2-methyl-2-(4,8,11-trimethyldodeca-3,7,9-trienyl)-1,3-dioxolane | 1443663-01-1

• 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: 2-methyl-2-(4,8,11-trimethyldodeca-3,7,9-trienyl)-1,3-dioxolane
• CAS: 1443663-01-1
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: NNMVWKYJIGUHGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(4,8,11-trimethyldodeca-3,7,9-trienyl)-1,3-dioxolane 在 palladium 10% on activated carbon 、 氢气 、 草酸 作用下， 以 甲醇 、 正己烷 、 水 为溶剂， 20.0 ℃ 、172.37 kPa 条件下， 反应 3.5h， 生成 6,10,13-trimethyltetradecan-2-one
  参考文献：
  名称：

  (6R,10S)-Pallantione: The First Ketone Identified as Sex Pheromone in Stink Bugs

  摘要：

  This work describes the structural elucidation of the sex pheromone of the soybean stink bug, Pallantia macunaima. The biological activity of the synthetic pheromone was demonstrated by behavioral and EAD experiments. Furthermore, the absolute configuration of the natural pheromone was determined as (6R,10S)-6,10,13-trimethyltetradecan-2-one. This is the first ketone identified as a male-produced sex pheromone in Pentatomidae, and the trivial name, pallantione, was assigned to this novel pheromone molecule.

  DOI：

  10.1021/ol400413w
• 作为产物：
  描述：

  6,10-二甲基-5,9-十一双烯-2-酮 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 正丁基锂 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 20.66h， 生成 2-methyl-2-(4,8,11-trimethyldodeca-3,7,9-trienyl)-1,3-dioxolane
  参考文献：
  名称：

  (6R,10S)-Pallantione: The First Ketone Identified as Sex Pheromone in Stink Bugs

  摘要：

  This work describes the structural elucidation of the sex pheromone of the soybean stink bug, Pallantia macunaima. The biological activity of the synthetic pheromone was demonstrated by behavioral and EAD experiments. Furthermore, the absolute configuration of the natural pheromone was determined as (6R,10S)-6,10,13-trimethyltetradecan-2-one. This is the first ketone identified as a male-produced sex pheromone in Pentatomidae, and the trivial name, pallantione, was assigned to this novel pheromone molecule.

  DOI：

  10.1021/ol400413w