trans-1-[4-(2,2-Dibromovinyl)cyclohexyl]-4-tert-butyl-2,6,7-trioxabicyclo[2.2.2]octane | 121318-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-1-[4-(2,2-Dibromovinyl)cyclohexyl]-4-tert-butyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS: 121318-07-8
• 化学式: C₁₇H₂₆Br₂O₃
• 分子量: 438.2
• InChiKey: PHSBGBHYLIAUSA-STZBCSTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trans-1-[4-(2,2-Dibromovinyl)cyclohexyl]-4-tert-butyl-2,6,7-trioxabicyclo[2.2.2]octane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以0.45 g的产率得到trans-4-tert-Butyl-1-(4-ethynylcyclohexyl)-2,6,7-trioxabicyclo[2.2.2]octane
  参考文献：
  名称：

  Insecticidal isomers of 4-tert-butyl-1-(4-ethynylcyclohexyl)-2,6,7-trioxabicyclo [2.2.2] octane and 5-tert-butyl-2-(4-ethynylcyclohexyl)-1,3-dithiane

  摘要：

  Abstract4‐tert‐Butyl‐2,6,7‐trioxabicyclo[2.2.2]octanes and 5‐tert‐butyl‐1,3‐dithianes with the 4‐ethynylcyclohexyl substituent in the 1‐ and 2‐positions, respectively, are potent insecticides modeled on their 4‐ethynylphenyl and hex‐5‐ynyl analogs. The compounds were prepared from dimethyl 1,4‐cyclohexanedicarboxylate, 4‐(2,2‐dibromovinyl)cyclohexanecarboxylic acid, methyl 4‐(1‐chlorovinyl)cyclohexanecarboxylate, and 4‐ethynylcyclohexylmethanol by wellestablished chemistry. The cis and trans isomers of the 1‐cyclohexyl‐trioxabicyclooctane and all four geometric isomers of the 2‐cyclohexyl‐1,3‐dithiane were separated by chromatography of the final products or suitable intermediates. High levels of insecticidal activity were found against houseflies, German cockroaches and aphids for trioxabicyclooctanes and dithianes with the trans ethynylcyclohexyl configuration.

  DOI：

  10.1002/ps.2780440110
• 作为产物：
  描述：

  trans-4-(2,2-Dibromovinyl)cyclohexanecarboxylic acid chloride 在 吡啶 、 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 trans-1-[4-(2,2-Dibromovinyl)cyclohexyl]-4-tert-butyl-2,6,7-trioxabicyclo[2.2.2]octane
  参考文献：
  名称：

  Insecticidal isomers of 4-tert-butyl-1-(4-ethynylcyclohexyl)-2,6,7-trioxabicyclo [2.2.2] octane and 5-tert-butyl-2-(4-ethynylcyclohexyl)-1,3-dithiane

  摘要：

  Abstract4‐tert‐Butyl‐2,6,7‐trioxabicyclo[2.2.2]octanes and 5‐tert‐butyl‐1,3‐dithianes with the 4‐ethynylcyclohexyl substituent in the 1‐ and 2‐positions, respectively, are potent insecticides modeled on their 4‐ethynylphenyl and hex‐5‐ynyl analogs. The compounds were prepared from dimethyl 1,4‐cyclohexanedicarboxylate, 4‐(2,2‐dibromovinyl)cyclohexanecarboxylic acid, methyl 4‐(1‐chlorovinyl)cyclohexanecarboxylate, and 4‐ethynylcyclohexylmethanol by wellestablished chemistry. The cis and trans isomers of the 1‐cyclohexyl‐trioxabicyclooctane and all four geometric isomers of the 2‐cyclohexyl‐1,3‐dithiane were separated by chromatography of the final products or suitable intermediates. High levels of insecticidal activity were found against houseflies, German cockroaches and aphids for trioxabicyclooctanes and dithianes with the trans ethynylcyclohexyl configuration.

  DOI：

  10.1002/ps.2780440110