1,2-(acetoxymethylenedioxy)-7,8-bis(benzyloxy)-4-(benzyloxycarbonyloxy)-3-(4-(benzyloxy)phenyl)-dibenzofuran | 1192737-28-2

• 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: 1,2-(acetoxymethylenedioxy)-7,8-bis(benzyloxy)-4-(benzyloxycarbonyloxy)-3-(4-(benzyloxy)phenyl)-dibenzofuran
• 英文别名: [8,9-Bis(phenylmethoxy)-5-phenylmethoxycarbonyloxy-4-(4-phenylmethoxyphenyl)-[1]benzofuro[2,3-g][1,3]benzodioxol-2-yl] acetate
• CAS: 1192737-28-2
• 化学式: C₅₀H₃₈O₁₁
• 分子量: 814.845
• InChiKey: IYHPAXGOENSNIK-UHFFFAOYSA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  61
• 可旋转键数：
  17
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2-(acetoxymethylenedioxy)-7,8-bis(benzyloxy)-4-(benzyloxycarbonyloxy)-3-(4-(benzyloxy)phenyl)-dibenzofuran 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 生成 Benzyl [1,2-dihydroxy-7,8-bis(phenylmethoxy)-3-(4-phenylmethoxyphenyl)dibenzofuran-4-yl] carbonate
  参考文献：
  名称：

  Structural elucidation and synthesis of vialinin C, a new inhibitor of TNF-α production

  摘要：

  A new inhibitor of TNF-alpha production (IC50 = 0.89 mu M) named vialinin C (1) was isolated from dry fruiting bodies of an edible Chinese mushroom, Thelephora vialis. The structure of 1 was determined by high-resolution MS, NMR spectroscopic analysis, and confirmed by synthesis. Synthesis of ganbajunin B (5) obtained from the same origin was also described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.058
• 作为产物：
  描述：

  7,8-bis(benzyloxy)-4-(benzyloxycarbonyloxy)-3-(4-(benzyloxy)phenyl)-1,2-methylenedioxydibenzofuran 、 lead(IV) tetraacetate 以 苯 为溶剂， 反应 4.0h， 以73%的产率得到1,2-(acetoxymethylenedioxy)-7,8-bis(benzyloxy)-4-(benzyloxycarbonyloxy)-3-(4-(benzyloxy)phenyl)-dibenzofuran
  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.
• Structural elucidation and synthesis of vialinin C, a new inhibitor of TNF-α production
  作者：Yue Qi Ye、Chiemi Negishi、Yayoi Hongo、Hiroyuki Koshino、Jun-ichi Onose、Naoki Abe、Shunya Takahashi

  DOI：10.1016/j.bmc.2014.02.058

  日期：2014.4

  A new inhibitor of TNF-alpha production (IC50 = 0.89 mu M) named vialinin C (1) was isolated from dry fruiting bodies of an edible Chinese mushroom, Thelephora vialis. The structure of 1 was determined by high-resolution MS, NMR spectroscopic analysis, and confirmed by synthesis. Synthesis of ganbajunin B (5) obtained from the same origin was also described. (C) 2014 Elsevier Ltd. All rights reserved.