[(3S)-oct-1-en-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 99618-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3S)-oct-1-en-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 99618-83-4
• 化学式: C₁₈H₂₃F₃O₃
• 分子量: 344.374
• InChiKey: CDHVSNUDWMUYRO-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [(3S)-oct-1-en-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 在 sodium borotritide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  The aphid sex pheromone cyclopentanoids: Synthesis in the elucidation of structure and biosynthetic pathways

  摘要：

  Identification of a range of aphid sex pheromones as comprising the cyclopentanoids (4aS,7S,7aR)-nepetalactune, (1R,4aS,7S,7aR)-nepetalactol and the (1S)- and (1R,4aR,7S,7aS)-nepetalactols required samples authenticated by H-1 and C-13 NMR. These and related compounds were provided by small scale synthesis and extraction from plants in the genus Nepeta (Lamiaceae). The subsequent discovery that the synthetic sex pheromones could attract males, and also parasitic wasps that attack aphids, has created a need for large scale syntheses of the cyclopentanoids. This is afforded by cyclisation of the 8-oxo-1-enamine of citronellal as originally developed by Schreiber and co-workers (1986). Investigation into the biosynthesis of the cyclopentanoids by plants for exploiting aphid sex pheromones in crop protection by means of molecular biology required synthesis of putative biosynthetic intermediates, some with radioactive isotopic labelling, particularly 8-oxidised monoterpene alcohols and aldehydes. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00012-0
• 作为产物：
  描述：

  1-辛烯-3-醇 、 (S)-(-)-α-甲氧基-α-(三氟甲基)苯乙酸 生成 [(3S)-oct-1-en-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  MOSANDL A.; GESS. NER, M.; HEUSINGER G., LEBENSMITTELCHEM. UND GERICHTL. CHEM., 41,(1987) N 1, 19-20

  摘要：

  DOI：

文献信息

• Assignment of absolute stereochemistry to an insect pheromone by chiral amplification
  作者：Xiongwei Shi、Walter S. Leal、Jerrold Meinwald

  DOI：10.1016/0968-0896(96)00006-5

  日期：1996.3

  Chiral amplification, a new strategy for determining the absolute configuration of difficultly available natural secondary alcohols or analogous amines; is described. Using this technique. the R configuration can be assigned to both components of the male sex pheromone emitted by the longhorn beetle, Anaglyptus subfasciatus. The application of this approach to fourteen alcohols and four amines illustrates its scope and limitations. Copyright (C) 1996 Elsevier Science Ltd