(2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol | 1292847-75-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol
• CAS: 1292847-75-6
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: DTOUXULHWPNTNK-JJTUDDRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (1S)-(-)-verbenone 在 双氧水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2S,4R,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol 、 (2S,4S,4aR,8R,8aR)-3,4,4a,5,8,8a-hexahydro-4,7-dimethyl-2-phenyl-2H-chromene-4,8-diol
  参考文献：
  名称：

  含有烷基取代芳族部分的 4,7-Dimethyl-3,4,4a,5,8,8a-Hexahydro-2-Chromen-4,8-​​Diols 的合成和镇痛活性

  摘要：

  通过对单萜对薄荷醇1,8-二烯-5,6-二醇与4-烷基取代的芳香醛反应，制备了一系列具有六氢-2H-色烯骨架的新型杂环化合物。与与苯甲醛的类似反应相比，向醛芳环中添加小的烷基取代基（甲基和乙基）可提高六氢色烯的产率。然而，添加支链取代基（异丙基）和更长的丁基和辛基部分会降低目标化合物的产率。随着烷基取代基的延长，反应的立体选择性发生变化。研究了所得产物的镇痛活性。

  DOI：

  10.1007/s10600-017-2202-1

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。
• 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.