vialinin B

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: vialinin B
• 英文别名: [4,7,8-trihydroxy-3-(4-hydroxyphenyl)-1-(2-phenylacetyl)oxydibenzofuran-2-yl] 2-phenylacetate
• 化学式: C₃₄H₂₄O₉
• 分子量: 576.559
• InChiKey: FMUSGJFTMXBKQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,2-bis(phenylacetyloxy)-7,8-bis(benzyloxy)-4-(benzyloxycarbonyloxy)-3-(4-(benzyloxy)-phenyl)dibenzofuran 在 氢气 、 palladium(II) hydroxide 作用下， 以 乙酸乙酯 为溶剂， 反应 14.0h， 以89%的产率得到vialinin B
  参考文献：
  名称：

  Expeditious Synthesis of Vialinin B, an Extremely Potent Inhibitor of TNF-α Production

  摘要：

  A first total synthesis of vialinin B, a powerful inhibitor (IC50 20 pM) of TNF-alpha production, is described. The key reactions include a double Suzuki-Miyaura coupling of electron-rich aryl bromide with a couple of phenylboronic acids, a Cu-mediated Ullmann reaction, and a LHMDS-promoted phenylacetylation. This synthesis proceeded in 11 steps with 18% overall yield from a known sesamol derivative.

  DOI：

  10.1021/ol9020833

文献信息

• Expeditious Synthesis of Vialinin B, an Extremely Potent Inhibitor of TNF-α Production
  作者：Yue Qi Ye、Hiroyuki Koshino、Jun-ichi Onose、Kunie Yoshikawa、Naoki Abe、Shunya Takahashi

  DOI：10.1021/ol9020833

  日期：2009.11.5

  A first total synthesis of vialinin B, a powerful inhibitor (IC50 20 pM) of TNF-alpha production, is described. The key reactions include a double Suzuki-Miyaura coupling of electron-rich aryl bromide with a couple of phenylboronic acids, a Cu-mediated Ullmann reaction, and a LHMDS-promoted phenylacetylation. This synthesis proceeded in 11 steps with 18% overall yield from a known sesamol derivative.