(R)-(+)-10-hydroxycitronellol | 82467-70-7

• 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: (R)-(+)-10-hydroxycitronellol
• 英文别名: (E,6R)-2,6-dimethyloct-2-ene-1,8-diol
• CAS: 82467-70-7
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: FZBXHGXRUNRMTQ-RAJVOEEQSA-N

物化性质

• 沸点：
  275.6±28.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (R)-(+)-6-acetoxy-4-methylhexanal 在 aluminium hydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 (R)-(+)-10-hydroxycitronellol
  参考文献：
  名称：

  Studies on monoterpene glucosides and related natural products. XLV. Synthesis of 13C-labeled acyclic monoterpenes for studies on the mechanism of the iridane skeleton formation in the biosynthesis of iridoid glucosides.

  摘要：

  在研究从无环单萜生成环戊烷环的生物合成途径中，我们合成了以下13C标记的无环单萜系列前体:[9-13C]-和[4-13C]-10-羟基香茅醇(9)、[2-13C]-9, 10-二羟基香茅醇(10)、(R)-(+)-和(S)-(-)-[9-13C]-10-羟基香茅醇((R)-(+)-和(S)-(-)-8)、(R)-(+)-和(S)-(-)-[8-13C]-9, 10-二羟基香茅醇((R)-(+)-和(S)-(-)-11)。

  DOI：

  10.1248/cpb.30.927

文献信息

• The aphid sex pheromone cyclopentanoids: Synthesis in the elucidation of structure and biosynthetic pathways
  作者：Glenn W. Dawson、John A. Pickett、Diane W.M. Smiley

  DOI：10.1016/0968-0896(96)00012-0

  日期：1996.3

  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