4-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]-2H-furan-5-one

• 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: 4-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]-2H-furan-5-one
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: NNNUJNWMFLYQTF-JJWZBERDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]-2H-furan-5-one 在 aluminum oxide 作用下， 以 吡啶 为溶剂， 反应 8.0h， 以89%的产率得到villosin
  参考文献：
  名称：

  Expedient synthesis of villosin and its isomer (E)-labda-8(17),12,14-trien-15(16)-olide

  摘要：

  The synthesis of the title compounds has been achieved in concise, highly regiocontrolled fashion from commercially available (+)-sclareolide. In addition, we offer evidence that the structure of a newly reported natural product from Zingiber ottensii is incorrect. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.033
• 作为产物：
  描述：

  N-methoxy-N-methyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetamide 在 三氟甲磺酸二丁硼 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]-2H-furan-5-one
  参考文献：
  名称：

  Expedient synthesis of villosin and its isomer (E)-labda-8(17),12,14-trien-15(16)-olide

  摘要：

  The synthesis of the title compounds has been achieved in concise, highly regiocontrolled fashion from commercially available (+)-sclareolide. In addition, we offer evidence that the structure of a newly reported natural product from Zingiber ottensii is incorrect. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.033

文献信息

• Expedient synthesis of villosin and its isomer (E)-labda-8(17),12,14-trien-15(16)-olide
  作者：John Boukouvalas、Jian-Xin Wang、Olivier Marion

  DOI：10.1016/j.tetlet.2007.09.033

  日期：2007.10

  The synthesis of the title compounds has been achieved in concise, highly regiocontrolled fashion from commercially available (+)-sclareolide. In addition, we offer evidence that the structure of a newly reported natural product from Zingiber ottensii is incorrect. (C) 2007 Elsevier Ltd. All rights reserved.