methyl (2S)-N-(phenylacetyl)pyroglutamate | 72719-13-2

• 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: methyl (2S)-N-(phenylacetyl)pyroglutamate
• 英文别名: methyl (2S)-5-oxo-1-(2-phenylacetyl)pyrrolidine-2-carboxylate
• CAS: 72719-13-2
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: ODDCKAZQWSFWLA-NSHDSACASA-N

物化性质

• 沸点：
  424.6±45.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 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：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙酸 、 L-焦谷氨酸甲酯 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 以39%的产率得到methyl (2S)-N-(phenylacetyl)pyroglutamate
  参考文献：
  名称：

  Straightforward and Facile Approach Toward the N-Derivatization of Pyroglutamates Through Mitsunobu Reaction: Synthesis of N-Alkyl/N-Acyl Pyroglutamates

  摘要：

  Pyroglutamates have been acknowledged as useful chiral synthons for the synthesis of many bioactive natural products, ACE inhibitors, and conformationally constrained peptides. Though the reactivity differences between two differential carbonyl groups have been well exploited, there is still a dearth of publications on the N-alkylation/acylation of native pyroglutamate as such, due to the relatively low reactivity of NH of pyroglutamates. In the present communication, we report for the first time a simple and efficient methodology for the N-alkylation/acylation of pyroglutamate via Mitsunobu reaction.

  DOI：

  10.1080/00397911.2010.519844

文献信息

• Straightforward and Facile Approach Toward the N-Derivatization of Pyroglutamates Through Mitsunobu Reaction: Synthesis of N-Alkyl/N-Acyl Pyroglutamates
  作者：Sharad Kumar Panday、Jagdish Prasad、Manoher Bhushan Pathak

  DOI：10.1080/00397911.2010.519844

  日期：2011.12.15

  Pyroglutamates have been acknowledged as useful chiral synthons for the synthesis of many bioactive natural products, ACE inhibitors, and conformationally constrained peptides. Though the reactivity differences between two differential carbonyl groups have been well exploited, there is still a dearth of publications on the N-alkylation/acylation of native pyroglutamate as such, due to the relatively low reactivity of NH of pyroglutamates. In the present communication, we report for the first time a simple and efficient methodology for the N-alkylation/acylation of pyroglutamate via Mitsunobu reaction.