(E)-2-(4-benzyloxy-3-methoxyphenyl)-5-(3-acetoxypropenyl)-7-methoxybenzofuran | 515814-07-0

• 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: (E)-2-(4-benzyloxy-3-methoxyphenyl)-5-(3-acetoxypropenyl)-7-methoxybenzofuran
• 英文别名: [(E)-3-[7-methoxy-2-(3-methoxy-4-phenylmethoxyphenyl)-1-benzofuran-5-yl]prop-2-enyl] acetate
• CAS: 515814-07-0
• 化学式: C₂₈H₂₆O₆
• 分子量: 458.511
• InChiKey: HAMQJPQQWQMNHZ-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-benzyloxy-3-methoxyphenyl)-5-(3-acetoxypropenyl)-7-methoxybenzofuran 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 8.0h， 以98%的产率得到2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxypropyl)-7-methoxybenzofuran
  参考文献：
  名称：

  Total Synthesis of Ailanthoidol and Precursor XH14 by Stille Coupling

  摘要：

  Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the synthesis are the Stille coupling reactions of benzofuranyl bromide with stannanyl compounds. This synthetic strategy can be modified to give access to a variety of different ailanthoidol and XH14 analogues.

  DOI：

  10.1021/jo020653t
• 作为产物：
  描述：

  5-溴-2-羟基-3-甲氧基苯甲醛 在 吡啶 、 四(三苯基膦)钯 、 三溴化磷 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 14.33h， 生成 (E)-2-(4-benzyloxy-3-methoxyphenyl)-5-(3-acetoxypropenyl)-7-methoxybenzofuran
  参考文献：
  名称：

  Total Synthesis of Ailanthoidol and Precursor XH14 by Stille Coupling

  摘要：

  Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the synthesis are the Stille coupling reactions of benzofuranyl bromide with stannanyl compounds. This synthetic strategy can be modified to give access to a variety of different ailanthoidol and XH14 analogues.

  DOI：

  10.1021/jo020653t

文献信息

• Total Synthesis of Ailanthoidol and Precursor XH14 by Stille Coupling
  作者：Shun-Yu Lin、Chih-Lung Chen、Yean-Jang Lee

  DOI：10.1021/jo020653t

  日期：2003.4.1

  Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the synthesis are the Stille coupling reactions of benzofuranyl bromide with stannanyl compounds. This synthetic strategy can be modified to give access to a variety of different ailanthoidol and XH14 analogues.