(R)-8-oxolinalool | 61476-71-9

• 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: (R)-8-oxolinalool
• 英文别名: 8-oxolinalool；(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienal
• CAS: 61476-71-9
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: HRVZNWRZLYDLBU-ZKXNXJMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (R)-8-oxolinalool 在 二氯二茂钛 、 C₂₀H₂₇NOSi 、 锌 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.0h， 生成 4,4-dimethyl-2-(5-methyl-5-vinyltetrahydrofuran-2-yl)hex-5-en-3-ol
  参考文献：
  名称：

  通过立体选择性有机催化环化直接仿生合成（+）-青蒿酮

  摘要：

  摘要 我们提出了从（-）-芳樟醇合成（+）-青蒿酮的四步合成法，其特征在于双非对映选择性共轭加成反应的亚胺基有机催化。该策略遵循拟议的生物合成途径，快速产生立体化学复杂性，不使用保护基，并最大程度地减少氧化还原操纵。 我们提出了从（-）-芳樟醇合成（+）-青蒿酮的四步合成法，其特征在于双非对映选择性共轭加成反应的亚胺基有机催化。该策略遵循拟议的生物合成途径，快速产生立体化学复杂性，不使用保护基，并最大程度地减少氧化还原操纵。

  DOI：

  10.1055/s-0034-1380684
• 作为产物：
  描述：

  (R)-芳樟醇 在 manganese(IV) oxide 作用下， 以 四氯化碳 为溶剂， 反应 180.0h， 生成 (R)-8-oxolinalool
  参考文献：
  名称：

  The Biotransformation of Foreign Substrates by Tissue Cultures. I. The Hydroxylation of Linalool and Its Related Compounds with the Suspension Cells ofNicotiana tabacum

  摘要：

  研究发现，"亮黄 "烟草（Nicotiana tabacum）组织培养物具有将芳樟醇及相关化合物等外来底物的 3-甲基-2-丁烯基中的反式甲基选择性转化为羟甲基的能力。此外，还发现这些培养物具有水解其乙酸酯的乙酰氧基的能力。

  DOI：

  10.1246/bcsj.54.3527

文献信息

• Structure and Synthesis of a New Monoterpenoidal Carboxamide from the Seeds of the Thai Medicinal Plant Acacia concinna.
  作者：Toshikazu SEKINE、Nobuaki FUKASAWA、Fumio IKEGAMI、Kazuki SAITO、Yuichi FUJII、Isamu MURAKOSHI

  DOI：10.1248/cpb.45.148

  日期：——

  A new monoterpenoidal carboxamide, concinnamide (1), has been isolated from the seeds of a Thai medicinal plant, Acacia concinna DC. (Leguminosae). Its structure has been revised to (E)-2, 6-dimethyl-6-hydroxy-2, 7-octadienamide by detailed spectroscopic and synthetic studies, though it had been preliminarily assigned as a seven-membered lactam derivative by our previous work. (-)-Concinnamide, (-)-1, was synthesized from (-)-linalool (2) by stepwise oxidation, followed by amidation to confirm the structure. The inhibitory effects of 1 and related compounds on the arachidonate 5-lipoxygenase of RBL-1 cells are also described.

  从泰国药用植物 Acacia concinna DC 的种子中分离出一种新的单萜甲酰胺，即 concinnamide (1)。 （豆科）。尽管我们之前的工作初步将其确定为七元内酰胺衍生物，但通过详细的光谱和合成研究，其结构已被修改为(E)-2,6-二甲基-6-羟基-2,7-辛二烯酰胺。 (-)-肉桂酰胺，(-)-1，由(-)-芳樟醇(2)通过逐步氧化合成，然后酰胺化以确认结构。还描述了1和相关化合物对RBL-1细胞的花生四烯酸5-脂氧合酶的抑制作用。
• Chirality and biosynthesis of lilac compounds in Actinidia arguta flowers
  作者：A.J. Matich、B.J. Bunn、D.J. Comeskey、M.B. Hunt、D.D. Rowan

  DOI：10.1016/j.phytochem.2007.03.023

  日期：2007.7

  Biosynthesis of lilac compounds in 'Hortgem Tahi' kiwifruit (Actinidia arguta) flowers was investigated by treating inflorescences with d(5)-linalool. The incorporation of the deuterium label into 8-hydroxylinalool, 8-oxolinalool, the lilac aldehydes, alcohols, and alcohol epoxides was followed by GGMS and enantioselective GC-MS. Both (R)- and (S)-linalool were produced naturally by the flowers, but 8-hydroxylinalool, 8-oxolinalool, and the lilac aldehydes and alcohols occurred predominantly as the (S) and 5'(S)-diastereoisomers, respectively. The enantio selective step in the biosynthesis of the lilac aldehydes and alcohols was concluded to be the oxidation of linalool to (S)-8-hydroxylinalool. In contrast, the lilac alcohol epoxides had a 5'(R):(S) ratio, the same as for linalool, which suggests that either these compounds are not synthesised from the 5'(S)-configured lilac aldehydes and alcohols, or that if indeed they are, then it is by an enantioselective step that favours utilisation of the 5'(R)-configured compounds. (c) 2007 Elsevier Ltd. All rights reserved.