(2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-(3,4,5-trimethoxyphenyl)-2H-chromene-4,8-diol | 1292847-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-(3,4,5-trimethoxyphenyl)-2H-chromene-4,8-diol
• CAS: 1292847-86-9
• 化学式: C₂₀H₂₈O₆
• 分子量: 364.439
• InChiKey: FLHMFQZNJJPWBH-DLCPYMQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  马鞭草烯醇 在 三氟化硼乙醚 、 水 、 双氧水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,4R,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-(3,4,5-trimethoxyphenyl)-2H-chromene-4,8-diol 、 (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-(3,4,5-trimethoxyphenyl)-2H-chromene-4,8-diol 、 、
  参考文献：
  名称：

  Anti-influenza activity of monoterpene-derived substituted hexahydro-2 H -chromenes

  摘要：

  The antiviral activity of 4-hydroxy-hexahydro-2H-chromenes and 4-fluorine-hexahydro-2H-chromenes with an aromatic substituent, synthesized from monoterpene (-)-verbenone, was studied for the first time. Five of 11 (45 per cent) of 4-hydroxy-hexahydro-2H-chromene-type compounds have been found to exhibit antiviral activity against influenza A virus of subtype H1N1pdm09. Although a portion of active compounds among 4-fluorine-containing series was fewer, just compound 5i that contains a fluorine substituent exhibited more potent anti-influenza activity along with low cytotoxicity. Thus two new promising types of antiviral compounds were identified. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.08.037

文献信息

• Reactions of Verbenol Epoxide with Aromatic Aldehydes Containing Hydroxy or Methoxy Groups in the Presence of Montmorillonite Clay
  作者：Irina V. Il'ina、Konstantin P. Volcho、Oksana S. Mikhalchenko、Dina V. Korchagina、Nariman F. Salakhutdinov

  DOI：10.1002/hlca.201000269

  日期：2011.3

  The reactions of (−)‐cis‐verbenol epoxide with a number of aromatic aldehydes containing OH and/or MeO groups in the presence of montmorillonite K10 clay have been studied. Several new O‐containing heterocyclic compounds with different frameworks, including compounds with a previously unknown octahydro‐2H‐4,6‐(epoxymethano)chromene framework, have been synthesized. Introduction of one donor substituent

  研究了在蒙脱土K10粘土存在下（-）-顺式-邻苯二酚-环氧化合物与许多含有OH和/或MeO基团的芳族醛的反应。已经合成了几种具有不同骨架的新的含O杂环化合物，包括具有未知的八氢-2 H - 4,6-（环氧亚甲基）色烯骨架的化合物。在苯甲醛分子中引入一个供体取代基导致分子间副产物的总产率降低，而引入两个或更多个取代基导致这些产物的产率提高。