regiochemistry observed during trapping of ylide 9b.
• Intramolecular formation of oxazolium salts and their reaction with N- and C-nucleophiles.
  作者：Alfred Hassner、Bilha Fischer

  DOI：10.1016/s0040-4039(00)97282-4

  日期：1990.1