yahazunol | 69809-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: yahazunol
• 英文别名: 2-[[(1S,2S,4aR,8aR)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]benzene-1,4-diol
• CAS: 69809-36-5
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: ZXQLWSVBDXTOCU-JYRKZWEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl-methanol 在 palladium on activated charcoal 吡啶-2,6-二羧酸 n-氧化物 、 lithium aluminium tetrahydride 、 sodium dithionite 、 ammonium cerium(IV) nitrate 、 氢气 、 仲丁基锂 、 lithium 、 potassium carbonate 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 环己烷 、 氨 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 42.58h， 生成 yahazunol
  参考文献：
  名称：

  Total synthesis of yahazunol, zonarone and isozonarone

  摘要：

  The synthesis of the marine natural products zonarone and isozonarone was achieved via (+)-albicanic acid, a sesquiterpene of the drimane type. Coupling of the appropiate drimane-synthon with lithiated hydroquinone ethers led to sesquiterpene arenes, which were further modified to the target molecules. Stereoselective epoxidation followed by regioselective opening of the oxirane ring yielded yahazunol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00346-0

文献信息

• Total synthesis of two 12-nordrimanes and the pharmacological active sesquiterpene hydroquinone yahazunol
  作者：Thorsten Laube、Winfried Beil、Karlheinz Seifert

  DOI：10.1016/j.tet.2004.11.059

  日期：2005.1

  The synthesis of two 12-nordrimanes and yahazunol was achieved via 8-oxo-12-nordrimanic acid methyl ester. The cytotoxic activity of yahazunol and seven other sesquiterpene hydroquinones and sesquiterpene quinones has been determined. (C) 2004 Elsevier Ltd. All rights reserved.
• Total synthesis of yahazunol, zonarone and isozonarone
  作者：Thorsten Laube、Jörg Schröder、Ralf Stehle、Karlheinz Seifert

  DOI：10.1016/s0040-4020(02)00346-0

  日期：2002.5

  The synthesis of the marine natural products zonarone and isozonarone was achieved via (+)-albicanic acid, a sesquiterpene of the drimane type. Coupling of the appropiate drimane-synthon with lithiated hydroquinone ethers led to sesquiterpene arenes, which were further modified to the target molecules. Stereoselective epoxidation followed by regioselective opening of the oxirane ring yielded yahazunol. (C) 2002 Elsevier Science Ltd. All rights reserved.