4-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]-2,3-dihydroxy-2-methylbutanoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]-2,3-dihydroxy-2-methylbutanoic acid
• 英文别名: (2R,3R)-4-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-2,3-dihydroxy-2-methylbutanoic acid
• 化学式: C₁₄H₁₇NO₇
• 分子量: 311.291
• InChiKey: ZHWXAOZKNCMTES-UOLJMSNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  147
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 4-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]-2,3-dihydroxy-2-methylbutanoic acid
  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.