(2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol | 1292847-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol
• 英文别名: (2S,4aR,8R,8aR)-4a,5,8,8a-tetrahydro-4,4,7-trimethyl-2-phenyl-4H-1,3-benzodioxin-8-ol；(2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-1,3-benzodioxin-8-ol
• CAS: 1292847-77-8
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: IRTQWFXAUHHTJX-FPCVCCKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 、 (1R,2R,4S,5R,6S)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^4.2]octan-5-ol 在 5 wtpercentFe-H-Beta-SiO₂/Al₂O₃=150 zeolite 作用下， 以 甲苯 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol 、 (S)-2-hydroxy-1-(2,2,3-trimethylcyclopent-3-enyl)ethanone 、 (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol 、 (2S,4S,4aR,8R,8aR)-4,7-dimethyl-2-phenyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol
  参考文献：
  名称：

  Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: Synthesis of monoterpenoid dioxinols with analgesic activity

  摘要：

  Catalytic synthesis of a dioxinol compound, (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol, exhibiting analgesic activity was demonstrated over Femodified beta zeolite. During interactions between cis-verbenol oxide and benzaldehyde, two main reactions occurred. In the first reaction, namely isomerization of verbenol oxide both cyclopentenic hydroxyketone, oxetane as well as a cyclohexyl compound, (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol were formed. In the second parallel reaction the target compound was generated. The highest yield of the target compound was achieved in the reaction between verbenol oxide and benzaldehyde at their molar ratio of 1:133 with the bifunctional iron modified Fe-H-Beta-150 catalyst at 70 degrees C giving a much higher yield than reported earlier in the literature, being 46 mol-% at complete conversion of verbenol oxide. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2014.10.023

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。