2-Pyrrolidinone, 3,4-dihydroxy-3-methyl-, (3R,4R)-rel- | 1354355-25-1

• 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: 2-Pyrrolidinone, 3,4-dihydroxy-3-methyl-, (3R,4R)-rel-
• 英文别名: (3R,4R)-3,4-dihydroxy-3-methylpyrrolidin-2-one
• CAS: 1354355-25-1
• 化学式: C₅H₉NO₃
• 分子量: 131.131
• InChiKey: TWPXBSBMIBIYCM-NQXXGFSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2R,3R)-4-[(E)-3-(3,4-Dihydroxy-phenyl)-acryloylamino]-2,3-dihydroxy-2-methyl-butyric acid ethyl ester 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 2-Pyrrolidinone, 3,4-dihydroxy-3-methyl-, (3R,4R)-rel- 、 (2R,3R)-4-amino-2,3-dihydroxy-2-methylbutanoic acid 、 TRANS-咖啡酸
  参考文献：
  名称：

  First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers

  摘要：

  The synthesis of potassium aeshynomate and its non-natural stereomers was achieved using the Sharpless catalytic asymmetric dihydroxylation of (Z) or (E) vinylogous glycine as the key step. The resulting gamma-amino alpha, beta-dihydroxyester stereomer was deprotected and coupled with the caffeic acid to afford stereoselectively potassium aeshynomate or its stereomers. A detailed study of the NMR data of the different stereomers is reported that corrects the literature data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.051

文献信息

• First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers
  作者：Stéphanie Claudel、Tomasz Krzysztof Olszewski、Pierre Mutzenardt、Christie Aroulanda、Philippe Coutrot、Claude Grison

  DOI：10.1016/j.tet.2005.11.051

  日期：2006.2

  The synthesis of potassium aeshynomate and its non-natural stereomers was achieved using the Sharpless catalytic asymmetric dihydroxylation of (Z) or (E) vinylogous glycine as the key step. The resulting gamma-amino alpha, beta-dihydroxyester stereomer was deprotected and coupled with the caffeic acid to afford stereoselectively potassium aeshynomate or its stereomers. A detailed study of the NMR data of the different stereomers is reported that corrects the literature data. (c) 2005 Elsevier Ltd. All rights reserved.