5-{6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-3-yl}benzene-1,3-diol | 129170-22-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-{6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-3-yl}benzene-1,3-diol
• 英文别名: (+)-ε-viniferin；(-)-ε-viniferin；5-[(2S,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
• CAS: 129170-22-5
• 化学式: C₂₈H₂₂O₆
• 分子量: 454.479
• InChiKey: FQWLMRXWKZGLFI-BQYFGGCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C储存

制备方法与用途

Description: This natural product is derived from plant sources and has been studied for its effects on melanin production in melanocyte cultures.

反应信息

• 作为反应物：
  描述：

  5-{6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-3-yl}benzene-1,3-diol 在 silver(I) acetate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以40%的产率得到vitisin B
  参考文献：
  名称：

  Regioselective Oxidative Coupling of 4-Hydroxystilbenes:  Synthesis of Resveratrol and ε-Viniferin (E)-Dehydrodimers

  摘要：

  Treatment of 5-[2-(4-hydroxyphenyl)vinyl]benzene-1,3-diol (resveratrol) with an equimolar amount of silver(I) acetate in dry MeOH at 50 degreesC for I h followed by chromatographic purification with a short silica gel column allowed the isolation of its (E)-dehydrodimer, 5-{5-[2-(3,5-dihydroxyphenyl)vinyl]-2-(4-hydroxyphenyl)-2,3-dihydrobenzofuran-3-yl}benzene-1, 3-diol, as a racemic mixture in high yield. The present method was applicable to the oxidative dimerization of 4-hydroxystilbenes such as trans-styrylphenol and 5-{6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-3-yl}benzene-1,3-diol (epsilon-viniferin) leading to the corresponding 2-(4-hydroxyphenyl)-2,3-dihydrobenzofurans possessing various types of biological activities.

  DOI：

  10.1021/jo035791c
• 作为产物：
  描述：

  白藜芦醇 在 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 5-{6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-3-yl}benzene-1,3-diol
  参考文献：
  名称：

  超高效液相色谱/电喷雾电离四极杆飞行时间质谱法研究红酒中的单体和低聚类酒类类胡萝卜素

  摘要：

  Stilbenoids是植物的次生代谢产物，负责保护多种植物物种，包括葡萄藤免受细菌和真菌感染。红酒已被证明是人类饮食中这些化合物的主要来源，它们在健康方面具有一系列好处。这项研究提供了红酒中存在的类胡萝卜素的完整信息，可检测出41种类胡萝卜素化合物，其中23种从未在红酒中被发现。

  DOI：

  10.1002/rcm.6636

文献信息

• Total Synthesis of Viniferifuran, Resveratrol-Piceatannol Hybrid, Anigopreissin A and Analogues - Investigation of Demethylation Strategies
  作者：Duc Duy Vo、Mikael Elofsson

  DOI：10.1002/adsc.201601089

  日期：2016.12.22

  constitute a valuable source of unique compounds with diverse biological activities. In this report we investigate demethylation strategies to minimize formation of cyclized and dimerized products during the synthesis of viniferifuran and analogues. We found that boron trichloride/tetra-n-butylammonium iodide (BCl3/TBAI) is typically more effective than boron tribromide (BBr3). Based on these findings

  基于白藜芦醇的天然产物是具有多种生物活性的独特化合物的宝贵来源。在本报告中，我们研究了去甲基化策略，以最大限度地减少 viniferifuran 及其类似物合成过程中环化和二聚产物的形成。我们发现三氯化硼/四正丁基碘化铵 (BCl3/TBAI) 通常比三溴化硼 (BBr3) 更有效。基于这些发现，我们首次合成了脱氢-δ-葡萄素、白藜芦醇-白皮杉醇混合物和 anigopreissin A。此外，我们还开发了一种短而有效的葡萄呋喃路线，通过六个步骤获得了 13% 的产率。
• Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological Activity and Molecular Modelling Evidence for Cooperativity between Viniferin Enantiomers
  作者：Luce M. Mattio、Mauro Marengo、Chiara Parravicini、Ivano Eberini、Sabrina Dallavalle、Francesco Bonomi、Stefania Iametti、Andrea Pinto

  DOI：10.3390/molecules24183225

  日期：——

  To improve the current understanding of the role of stilbenoids in the management of diabetes, the inhibition of the pancreatic α-amylase by resveratrol derivatives was investigated. To approach in a systematic way, the mechanistic and structural aspects of the interaction, potential bioactive agents were prepared as single molecules, that were used for the biological evaluation of the determinants

  为了提高目前对二苯乙烯类化合物在糖尿病治疗中作用的认识，研究了白藜芦醇衍生物对胰腺α-淀粉酶的抑制作用。为了系统地研究相互作用的机制和结构方面，潜在的生物活性剂被制备为单分子，用于抑制性结合决定因素的生物学评估。一些二聚二苯乙烯类化合物，特别是葡萄苷异构体，被发现在抑制胰腺 α-淀粉酶方面比参比药物阿卡波糖更好。在相同的总浓度下，葡萄素的外消旋混合物是比各自分离的纯对映体更有效的抑制剂，并且表现出单独对映体未观察到的协同效应。分子对接分析为测量的抑制能力和观察到的协同效应提供了基于热力学的原理。事实上，发现α-淀粉酶表面上额外配体的结合降低了与酶活性位点结合的抑制剂的解离常数，从而为观察到的抑制协同作用提供了机制原理。
• Tf2O-catalyzed Friedel–Crafts alkylation to synthesize dibenzo[a,d]cycloheptene cores and application in the total synthesis of Diptoindonesin D, Pauciflorial F, and (±)-Ampelopsin B
  作者：Gang-Wei Wang、Hong-Li Wang、David A. Capretto、Qi Han、Rong-Bin Hu、Shang-Dong Yang

  DOI：10.1016/j.tet.2012.03.073

  日期：2012.7

  By using Tf2O as a catalyst, we have developed a protocol for the preparation of various dibenzo[a,d]cycloheptene cores via Friedel–Crafts alkylation. Using this method as the key step, we also present concise and useful routes to synthesize the natural products Diptoindonesin D, Pauciflorial F, and (±)-Ampelopsin B. Notably, this process exhibited following very attractive features: (i) the process

  通过使用Tf 2 O作为催化剂，我们已经开发了通过Friedel-Crafts烷基化反应制备各种二苯并[ a，d ]环庚烯核的方案。使用此方法作为关键步骤，我们还提供了简洁实用的途径来合成天然产物Diptoindonesin D，洋紫苏F和（±）-AmpelopsinB。值得注意的是，该过程具有以下非常吸引人的特征：不含金属，仅使用催化量的Tf 2 O，并且（ii）该方法简单且环保，避免使用过量的碱，氧化剂或其他添加剂。
• COMPOSITIONS COMPRISING STILBENE POLYPHENOL DERIVATIVES AND USE THEREOF FOR COMBATING THE AGEING OF LIVING ORGANISMS AND DISEASES AFFECTING SAME
  申请人：Vercauteren Joseph

  公开号：US20100310615A1

  公开（公告）日：2010-12-09

  The invention relates to compositions comprising pholyphenol derivatives, characterised in that said polyphenols contain monomers, oligomers or polymers with units having formula (I), said units being characterised by the simultaneous presence of a resorcinol nucleus (nucleus A) and a para-phenol nucleus (nucleus B) which are interconnected by a carbon bond C, said derivatives being over-activated, in respect of the nucleophilic power thereof, by alkylation of at least one phenol function of each constituent monomer unit and stabilised by sterification by mixtures of fatty acids in proportions reflecting those of vegetable oils formed mainly by unsaturated fatty acids of all of the other phenol functions. The invention is suitable for use in cosmetics, dietetics and therapeutics.

  本发明涉及包含多酚衍生物的组合物，其特征在于该多酚含有单体、寡聚体或聚合物，其中单位具有式(I)，该单位的特征是鄄醌核（核A）和对位酚核（核B）同时存在，并由碳键C相互连接，该衍生物通过烷基化至少一个单体单位的酚功能而在其亲核功率方面过度活化，并通过脂肪酸混合物的酯化稳定，其中混合物的比例反映了主要由不饱和脂肪酸形成的植物油的所有其他酚功能。本发明适用于化妆品、饮食和治疗。
• Oxidative cross-coupling approach to the biomimetic synthesis of the heterodimers of resveratrol and isorhapontigenin
  作者：Hongpeng Li、Lu Ran、Meijie Liu、Tian Lei、Xiaodong Kang、Wenling Li

  DOI：10.1016/j.tetlet.2020.152239

  日期：2020.8

  The regioselective oxidative cross-coupling reactions of two different stilbene precursors catalyzed by FeCl3 or horseradish peroxidase-H2O2 in acetone solvent produced three dihydrobenzofuran-type heterodimers. The reductive debrominations of these cross-coupled dimers synthesized two heterodimers of resveratrol and isorhapontigenin, an analogue of (±)-scirpusin A and (±)-gnetuhainin Q.

  FeCl 3或辣根过氧化物酶-H 2 O 2在丙酮溶剂中催化的两种不同的二苯乙烯前体的区域选择性氧化交叉偶联反应产生了三种二氢苯并呋喃型异二聚体。这些交叉偶联的二聚体的还原脱溴反应合成了白藜芦醇和异皂甙元的两个异二聚体，这是（±）-scirpusin A和（±）-gnetuhainin Q的类似物。