9-geranyl-α-terpineol

• 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: 9-geranyl-α-terpineol
• 英文别名: (5E)-6,10-dimethyl-2-(4-methylcyclohex-3-en-1-yl)undeca-5,9-dien-2-ol
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: YGPABMQZQTXEOE-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-geranyl-α-terpineol 在 吡啶 、 三氯氧磷 作用下， 反应 50.0h， 生成 2,6-dimethyl-10-(4-methyl-3-cyclohexene-1-ylid-4E-ene)-2,6E-undecadiene 、 2,6-dimethyl-10-(4-methyl-3-cyclohexene-1-ylid-4Z-ene)-2,6E-undecadiene 、 E,Z-2,6-dimethyl-10-(4-methyl-3-cyclohexenyl)-2,6,9-undecatriene 、 E,E-2,6-dimethyl-10-(4-methyl-3-cyclohexenyl)-2,6,9-undecatriene 、 E-6,10-dimethyl-2-(4-methyl-3-cyclohexenyl)-1,5,9-undecatriene 、 E-6,10-dimethyl-2-(3-methyl-3-cyclohexenyl)-1,5,9-undecatriene
  参考文献：
  名称：

  Synthesis of 9-geranylterpinolene as a mixture of isomers, and synthesis of α- and β-springene, possible kairomones of the beech leaf-mining weevil, Orchestes fagi (L.)

  摘要：

  The beech leaf-mining weevil, Orchestes fagi (L.), also known as the beech flea weevil, is a common and widespread pest of beech, Fagus sylvatica L., in its native Europe. It now appears to be well established in Nova Scotia, Canada. We have previously reported the synthesis of 9-geranyl-p-cymene and 9-geranyl--terpinene, as they are both found in eclosing beech buds, and have researched the synthesis of other diterpenes that are isomers of 9-geranyl--terpinene. We now wish to report a synthesis of the diterpene 9-geranylterpinolene as a mixture of isomers, as a novel diterpene, and as a possible kairomone of O. fagi. Also, all trans--springene, its 3Z-isomer, and -springene were synthesized as a mixture, as well as pure -springene, utilizing known methods.[GRAPHICS].

  DOI：

  10.1080/00397911.2018.1463544
• 作为产物：
  描述：

  4-乙酰基-1-甲基-环己烯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 20.5h， 生成 9-geranyl-α-terpineol
  参考文献：
  名称：

  Synthesis of 9-geranylterpinolene as a mixture of isomers, and synthesis of α- and β-springene, possible kairomones of the beech leaf-mining weevil, Orchestes fagi (L.)

  摘要：

  The beech leaf-mining weevil, Orchestes fagi (L.), also known as the beech flea weevil, is a common and widespread pest of beech, Fagus sylvatica L., in its native Europe. It now appears to be well established in Nova Scotia, Canada. We have previously reported the synthesis of 9-geranyl-p-cymene and 9-geranyl--terpinene, as they are both found in eclosing beech buds, and have researched the synthesis of other diterpenes that are isomers of 9-geranyl--terpinene. We now wish to report a synthesis of the diterpene 9-geranylterpinolene as a mixture of isomers, as a novel diterpene, and as a possible kairomone of O. fagi. Also, all trans--springene, its 3Z-isomer, and -springene were synthesized as a mixture, as well as pure -springene, utilizing known methods.[GRAPHICS].

  DOI：

  10.1080/00397911.2018.1463544