methyl (E)-3-[2-(4-hydroxy-3,5-dimethoxyphenyl)-7-hydroxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]propen-2-enoate | 1316855-24-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: methyl (E)-3-[2-(4-hydroxy-3,5-dimethoxyphenyl)-7-hydroxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]propen-2-enoate
• 英文别名: methyl 7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-[(E)-3-methoxy-3-oxoprop-1-enyl]-2,3-dihydro-1-benzofuran-3-carboxylate
• CAS: 1316855-24-9
• 化学式: C₂₂H₂₂O₉
• 分子量: 430.411
• InChiKey: PQTPLLMBZQFDNH-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  咖啡酸 在 manganese(IV) oxide 、 硫酸 、 双氧水 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.75h， 生成 methyl (E)-3-[2-(4-hydroxy-3,5-dimethoxyphenyl)-7-hydroxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]propen-2-enoate 、 dimethyl 7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate
  参考文献：
  名称：

  Horseradish peroxidase catalyzed oxidative cross-coupling reactions: the synthesis of ‘unnatural’ dihydrobenzofuran lignans

  摘要：

  The possibility to afford by a biomimetic reaction 'unnatural' products, which could offer a better bioactivity profile than natural analogues, is outlined and the first applications to the synthesis of lignans and related compounds have been reported. Here we describe the synthesis of new heterodimers, having a phenylcoumaran skeleton, by horseradish peroxidase catalyzed cross-coupling reactions of methyl esters of substituted hydroxycinnamic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.072

文献信息

• Horseradish peroxidase catalyzed oxidative cross-coupling reactions: the synthesis of ‘unnatural’ dihydrobenzofuran lignans
  作者：Francesco Saliu、Eeva-Liisa Tolppa、Luca Zoia、Marco Orlandi

  DOI：10.1016/j.tetlet.2011.05.072

  日期：2011.7

  The possibility to afford by a biomimetic reaction 'unnatural' products, which could offer a better bioactivity profile than natural analogues, is outlined and the first applications to the synthesis of lignans and related compounds have been reported. Here we describe the synthesis of new heterodimers, having a phenylcoumaran skeleton, by horseradish peroxidase catalyzed cross-coupling reactions of methyl esters of substituted hydroxycinnamic acids. (C) 2011 Elsevier Ltd. All rights reserved.