(2E)-8-hydroxy-2,6-dimethyl-2-octenal | 194092-52-9

• 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: (2E)-8-hydroxy-2,6-dimethyl-2-octenal
• 英文别名: (E)-8-hydroxy-2,6-dimethyl-oct-2-enal；(+/-)-trans-8-oxo-citronellol；(E)-8-hydroxy-2,6-dimethyloct-2-enal
• CAS: 194092-52-9
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: DQQMOUVABPRNEO-BJMVGYQFSA-N

物化性质

• 沸点：
  279.0±23.0 °C(Predicted)
• 密度：
  0.934±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-8-hydroxy-2,6-dimethyl-2-octenal 在 platinum(IV) oxide 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 9.5h， 生成 2,6-二甲基辛烷-1,8-二醇
  参考文献：
  名称：

  Chiral synthetic intermediates via asymmetric hydrogenation of .alpha.-methyl-.alpha.,.beta.-unsaturated aldehydes by bakers' yeast

  摘要：

  DOI：

  10.1021/jo00223a038
• 作为产物：
  描述：

  乙酸香茅酯 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 121.0h， 生成 (2E)-8-hydroxy-2,6-dimethyl-2-octenal
  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

• (2<i>E</i>,6<i>R</i>)-8-Hydroxy-2,6-dimethyl-2-octenoic Acid, a Novel<i>Anti</i>-osteoporotic Monoterpene, Isolated from<i>Cistanche salsa</i>
  作者：Kohji YAMAGUCHI、Chikara SHINOHARA、Sachiko KOJIMA、Mikiko SODEOKA、Tomoko TSUJI

  DOI：10.1271/bbb.63.731

  日期：1999.1

  (2E,6R)-8-Hydroxy-2,6-dimethyl-2-octenoic acid [(R)-HDOA], a novel monoterpene from Cistanche salsa, a Chinese herb, was found to be an anti-osteoporotic compound. The extract of Cistanche salsa significantly suppressed the bone weight loss in ovariectomized mice, a postmenopausal osteoporosis model. The active substance was then purified by using this osteoporotic model and the chemical structure was determined. The active compound from Cistanche salsa, (R)-HDOA, suppressed the decrease of bone weight and the mechanical strength in the ovariectomized mice. Furthermore, (R)- and (S)-HDOA were synthesized and the activity of each was evaluated. (R)-HDOA suppressed the bone weight loss, although (S)-HDOA did not showed any activity.

  (2E,6R)-8-羟基-2,6-二甲基-2-辛烯酸[(R)-HDOA]是从中国草药肉苁蓉中发现的一种新型单萜化合物，具有抗骨质疏松特性。肉苁蓉提取物显著抑制了卵巢切除小鼠（一种绝经后骨质疏松模型）的骨重量损失。通过利用这一骨质疏松模型对该活性物质进行纯化，并确定了其化学结构。肉苁蓉中的活性化合物(R)-HDOA抑制了卵巢切除小鼠骨重量的减少和力学强度的下降。进一步合成了(R)-和(S)-HDOA，并对它们各自的活性进行了评估。(R)-HDOA抑制了骨重量损失，而(S)-HDOA未显示出任何活性。
• Selective Oxidation of Allylic Methyl Groups over a Solid Support under Microwave Irradiation†
  作者：Jasvinder Singh、Munisha Sharma、Govesdhan L. Kad、Balder R. Chhabra

  DOI：10.1039/a700758b

  日期：——

  SeO 2 /Bu t OOH adsorbed on SiO 2 is found to be a highly selective reagent for the oxidation of allylic methyl groups to trans-α,β-unsaturated aldehydes under microwave irradiation.

  发现吸附在 SiO 2 上的 SeO 2 /Bu t OOH 是一种高选择性试剂，用于在微波辐射下将烯丙基甲基氧化为反式-α,β-不饱和醛。
• Biosynthesis of loganin and the indole alkaloids from hydroxygeraniol–hydroxynerol
  作者：A. R. Battersby、S. H. Brown、T. G. Payne

  DOI：10.1039/c29700000827

  日期：——

  Tracer experiments on Vinca rosea indicate that the conversion of geraniol and nerol into loganin and the indole alkaloids involves 10-hydroxylation as the primary step.

  在长春花上的示踪剂实验表明，香叶醇和神经醇转化为loganin和吲哚生物碱涉及的主要步骤是10-羟基化。
• Oxidation of alcohols with tert-butyl hydroperoxide and diaryl diselenide
  作者：Isao Kuwajima、Makoto Shimizu、Hirokazu Urabe

  DOI：10.1021/jo00344a017

  日期：1982.2
• Efficient Role of Ionic Liquid (bmim)HSO₄ as Novel Catalyst for Monotetrahydropyranylation of Diols and Tetrahydropyranylation of Alcohols
  作者：Jasvinder Singh、Neeraj Gupta、Goverdhan L. Kad、Jasamrit Kaur

  DOI：10.1080/00397910600770839

  日期：2006.9.1