1-(Carbethoxymethyl)-2-cyano-1,4,5,6-tetrahydropyridine | 132353-44-7

• 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: 1-(Carbethoxymethyl)-2-cyano-1,4,5,6-tetrahydropyridine
• 英文别名: ethyl 2-(6-cyano-3,4-dihydro-2H-pyridin-1-yl)acetate
• CAS: 132353-44-7
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: YYEQLTGEOFWERD-UHFFFAOYSA-N

物化性质

• 沸点：
  318.5±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴戊腈 在 三氟化硼乙醚 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 25.0h， 生成 1-(Carbethoxymethyl)-2-cyano-1,4,5,6-tetrahydropyridine
  参考文献：
  名称：

  Cycloadditions. 50. Multipath reactions between intramolecularly formed oxazolium salts and nucleophiles

  摘要：

  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.

  DOI：

  10.1021/jo00037a023

文献信息

• 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
• HASSNER, ALFRED;FISCHER, BILHA, TETRAHEDRON LETT., 31,(1990) N9, C. 7213-7214
  作者：HASSNER, ALFRED、FISCHER, BILHA

  DOI：——

  日期：——
• 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.