(S)-ethyl 4,4-dimethyl-N-propionylpyroglutamate | 189098-08-6

• 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 4,4-dimethyl-N-propionylpyroglutamate
• 英文别名: ethyl (2S)-4,4-dimethyl-5-oxo-1-propanoylpyrrolidine-2-carboxylate
• CAS: 189098-08-6
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: YOJKIAFIBSCJBK-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  壬醛 、 (S)-ethyl 4,4-dimethyl-N-propionylpyroglutamate 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(2S)-ethyl N-[2R,3S-(3-hydroxy-2-methylundecanoyl)]-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
• 作为产物：
  描述：

  BOC-L-焦谷氨酸乙酯 在 正丁基锂 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-ethyl 4,4-dimethyl-N-propionylpyroglutamate
  参考文献：
  名称：

  (S)-Ethyl 4,4-dimethyl pyroglutamate as a new ‘quat’ chiral auxiliary in aldol condensations

  摘要：

  Enolates I, derived from the N-propionyl derivative of the 'quat' chiral auxiliary (S)-ethyl 4,4-dimethyl pyroglutamate 4 undergo highly stereoselective aldol reactions, which upon hydrolysis and removal of the chiral auxiliary yields the (2R,3R)-3-hydroxy-2-methylpropionic acid 9 in homochiral form. Remarkably, the stereogenic center of 4 was not affected during all the chemical transformations and it could be regenerated after the process in 70% yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00028-1

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.
• (S)-Ethyl 4,4-dimethyl pyroglutamate as a new ‘quat’ chiral auxiliary in aldol condensations
  作者：Jesús Ezquerra、Almudena Rubio、Justina Martín、JoséLuis García Navío

  DOI：10.1016/s0957-4166(97)00028-1

  日期：1997.3

  Enolates I, derived from the N-propionyl derivative of the 'quat' chiral auxiliary (S)-ethyl 4,4-dimethyl pyroglutamate 4 undergo highly stereoselective aldol reactions, which upon hydrolysis and removal of the chiral auxiliary yields the (2R,3R)-3-hydroxy-2-methylpropionic acid 9 in homochiral form. Remarkably, the stereogenic center of 4 was not affected during all the chemical transformations and it could be regenerated after the process in 70% yield. (C) 1997 Elsevier Science Ltd.