(3S,3aS,6aR)-3,6-Dimethyl-3,3a,4,6a-tetrahydro-2H-pentalen-1-one | 89822-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,3aS,6aR)-3,6-Dimethyl-3,3a,4,6a-tetrahydro-2H-pentalen-1-one
• CAS: 89822-36-6
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: GSTWQECWTKNXDD-NRPADANISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (3S,3aS,6aR)-3,6-Dimethyl-3,3a,4,6a-tetrahydro-2H-pentalen-1-one 在 palladium on activated charcoal 氢气 、 二异丁基氢化铝 、 对甲苯磺酸 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 环己烷 为溶剂， 反应 6.0h， 生成 cis,cis-Nepetalactol
  参考文献：
  名称：

  The Potential of Semiochemicals for Control ofPhorodon humuli(Homoptera: Aphididae)

  摘要：

  Field experiments employing yellow water-traps with vials releasing methyl salicylate, butyl isothiocyanate, 4-pentenyl isothiocyanate and diethyltoluamide were conducted during the spring migration of Phorodon humuli (Schrank), with the aim of identifying substances which might be used in the field to deter landing on hop plants. Methyl salicylate and the two isothiocyanates reduced trap catches of P. humuli. During the spring of 1994 a slow-release formulation of methyl salicylate and a beta-acid-rich hop resin sprayed on to hop plants did not reduce aphid infestations significantly. In autumn cis,cis-nepetalactol the main component of P. humuli's sex pheromone, prepared by various synthetic routes, increased trap catches of males and gynoparae equally. Catches of males in pheromone traps situated in a hop garden decreased with increasing trap height. Catches of males in traps charged with increasing doses of the cis,cis-nepetalactol peaked at 1 mg and then plateaued, whereas catches of gynoparae peaked similarly at 1 mg and then decreased. The effects of kairomones from an extract of the primary host, sex pheromone and a visual cue from yellow compared with clear water-traps were additive. The prospects for developing a semiochemicals-based control strategy against P. humuli, using some or all of the above elements, are discussed.

  DOI：

  10.1002/(sici)1096-9063(199612)48:4<293::aid-ps479>3.0.co;2-5
• 作为产物：
  描述：

  (3S,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one 在 potassium hydrogensulfate 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以80%的产率得到(3S,3aS,6aR)-3,6-Dimethyl-3,3a,4,6a-tetrahydro-2H-pentalen-1-one
  参考文献：
  名称：

  The Potential of Semiochemicals for Control ofPhorodon humuli(Homoptera: Aphididae)

  摘要：

  Field experiments employing yellow water-traps with vials releasing methyl salicylate, butyl isothiocyanate, 4-pentenyl isothiocyanate and diethyltoluamide were conducted during the spring migration of Phorodon humuli (Schrank), with the aim of identifying substances which might be used in the field to deter landing on hop plants. Methyl salicylate and the two isothiocyanates reduced trap catches of P. humuli. During the spring of 1994 a slow-release formulation of methyl salicylate and a beta-acid-rich hop resin sprayed on to hop plants did not reduce aphid infestations significantly. In autumn cis,cis-nepetalactol the main component of P. humuli's sex pheromone, prepared by various synthetic routes, increased trap catches of males and gynoparae equally. Catches of males in pheromone traps situated in a hop garden decreased with increasing trap height. Catches of males in traps charged with increasing doses of the cis,cis-nepetalactol peaked at 1 mg and then plateaued, whereas catches of gynoparae peaked similarly at 1 mg and then decreased. The effects of kairomones from an extract of the primary host, sex pheromone and a visual cue from yellow compared with clear water-traps were additive. The prospects for developing a semiochemicals-based control strategy against P. humuli, using some or all of the above elements, are discussed.

  DOI：

  10.1002/(sici)1096-9063(199612)48:4<293::aid-ps479>3.0.co;2-5