(2S,4R,4aR,8R,8aR)-4,7-dimethyl-2-(2,4,5-trimethoxyphenyl)-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol | 1415323-69-1

• 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: (2S,4R,4aR,8R,8aR)-4,7-dimethyl-2-(2,4,5-trimethoxyphenyl)-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol
• CAS: 1415323-69-1
• 化学式: C₂₀H₂₈O₆
• 分子量: 364.439
• InChiKey: VQLFWWDMKWFUJN-WNTFAFMFSA-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：

  (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol 、 2,4,5-三甲氧基苯甲醛 在 montmorillonite K 10 clay 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以34%的产率得到
  参考文献：
  名称：

  Mikhalchenko, Oksana S.; Korchagina, Dina V.; Volcho, Konstantin P., Helvetica Chimica Acta, 2014, vol. 97, # 10, p. 1406 - 1421

  摘要：

  DOI：

文献信息

• Synthesis and analgesic activity of new heterocyclic compounds derived from monoterpenoids
  作者：Oksana Mikhalchenko、Irina Il’ina、Alla Pavlova、Ekaterina Morozova、Dina Korchagina、Tat’yana Tolstikova、Evgeny Pokushalov、Konstantin Volcho、Nariman Salakhutdinov

  DOI：10.1007/s00044-012-0310-9

  日期：2013.6

  set of new heterocyclic compounds with different types of framework, including a new type of framework, were synthesized by reactions of verbenol epoxide and (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aromatic aldehydes containing three methoxy groups. The analgesic activity of these substances was studied. Three compounds possessed considerable activity in vivo in the acetic

  合成了具有不同骨架类型的一组新型杂环化合物，其中包括一种新型骨架，是由马来酸环氧化物与（1 R，2 R，6 S）-3-甲基-6-（prop-1-en）反应合成的-2-基）环己-3-烯-1，2-二醇与含有三个甲氧基的芳香醛。研究了这些物质的镇痛活性。三种化合物在乙酸诱导的扭体试验中具有相当大的体内活性。（2 S，4 R，4a R，8 S，8a R）-4,7-二甲基-2-（2,4,5-三甲氧基苯基）-3,4,4a，5,8,8a-hexahydro-2 H-4,8-​​环氧丙烷在乙酸诱导的扭体试验和热板试验中均显示出高镇痛活性；选择性指数IS 50超过60。
• Anti-influenza activity of monoterpene-derived substituted hexahydro-2 H -chromenes
  作者：Oksana S. Patrusheva、Vladimir V. Zarubaev、Anna A. Shtro、Yana R. Orshanskaya、Sergey A. Boldyrev、Irina V. Ilyina、Svetlana Yu. Kurbakova、Dina V. Korchagina、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.1016/j.bmc.2016.08.037

  日期：2016.11

  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.