(1S,2R,5R)-5-[(2R)-6-methylhept-5-en-2-yl]bicyclo[3.1.0]hexan-2-ol | 1005411-87-9

• 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: (1S,2R,5R)-5-[(2R)-6-methylhept-5-en-2-yl]bicyclo[3.1.0]hexan-2-ol
• CAS: 1005411-87-9
• 化学式: C₁₄H₂₄O
• 分子量: 208.344
• InChiKey: YIWJDNVSSUOLEU-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R)-5-[(2R)-6-methylhept-5-en-2-yl]bicyclo[3.1.0]hexan-2-ol 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以100%的产率得到(6R,1'R,5'S)-2-methyl-6-(4'-oxobicyclo[3.1.0]hex-1'-yl)hept-2-ene
  参考文献：
  名称：

  Determination of the absolute configuration of the male aggregation pheromone, 2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol, of the stink bug Erysarcoris lewisi (Distant) as 2Z,6R,1′S,5′S by its synthesis

  摘要：

  Lipase-catalyzed asymmetric acetylation of a mixture of (6R,1'S,4'S,5'R)- and (6R,1'R,4'R,5'S)-7'-norsesquisabinen-4'-ol (3) afforded a separable mixture of the recovered former and the acetate of the latter. The recovered alcohol was oxidized to (6R,1'S,5'R)-sesquisabina ketone (2), whose absolute configuration could be assigned by its CD comparison with (1R,5S)-sabina ketone (4). Conversion of (6R,1'S,5'R)-sesquisabina ketone (2) to the bioactive pheromone revealed the stereostructure of the male aggregation pheromone of the stink bug Erysarcoris lewisi (Distant) to be (2Z,6R,1'S,5'S)-2-methyl-6-(4'-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol (sesquisabinen-1-ol, 1). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.036
• 作为产物：
  描述：

  [(1S,2R,5R)-5-[(2R)-6-methylhept-5-en-2-yl]-2-bicyclo[3.1.0]hexanyl] acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以100%的产率得到(1S,2R,5R)-5-[(2R)-6-methylhept-5-en-2-yl]bicyclo[3.1.0]hexan-2-ol
  参考文献：
  名称：

  Determination of the absolute configuration of the male aggregation pheromone, 2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol, of the stink bug Erysarcoris lewisi (Distant) as 2Z,6R,1′S,5′S by its synthesis

  摘要：

  Lipase-catalyzed asymmetric acetylation of a mixture of (6R,1'S,4'S,5'R)- and (6R,1'R,4'R,5'S)-7'-norsesquisabinen-4'-ol (3) afforded a separable mixture of the recovered former and the acetate of the latter. The recovered alcohol was oxidized to (6R,1'S,5'R)-sesquisabina ketone (2), whose absolute configuration could be assigned by its CD comparison with (1R,5S)-sabina ketone (4). Conversion of (6R,1'S,5'R)-sesquisabina ketone (2) to the bioactive pheromone revealed the stereostructure of the male aggregation pheromone of the stink bug Erysarcoris lewisi (Distant) to be (2Z,6R,1'S,5'S)-2-methyl-6-(4'-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol (sesquisabinen-1-ol, 1). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.036