mertensene | 90024-68-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: mertensene
• 英文别名: (1R,2R,4S,5R)-4-bromo-1,2-dichloro-5-[(E)-2-chlorovinyl]-1,5-dimethyl-cyclohexane；(1R,2R,4S,5R)-4-bromo-1,2-dichloro-5-[(E)-2-chloroethenyl]-1,5-dimethylcyclohexane
• CAS: 90024-68-3
• 化学式: C₁₀H₁₄BrCl₃
• 分子量: 320.484
• InChiKey: RUGBKCUWZCCZDR-GXFJTLABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  mertensene 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以22 mg的产率得到(R)-4-((E)-2-Chloro-vinyl)-2,4-dimethyl-cyclohexa-2,5-dienone
  参考文献：
  名称：

  Antifeedant Effects of Marine Halogenated Monoterpenes

  摘要：

  In this work the antifeedant effects of the halogenated monoterpenes 1-13 were tested against several divergent insect species. These compounds have been isolated from Plocamium cartilagineum (6 was isolated as an acetyl derivative), except for 4, which was isolated from Pantoneura plocamioides. We have also included the semisynthetic derivatives 1a, 2a, and 7. Compounds 1, 1a, 2, 4, 5, 7, 8-10, and 13 were antifeedants against Leptinotarsa decemlineata with varying potencies. The aphids Myzus persicae and Ropalosiphum padi were strongly deterred in the presence of compounds 2, 12, and 13. This effect was correlated with the electronic recording of their probing behavior. Compounds 2 and 12 were toxic to L. decemlineata and had selective cytotoxicity to insect-derived Sf9 cells. None of the tested compounds showed phytotoxic effects. The antifeedant and cytotoxic effects of these compounds were compared with those of the polyhalogenated insecticide gamma-hexachlorocyclohexane (lindane).

  DOI：

  10.1021/jf025857p

文献信息

• Antifeedant Effects of Marine Halogenated Monoterpenes
  作者：Victor H. Argandoña、Juana Rovirosa、Aurelio San-Martín、Alejandro Riquelme、Ana R. Díaz-Marrero、Mercedes Cueto、José Darias、Omar Santana、Ana Guadaño、Azucena González-Coloma

  DOI：10.1021/jf025857p

  日期：2002.11.1

  In this work the antifeedant effects of the halogenated monoterpenes 1-13 were tested against several divergent insect species. These compounds have been isolated from Plocamium cartilagineum (6 was isolated as an acetyl derivative), except for 4, which was isolated from Pantoneura plocamioides. We have also included the semisynthetic derivatives 1a, 2a, and 7. Compounds 1, 1a, 2, 4, 5, 7, 8-10, and 13 were antifeedants against Leptinotarsa decemlineata with varying potencies. The aphids Myzus persicae and Ropalosiphum padi were strongly deterred in the presence of compounds 2, 12, and 13. This effect was correlated with the electronic recording of their probing behavior. Compounds 2 and 12 were toxic to L. decemlineata and had selective cytotoxicity to insect-derived Sf9 cells. None of the tested compounds showed phytotoxic effects. The antifeedant and cytotoxic effects of these compounds were compared with those of the polyhalogenated insecticide gamma-hexachlorocyclohexane (lindane).