(2R,3R)-3-Methyl-pentane-1,2-diol | 159623-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-3-Methyl-pentane-1,2-diol
• 英文别名: 1,2-Pentanediol, 3-methyl-, [R-(R*,R*)]-；(2R,3R)-3-methylpentane-1,2-diol
• CAS: 159623-53-7
• 化学式: C₆H₁₄O₂
• 分子量: 118.176
• InChiKey: OGLLAZUAZSIDFE-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  3
• 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：

  (2R,3R)-3-Methyl-pentane-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 (S,R)-Phoenicol
  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：

  顺-2-戊烯醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 (-)-diisopropyl-L-tartrate ((-)-DIPT) 作用下， 以 乙醚 为溶剂， 反应 17.0h， 生成 (2R,3R)-3-Methyl-pentane-1,2-diol
  参考文献：
  名称：

  Szurdoki, F.; Novak, L.; Baitz-Gacs, Eszter, Acta Chimica Hungarica, 1992, vol. 129, # 2, p. 303 - 309

  摘要：

  DOI：

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.
• Szurdoki, F.; Novak, L.; Baitz-Gacs, Eszter, Acta Chimica Hungarica, 1992, vol. 129, # 2, p. 303 - 309
  作者：Szurdoki, F.、Novak, L.、Baitz-Gacs, Eszter、Szantay, Cs.

  DOI：——

  日期：——