6-allyl-2,3-dimethoxyphenol | 450357-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-allyl-2,3-dimethoxyphenol
• 英文别名: 2,3-Dimethoxy-6-prop-2-enylphenol
• CAS: 450357-58-1
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: KJYCPOBHNSZMJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-allyl-2,3-dimethoxyphenol 在 氢氧化钾 、 sodium hydroxide 作用下， 生成 2-ethoxy-3,4-dimethoxy-1-propenyl-benzene
  参考文献：
  名称：

  99.肉豆蔻苷的合成

  摘要：

  DOI：

  10.1039/jr9490000436
• 作为产物：
  描述：

  5,6,6-trimethoxycyclohexa-2,4-dienone 在 二氯乙基铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 6-allyl-2,3-dimethoxyphenol
  参考文献：
  名称：

  Complete π-Facial Diastereoselectivity in Diels−Alder Reactions of Dissymmetric 2,4-Cyclohexadienones

  摘要：

  [GRAPHIC]The studies in the Diels-Alder reactions of 5-methoxy-masked o-benzoquinone (1a, R = OMe) and simple dissymmetric 2,4-cyclohexadienones 1b-e with methyl vinyl ketone, styrene, and benzyl vinyl ether are described. The dienones 1b-e reacted with dienophiles to form syn adducts (dienophile approach is syn to allylic methoxy group) exclusively.

  DOI：

  10.1021/ol020087o

文献信息

• Selective Claisen rearrangement and iodination for the synthesis of polyoxygenated allyl phenol derivatives
  作者：Antonella Bochicchio、Rossella Cefola、Sabine Choppin、Françoise Colobert、Maria Antonietta Di Noia、Maria Funicello、Gilles Hanquet、Isabella Pisano、Simona Todisco、Lucia Chiummiento

  DOI：10.1016/j.tetlet.2016.07.079

  日期：2016.9

  Allyl aryl ethers and allyl phenol derivatives were prepared starting from commercial or synthetized phenols. Either Williamson reaction or Et2AlCl catalyzed Claisen rearrangement was performed to obtain the polyoxygenated molecules. The pivotal allyl phenols were then modified by methylation, iodocyclization or electrophilic aromatic iodination to afford the polyoxygenated derivatives in good to excellent

  从商业或合成的苯酚开始制备烯丙基芳基醚和烯丙基苯酚衍生物。进行威廉姆森反应或Et 2 AlCl催化的克莱森重排以获得多加氧分子。然后通过甲基化，碘环化或亲电子碘化碘化对枢轴烯丙基苯酚进行改性，从而以良好或优异的收率得到多氧化衍生物。此外，还研究了它们对革兰氏阳性和革兰氏阴性细菌的抗菌性能。
• Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid
  作者：A. Bochicchio、L. Schiavo、L. Chiummiento、P. Lupattelli、M. Funicello、G. Hanquet、S. Choppin、F. Colobert

  DOI：10.1039/c8ob02052c

  日期：——

  myricanol in 9 steps and 4.9% overall yield starting from commercially available 2,3-dimethoxyphenol and methyl 3-(4-benzyloxyphenyl)propanoate. The key steps are a cross-metathesis to obtain a linear diarylheptanoid intermediate and a Suzuki–Miyaura domino reaction to generate the challenging macrocycle.

  据报道，杨梅醇的一种成分杨梅醇1可以降低微管相关蛋白tau（MAPT）的水平，该蛋白tau的积累在某些神经退行性疾病（例如阿尔茨海默氏病（AD））中起着重要作用。本文中，我们描述了一种新的合成路线，该路线可从9步制备丁香油，总收率为4.9％，从商业上可获得的2,3-二甲氧基苯酚和3-（4-苄氧基苯基）丙酸甲酯开始。关键步骤是交叉复分解以获得线性二芳基庚烷中间体和Suzuki-Miyaura多米诺反应以生成具有挑战性的大环。
• Structure-activity relationships of phenylpropanoids as growth inhibitors of the green alga Selenastrum capricornutum
  作者：Marina Della Greca、Pietro Monaco、Antonino Pollio、Lucio Previtera

  DOI：10.1016/0031-9422(92)80425-e

  日期：1992.12
• Total synthesis of the antitumor antibiotic streptonigrin
  作者：Steven M. Weinreb、Fatima Z. Basha、Satoshi Hibino、Nazir A. Khatri、Deukjoon Kim、Walter E. Pye、Tai Teh Wu

  DOI：10.1021/ja00366a028

  日期：1982.1
• New synthesized polyoxygenated diarylheptanoids suppress lipopolysaccharide-induced neuroinflammation
  作者：Anna Santarsiero、Antonella Bochicchio、Maria Funicello、Paolo Lupattelli、Sabine Choppin、Françoise Colobert、Gilles Hanquet、Lucie Schiavo、Paolo Convertini、Lucia Chiummiento、Vittoria Infantino

  DOI：10.1016/j.bbrc.2020.06.122

  日期：2020.9

  In neurodegenerative diseases, such as Alzheimer's disease, Huntington's disease, Parkinson's disease and multiple sclerosis, neuroinflammation induced by the microglial activation plays a crucial role. In effort to develop effective anti-neuroinflammatory compounds, different new linear polyoxygenated diarylheptanoids were synthesized. In LPS-triggered BV-2 microglial cells their ability to reduce the concentration of IL-6 and TNF-alpha pro-inflammatory cytokines was evaluated. Moreover, their effect on NF-kappa B and ATP citrate lyase (ACLY), a recently emerged target of metabolic reprogramming in inflammation, was assessed. Finally, we turned our attention to inflammatory mediators derived from the cleavage of citrate catalyzed by ACLY: prostaglandin E-2, nitric oxide and reactive oxygen species. All compounds showed null or minimal cytotoxicity; most of them had a great anti-neuroinflammatory activity. Diarylheptanoids 6b and 6c, bearing a halide atom and benzyl ether protective groups, exhibited the best effect since they blocked the secretion of all inflammatory mediators analyzed and reduced NF-kB and ACLY protein levels. (c) 2020 Elsevier Inc. All rights reserved.