ethyl (2S)-4,4-dimethyl-5-oxo-1-(3-phenylprop-2-ynoyl)pyrrolidine-2-carboxylate | 620151-90-8

• 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: ethyl (2S)-4,4-dimethyl-5-oxo-1-(3-phenylprop-2-ynoyl)pyrrolidine-2-carboxylate
• CAS: 620151-90-8
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: YFZGVHUFMKRMRW-AWEZNQCLSA-N

物化性质

• 沸点：
  421.5±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sodium ethanolate 、 ethyl (2S)-4,4-dimethyl-5-oxo-1-(3-phenylprop-2-ynoyl)pyrrolidine-2-carboxylate 以 乙醇 为溶剂， 反应 1.0h， 以79%的产率得到苯丙炔酸乙酯
  参考文献：
  名称：

  Chemoselective Nucleophilic Attack on N-Acyl Derivatives of (S)-Ethyl 4,4-Dimethyl Pyroglutamate (DMPG)

  摘要：

  [GRAPHICS]Heteronucleophiles and C-nucleophiles chemoselectively react with n-acyl (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG) affording esters, amides, and ketones in high yield. The intramolecular process allows the stereoselective formation of beta-hydroxy acids likely by formation and ring opening of the corresponding beta-lactones.

  DOI：

  10.1021/ol034847m
• 作为产物：
  描述：

  phenylpropiolyl chloride 、 (2S)-4,4-二甲基-5-氧代吡咯烷-2-羧酸乙酯 在 正丁基锂 作用下， 以28%的产率得到ethyl (2S)-4,4-dimethyl-5-oxo-1-(3-phenylprop-2-ynoyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Chemoselective Nucleophilic Attack on N-Acyl Derivatives of (S)-Ethyl 4,4-Dimethyl Pyroglutamate (DMPG)

  摘要：

  [GRAPHICS]Heteronucleophiles and C-nucleophiles chemoselectively react with n-acyl (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG) affording esters, amides, and ketones in high yield. The intramolecular process allows the stereoselective formation of beta-hydroxy acids likely by formation and ring opening of the corresponding beta-lactones.

  DOI：

  10.1021/ol034847m

文献信息

• Chemoselective Nucleophilic Attack on <i>N</i>-Acyl Derivatives of (<i>S</i>)-Ethyl 4,4-Dimethyl Pyroglutamate (DMPG)
  作者：Susana Mantecón、Juan J. Vaquero、Julio Alvarez-Builla、María Luz de la Puente、Juan F. Espinosa、Jesús Ezquerra

  DOI：10.1021/ol034847m

  日期：2003.10.1

  [GRAPHICS]Heteronucleophiles and C-nucleophiles chemoselectively react with n-acyl (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG) affording esters, amides, and ketones in high yield. The intramolecular process allows the stereoselective formation of beta-hydroxy acids likely by formation and ring opening of the corresponding beta-lactones.