ethyl 2-phenyl(pyrrolidin-2-ylidene)ethanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-phenyl(pyrrolidin-2-ylidene)ethanoate
• 英文别名: ethyl (2Z)-2-phenyl-2-pyrrolidin-2-ylideneacetate
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: IOEXPJOCXAPYFO-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯丁腈 、 α-溴苯乙酸乙酯 在 甲烷磺酸 、 锌 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以71%的产率得到ethyl 2-phenyl(pyrrolidin-2-ylidene)ethanoate
  参考文献：
  名称：

  Chemoselective Intramolecular Alkylation of the Blaise Reaction Intermediates: Tandem One-Pot Synthesis of exo-Cyclic Enaminoesters and Their Applications toward the Synthesis of N-Heterocyclic Compounds

  摘要：

  The intramolecular alkylative reactivity and N/C selectivity of the various Blaise reaction intermediates, which are formed from the reaction of the Reformatsky reagents with omega-chloroalkyl nitriles, did not reach the synthetic potential as an entry to exo-cyclic enaminoesters. To circumvent this issue, various additives were investigated, among which the addition of NaHMDS dramatically enhanced the reactivity and N/C selectivity. This modification provided a highly efficient route for the synthesis of various N-fused heterocyclic compounds, as it requires only two steps from nitriles.

  DOI：

  10.1021/jo201964a

文献信息

• Chemoselective Intramolecular Alkylation of the Blaise Reaction Intermediates: Tandem One-Pot Synthesis of <i>exo</i>-Cyclic Enaminoesters and Their Applications toward the Synthesis of <i>N</i>-Heterocyclic Compounds
  作者：Ju Hyun Kim、Hyunik Shin、Sang-gi Lee

  DOI：10.1021/jo201964a

  日期：2012.2.3

  The intramolecular alkylative reactivity and N/C selectivity of the various Blaise reaction intermediates, which are formed from the reaction of the Reformatsky reagents with omega-chloroalkyl nitriles, did not reach the synthetic potential as an entry to exo-cyclic enaminoesters. To circumvent this issue, various additives were investigated, among which the addition of NaHMDS dramatically enhanced the reactivity and N/C selectivity. This modification provided a highly efficient route for the synthesis of various N-fused heterocyclic compounds, as it requires only two steps from nitriles.