2,7-dimethyl-4,6-octadien-1-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,7-dimethyl-4,6-octadien-1-ol
• 英文别名: 2,7-dimethylocta-4,6-dienol；2,7-dimethylocta-4,6-dien-1-ol
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: VOPMCHBWEUCZJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,7-dimethyl-4,6-octadien-1-ol 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ palladium diacetate 、 三异丁基铝 、 1,2-双(二苯基膦)乙烷 、 对苯醌 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 38.0h， 生成 3,5-cis-marmelo oxide
  参考文献：
  名称：

  Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols

  摘要：

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.

  DOI：

  10.1021/jo00018a027
• 作为产物：
  描述：

  diethyl 2-methyl-2-((E)-5-methyl-2,4-hexadien-1-yl)-malonate 在 氰化钠 、 水 、 二异丁基氢化铝 作用下， 以 正己烷 、 二甲基亚砜 为溶剂， 反应 5.5h， 生成 2,7-dimethyl-4,6-octadien-1-ol
  参考文献：
  名称：

  Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols

  摘要：

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.

  DOI：

  10.1021/jo00018a027

文献信息

• Aluminium Triflate Catalysed Cyclisation of Unsaturated Alcohols: Novel Synthesis of Rose Oxide and Analogues
  作者：Lydie Coulombel、Michel Weïwer、Elisabet Duñach

  DOI：10.1002/ejoc.200900841

  日期：2009.11

  Aluminium trifluoromethanesulfonate was used as an efficient catalyst for the cycloisomerisation of several unsaturated alcohols into cyclic ethers such as rose oxide and some of its ether analogues. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  三氟甲磺酸铝被用作将几种不饱和醇环异构化成环醚（如玫瑰氧化物及其一些醚类似物）的有效催化剂。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Synthesis of furanoid terpenes via an efficient palladium-catalyzed cyclization of 4,6-dienols
  作者：Pher G. Andersson、Jan E. Baeckvall

  DOI：10.1021/jo00018a027

  日期：1991.8

  The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.