(2R,4R,4aR,7R,8aR)-4,7-dimethyl-2-(3,4,5-trimethoxyphenyl)octahydro-2H-chromen-4-ol | 1448612-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R,4R,4aR,7R,8aR)-4,7-dimethyl-2-(3,4,5-trimethoxyphenyl)octahydro-2H-chromen-4-ol
• CAS: 1448612-85-8
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: AWCZESQEEDSFED-LERAUJRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 异胡薄荷醇 在 三氟化硼乙醚 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (2R,4S,4aR,7R,8aR)-4,7-dimethyl-2-(3,4,5-trimethoxyphenyl)octahydro-2H-chromen-4-ol 、 (2R,4R,4aR,7R,8aR)-4,7-dimethyl-2-(3,4,5-trimethoxyphenyl)octahydro-2H-chromen-4-ol 、 、
  参考文献：
  名称：

  Influenza antiviral activity of F- and OH-containing isopulegol-derived octahydro-2H-chromenes

  摘要：

  We synthesized fluoro- and hydroxy-containing octahydro-2H-chromenes by the Prins reaction starting from a monoterpenoid (-)-isopulegol and a wide range of aromatic aldehydes in the presence of the BF₃∙Et₂O/H₂O system acting as both an acid catalyst and a fluorine source. Activity of the produced compounds against the influenza A/Puerto Rico/8/34 (H1N1) virus was studied. The highest activity was demonstrated by fluoro- (11i) and hydroxy-containing (10i) derivatives of 2,4,6-trimethoxybenzaldehyde. The most pronounced virus-inhibiting effect of compounds 10i and 11i was observed at an early stage of infection. These compounds were supposed to be capable of binding to viral hemagglutinin, which is an agreement with data on the effect of compounds 10i and 11i on the viral fusogenic activity as well as by molecular docking studies.

  DOI：

  10.1016/j.bmcl.2020.127677

文献信息

• Transformations of several monoterpenoids in the presence of aldehydes in supercritical solvents
  作者：V. I. Anikeev、V. P. Sivcev、I. V. Il’ina、D. V. Korchagina、O. B. Statsenko、K. P. Volcho、N. F. Salakhutdinov

  DOI：10.1134/s0036024413030023

  日期：2013.3

  The reactivity of verbenol epoxide and isopulegol in supercritical solvents in the presence of aromatic aldehydes was studied using a flow type reactor and a heterogeneous catalyst (Al2O3) or no catalyst. The intramolecular transformations or interactions of reagents with the solvent prevailed in all cases; the yield of the products of intermolecular reactions of terpenoids with aldehydes was up to 1%. The aldehydes did not interact with verbenol epoxide but produced a considerable effect on the distribution of its isomerization products.