(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

• The Biotransformation of Foreign Substrates by Tissue Cultures. I. The Hydroxylation of Linalool and Its Related Compounds with the Suspension Cells of<i>Nicotiana tabacum</i>
  作者：Toshifumi Hirata、Tadashi Aoki、Yoshio Hirano、Takashi Ito、Takayuki Suga

  DOI：10.1246/bcsj.54.3527

  日期：1981.11

  It was found that the tissue cultures of Nicotiana tabacum “Bright Yellow” possess the ability to transform selectively the trans-methyl group in the 3-methyl-2-butenyl group of such foreign substrates as linalool and the related compounds into the hydroxymethyl group. Also, the cultures were found to have the ability to hydrolize the acetoxyl group of their acetates.

  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。
• 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.
• Direct, Biomimetic Synthesis of (+)-Artemone via a Stereoselective, Organocatalytic Cyclization
  作者：David Vosburg、Eric Nacsa、Brian Fielder、Shannon Wetzler、Veerasak Srisuknimit、Jonathan Litz、Mary Van Vleet、Kim Quach

  DOI：10.1055/s-0034-1380684

  日期：——

  Abstract We present a four-step synthesis of (+)-artemone from (–)-linalool, featuring iminium organocatalysis of a doubly diastereoselective conjugate addition reaction. The strategy follows a proposed biosynthetic pathway, rapidly generates stereochemical complexity, uses no protecting groups, and minimizes redox manipulations. We present a four-step synthesis of (+)-artemone from (–)-linalool, featuring

  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。