(2S,3S)-3-Methyl-hexane-1,2-diol | 159700-68-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S)-3-Methyl-hexane-1,2-diol
• 英文别名: (2S,3S)-3-methylhexane-1,2-diol
• CAS: 159700-68-2
• 化学式: C₇H₁₆O₂
• 分子量: 132.203
• InChiKey: MSCWGJFHWUZSAO-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-Methyl-hexane-1,2-diol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙醚 为溶剂， 反应 7.5h， 生成 trans-5-methyloct-4-ol
  参考文献：
  名称：

  Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

  摘要：

  There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil, Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil, Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by male R. phoenicis and male R. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, with R. phoenicis in Cote d'Ivoire and R. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,SS)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.

  DOI：

  10.1007/bf02036199
• 作为产物：
  描述：

  三甲基铝 、 (2S,3S)-(-)-3-丙基环氧乙烷甲醇 在 正丁基锂 作用下， 以 正戊烷 为溶剂， 反应 0.5h， 以70%的产率得到(2S,3S)-3-Methyl-hexane-1,2-diol
  参考文献：
  名称：

  Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

  摘要：

  There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil, Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil, Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by male R. phoenicis and male R. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, with R. phoenicis in Cote d'Ivoire and R. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,SS)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.

  DOI：

  10.1007/bf02036199

文献信息

• Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)
  作者：Alice L. Perez、Gerhard Gries、Regine Gries、Robin M. Giblin-Davis、A. Cameron Oehlschlager

  DOI：10.1007/bf02036199

  日期：1994.10

  There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil, Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil, Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by male R. phoenicis and male R. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, with R. phoenicis in Cote d'Ivoire and R. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,SS)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.