t-butyl 4-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]-2,3-dihydroxy-2-methylbutanoate | 881206-15-1

• 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: t-butyl 4-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]-2,3-dihydroxy-2-methylbutanoate
• 英文别名: (2R,3R)-tert-butyl 4-((E)-3-(3,4-dihydroxyphenyl)acrylamido)-2,3-dihydroxy-2-methylbutanoate；tert-butyl (2R,3R)-4-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-2,3-dihydroxy-2-methylbutanoate
• CAS: 881206-15-1
• 化学式: C₁₈H₂₅NO₇
• 分子量: 367.399
• InChiKey: HLWFBTNAAKXTCB-IUCDDXOCSA-N

物化性质

• 熔点：
  99-100 °C
• 沸点：
  637.3±55.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  t-butyl 4-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]-2,3-dihydroxy-2-methylbutanoate 在 三氟乙酸 作用下， 反应 0.5h， 以98%的产率得到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
• 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 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 t-butyl 4-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]amino]-2,3-dihydroxy-2-methylbutanoate
  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

• Total Synthesis of Enantiopure Potassium Aeshynomate
  作者：Stergios R. Rizos、John G. Stefanakis、Stefanos S. Kotoulas、Alexandros E. Koumbis

  DOI：10.1021/jo5011735

  日期：2014.7.18

  Potassium aeshynomate (1) is the leaf-opening factor of the nyctinastic plant Aeshynomene indica L. In this article a convenient and efficient strategy for the total synthesis of enantiomerically pure 1 is described, starting from the L-arabinose derived chiron ent-6. The realized synthetic scheme involves a postcoupling oxidation approach and securely determines the absolute configuration of the targeted natural product, which remained unknown until now.
• 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.