(2'E)-2-(3',7'-dimethylocta-2',6'-dienyl)-6-methyl-2,5-cyclohexadiene-1,4-dione | 81532-02-7

• 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: (2'E)-2-(3',7'-dimethylocta-2',6'-dienyl)-6-methyl-2,5-cyclohexadiene-1,4-dione
• 英文别名: 2-(3,7-Dimethylocta-2,6-dien-1-yl)-6-methylbenzo-1,4-quinone；2-[(2E)-3,7-dimethylocta-2,6-dienyl]-6-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 81532-02-7
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: VDDALGSXMJYSIM-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2'E)-2-(3',7'-dimethylocta-2',6'-dienyl)-6-methyl-2,5-cyclohexadiene-1,4-dione 以 吡啶 为溶剂， 反应 4.0h， 生成 atractylochromene
  参考文献：
  名称：

  Powerful antioxidative agents based on garcinoic acid from Garcinia kola

  摘要：

  Investigation on the structure-antioxidative activity relationships of derivatives based on garcinoic acid from Garcinia kola (Guttiferae) led to discovery of a powerful antioxidative agent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00428-x
• 作为产物：
  描述：

  1-((E)-3,7-Dimethyl-octa-2,6-dienyl)-2,5-bis-methoxymethoxy-3-methyl-benzene 在 盐酸 、 manganese(IV) oxide 作用下， 以 甲醇 、 氯仿 、 苯 为溶剂， 反应 1.5h， 生成 (2'E)-2-(3',7'-dimethylocta-2',6'-dienyl)-6-methyl-2,5-cyclohexadiene-1,4-dione
  参考文献：
  名称：

  Powerful antioxidative agents based on garcinoic acid from Garcinia kola

  摘要：

  Investigation on the structure-antioxidative activity relationships of derivatives based on garcinoic acid from Garcinia kola (Guttiferae) led to discovery of a powerful antioxidative agent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00428-x

文献信息

• Isoprenoid dihydroquinones from a brown alga, Cystophora sp.
  作者：Robert J. Capon、Emilio L. Ghisalberti、Phillip R. Jefferies

  DOI：10.1016/0031-9422(81)83108-1

  日期：1981.1

  Abstract The lipids-soluble extract of the brown alga Cystophora sp. has yielded three new derivatives of geranyltoluquinol.

  摘要 褐藻 Cystophora sp. 的脂溶性提取物。已经产生了香叶基甲苯酚的三种新衍生物。
• Total Synthesis of Atrachinenins A and B
  作者：Sarah A. French、Christopher J. Sumby、David M. Huang、Jonathan H. George

  DOI：10.1021/jacs.2c09978

  日期：2022.12.21

  Inspired by a new biosynthetic hypothesis, we report a biomimetic total synthesis of atrachinenins A and B that explains their racemic nature. The synthesis exploits an intermolecular Diels–Alder reaction between a quinone meroterpenoid and E-β-ocimene, followed by intramolecular (3 + 2) cycloaddition and a late-stage aerobic oxidation. Divergent transformations of a simple model system gave several

  受新的生物合成假设的启发，我们报告了 atrachinenins A 和 B 的仿生全合成，这解释了它们的外消旋性质。该合成利用了醌类萜类化合物和E -β-罗勒烯之间的分子间 Diels-Alder 反应，然后是分子内 (3 + 2) 环加成和后期有氧氧化。一个简单模型系统的发散转变给出了几个复杂的多环支架，同时也暗示了 atrachinenin C 的结构修正。
• 5-Lipoxygenase and Cyclooxygenase-1 Inhibitory Active Compounds from <i>Atractylodes lancea</i>
  作者：Marion Resch、Alois Steigel、Zhong-liang Chen、Rudolf Bauer

  DOI：10.1021/np970430b

  日期：1998.3.1

  Lipophilic extracts of Atractylodes lancea rhizomes exhibited potent inhibitory activities in 5-lipoxygenase [IC50 (5-LOX) = 2.9 mu g/mL (n-hexane extract)] and cyclooxygenase-1 [IC50 (COX-1) = 30.5 mu g/mL (n-hexane extract)] enzymatic assays. Bioactivity-guided fractionation of the n-hexane extract led to the isolation of a new compound atractylochromene (1), a potent inhibitor in both test systems [IC50 (5-LOX) = 0.6 mu M, IC50 (COX-1) = 3.3 mu M] Also obtained was 2-[(2E)-3,7-dimethyl-2,6-octadienyl]-6-methyl-2,5-cyclohexadiene-1,4-dione (2), which showed a selective inhibitory activity against 5-LOX [IC50 (5-LOX) 0.2 mu M, IC50 (COX-1) 64.3 mu M]. The sesquiterpene atractylon (3) and the coumarin osthol (4) turned out to be moderate but selective 5-lipoxygenase inhibitors. Atractylenolides I (5), II (6), and III (7) showed no significant inhibitory effects for either enzyme. Structures were established by spectral data interpretation.

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