(11R,S)-11-(2',5'-dimethoxy-1'-phenyl)drim-8(12)-en-11-ol | 455331-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (11R,S)-11-(2',5'-dimethoxy-1'-phenyl)drim-8(12)-en-11-ol
• 英文别名: [(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-(2,5-dimethoxyphenyl)methanol
• CAS: 455331-73-4
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: XYXCUPWTGDWGNR-MXHMCPQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (11R,S)-11-(2',5'-dimethoxy-1'-phenyl)drim-8(12)-en-11-ol 在 lithium 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 0.25h， 以97%的产率得到(+)-zonarol dimethyl ether
  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
• 作为产物：
  描述：

  (1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl-methanol 在 仲丁基锂 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 0.58h， 生成 (11R,S)-11-(2',5'-dimethoxy-1'-phenyl)drim-8(12)-en-11-ol
  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 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.