(S)-ethyl N-(2-phenylcyclopropanecarbonyl)-4,4-dimethylpyroglutamate | 620151-96-4

• 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: (S)-ethyl N-(2-phenylcyclopropanecarbonyl)-4,4-dimethylpyroglutamate
• 英文别名: ethyl (2S)-4,4-dimethyl-5-oxo-1-(2-phenylcyclopropanecarbonyl)pyrrolidine-2-carboxylate
• CAS: 620151-96-4
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: IRBVLHWUJIVLTJ-NRXISQOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  phenylmagnesium bromide 、 (S)-ethyl N-(2-phenylcyclopropanecarbonyl)-4,4-dimethylpyroglutamate 以 四氢呋喃 为溶剂， 反应 5.0h， 以77%的产率得到1-benzoyl-2-phenylcyclopropane
  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：

  2-苯基环丙烷羰酰氯 、 (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70%的产率得到(S)-ethyl N-(2-phenylcyclopropanecarbonyl)-4,4-dimethylpyroglutamate
  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.