Ethyl 2-(piperidin-2-ylidene)propanoate | 96333-47-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: Ethyl 2-(piperidin-2-ylidene)propanoate
• 英文别名: ethyl 2-piperidin-2-ylidenepropanoate
• CAS: 96333-47-0；113236-62-7
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: UELYEMHELSZOKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  283.0±29.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(piperidin-2-ylidene)propanoate 在 硼酸 作用下， 反应 1.0h， 以65%的产率得到2-乙基-3,4,5,6-四氢吡啶
  参考文献：
  名称：

  Delbecq, Philippe; Bacos, Daniel; Celerier, Jean Pierre, Canadian Journal of Chemistry, 1991, vol. 69, # 8, p. 1201 - 1206

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氯戊腈 、 2-溴丙酸乙酯 在 甲烷磺酸 、 锌 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以67%的产率得到Ethyl 2-(piperidin-2-ylidene)propanoate
  参考文献：
  名称：

  Tandem Transformations of Nitriles into N-Heterocyclic Compounds by Electrophilic Trapping of Blaise Reaction Intermediates

  摘要：

  Tandem transformations of nitriles into various N-heterocycles have been accomplished through the reaction of electrophiles with Blaise reaction intermediates formed in situ. The reaction of the Blaise reaction intermediates with propiolates gives 2-pyridones through consecutive C- and N-nucleophilic reactions. The tandem reactions of the Blaise reaction intermediate with 1,3-enynes proceed through C-nucleophilic addition followed by an electrocyclization-aromatization cascade to give pyridines. Exocyclic enamino esters can be prepared by transformations of omega-chloroalkyl nitriles through chemoselective intramolecular alkylation of the Blaise reaction intermediate. Palladium-catalyzed intramolecular arylations or copper-catalyzed intermolecular cross-coupling reactions of the Blaise reaction intermediate give a range of indole derivatives. Combinations of tandem alkylations and palladium-catalyzed couplings of the Blaise reaction intermediates of omega-chloroalkyl nitriles give N-fused indoles.

  DOI：

  10.1055/s-0031-1290814

文献信息

• Cyclic β-enaminoesters decarboxylation with boric acid: A convenient synthesis of cyclic imines
  作者：Daniel Bacos、Jean-Pierre Celerier、Gérard Lhommet

  DOI：10.1016/s0040-4039(00)96122-7

  日期：——
• Tandem Transformations of Nitriles into N-Heterocyclic Compounds by Electrophilic Trapping of Blaise Reaction Intermediates
  作者：Hyunik Shin、Sang-gi Lee、Ju Kim、Yu Chun

  DOI：10.1055/s-0031-1290814

  日期：2012.6

  Tandem transformations of nitriles into various N-heterocycles have been accomplished through the reaction of electrophiles with Blaise reaction intermediates formed in situ. The reaction of the Blaise reaction intermediates with propiolates gives 2-pyridones through consecutive C- and N-nucleophilic reactions. The tandem reactions of the Blaise reaction intermediate with 1,3-enynes proceed through C-nucleophilic addition followed by an electrocyclization-aromatization cascade to give pyridines. Exocyclic enamino esters can be prepared by transformations of omega-chloroalkyl nitriles through chemoselective intramolecular alkylation of the Blaise reaction intermediate. Palladium-catalyzed intramolecular arylations or copper-catalyzed intermolecular cross-coupling reactions of the Blaise reaction intermediate give a range of indole derivatives. Combinations of tandem alkylations and palladium-catalyzed couplings of the Blaise reaction intermediates of omega-chloroalkyl nitriles give N-fused indoles.
• Delbecq, Philippe; Bacos, Daniel; Celerier, Jean Pierre, Canadian Journal of Chemistry, 1991, vol. 69, # 8, p. 1201 - 1206
  作者：Delbecq, Philippe、Bacos, Daniel、Celerier, Jean Pierre、Lhommet, Gerard

  DOI：——

  日期：——