(S)-(-)-2,6-dimethyl-8-acetoxyoct-2-enal | 98169-01-8

• 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: (S)-(-)-2,6-dimethyl-8-acetoxyoct-2-enal
• 英文别名: (3S,6E)-3,7-Dimethyl-8-oxo-6-octenyl acetate；[(E,3S)-3,7-dimethyl-8-oxooct-6-enyl] acetate
• CAS: 98169-01-8
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: HEUSWAZSUJSVCG-OTXQMUPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2,6-dimethyl-8-acetoxyoct-2-enal 以44%的产率得到
  参考文献：
  名称：

  GRAMATICA, P.;MANITTO, P.;POLI, L., J. ORG. CHEM., 1985, 50, N 23, 4625-4628

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(-)-β-香茅醇 在 吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 selenium(IV) oxide 作用下， 以 甲苯 为溶剂， 反应 120.0h， 生成 (S)-(-)-2,6-dimethyl-8-acetoxyoct-2-enal
  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

文献信息

• Chiral synthetic intermediates via asymmetric hydrogenation of .alpha.-methyl-.alpha.,.beta.-unsaturated aldehydes by bakers' yeast
  作者：Paola Gramatica、Paolo Manitto、Laura Poli

  DOI：10.1021/jo00223a038

  日期：1985.11