ethyl 2-(pyrrolidin-2-ylidene)propanoate | 1356393-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: ethyl 2-(pyrrolidin-2-ylidene)propanoate
• 英文别名: ethyl (2E)-2-pyrrolidin-2-ylidenepropanoate
• CAS: 1356393-51-5
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: PUMWPTSGQWHFOR-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-(pyrrolidin-2-ylidene)propanoate 、 硼酸 以95%的产率得到
  参考文献：
  名称：

  BACOS, D.;CELERIER, J. -P.;LHOMMET, G., TETRAHEDRON LETT., 28,(1987) N 21, 2353-2354

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯丁腈 、 2-溴丙酸乙酯 在 甲烷磺酸 、 锌 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以5%的产率得到1-甲基-2-氧代环戊烷-1-羧酸乙酯
  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.
• BACOS, D.;CELERIER, J. -P.;LHOMMET, G., TETRAHEDRON LETT., 28,(1987) N 21, 2353-2354
  作者：BACOS, D.、CELERIER, J. -P.、LHOMMET, G.

  DOI：——

  日期：——