10-Oxoneral | 80054-41-7

• 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: 10-Oxoneral
• 英文别名: (2Z,6E)-8-oxoneral；(2Z,6E)-3,7-dimethyl-2,6-octadiene-1,8-dial；8-oxoneral；(2E,6Z)-2,6-Dimethyl-2,6-octadienedial；(2E,6Z)-2,6-dimethylocta-2,6-dienedial
• CAS: 80054-41-7
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: GRHWFPUCRVCMRY-SCWCTGRGSA-N

物化性质

• 沸点：
  307.7±30.0 °C(Predicted)
• 密度：
  0.949±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  橙花醇 在 吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 selenium(IV) oxide 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 169.0h， 生成 10-Oxoneral
  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

• Resolution of an Iridoid Synthon, Gastrolactol, by Means of Dynamic Acetylation and Lipase-Catalyzed Alcoholysis
  作者：Ellen M. Santangelo、Didier Rotticci、Ilme Liblikas、Torbjörn Norin、C. Rikard Unelius

  DOI：10.1021/jo015592y

  日期：2001.8.1

  A short synthetic route to asymmetric iridoids was developed. The three key steps were an intramolecular [4 + 2] cycloaddition reaction of an enamine derivative of 8-oxocitral (2), a dynamic acetylation, and an enzymatic resolution of the gastrolactyl acetates 5a and 5b, iridoids with three stereocenters. Some regio- and stereoselective heterogeneous catalytic hydrogenations of double bonds in iridoid

  开发了合成不对称虹彩的简短途径。这三个关键步骤是8-氧肟酸酯（2）的烯胺衍生物的分子内[4 + 2]环加成反应，动态乙酰化以及乙酸甘油酯乙酸酯5a和5b的酶解，具有三个立体中心的虹彩化合物。讨论了环烯基配体中双键的一些区域和立体选择性非均相催化加氢反应。
• Battersby, Alan R.; Thompson, Mervyn; Gluesenkamp, Karl-Heinz, Chemische Berichte, 1981, vol. 114, # 10, p. 3430 - 3438
  作者：Battersby, Alan R.、Thompson, Mervyn、Gluesenkamp, Karl-Heinz、Tietze, Lutz-F.

  DOI：——

  日期：——