pallidol

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: pallidol
• 英文别名: (4bS,5S,9bS,10S)-5,10-bis(4-hydroxyphenyl)-4b,5,9b,10-tetrahydroindeno[2,1-a]indene-1,3,6,8-tetrol
• 化学式: C₂₈H₂₂O₆
• 分子量: 454.479
• InChiKey: YNVJOQCPHWKWSO-KBJUPQRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  121
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 三氟甲磺酸 作用下， 反应 0.5h， 以85%的产率得到pallidol
  参考文献：
  名称：

  Synthesis of diverse oligostilbenes from FeCl 3 -mediated oxidation of protected resveratrol

  摘要：

  FeCl3-catalyzed oxidative coupling reactions of protected resveratrol in the different solvents directly constructed three distinct dimeric skeletons, which were converted into several oligostilbenes through the respective global deprotections. The solvent effects on the structures of coupling products and reaction pathways involved were briefly discussed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.028

文献信息

• Total Synthesis of Resveratrol-Based Natural Products Using a Palladium-Catalyzed Decarboxylative Arylation and an Oxidative Heck Reaction
  作者：Felix Klotter、Armido Studer

  DOI：10.1002/anie.201310676

  日期：2014.2.24

  Controlled access to resveratrol‐based natural products is offered by a novel, modular concept. A common building block readily available on a large scale serves as the starting material for the introduction of structurally important aryl groups by a Pd‐catalyzed decarboxylative arylation and an oxidative Heck reaction with good yields and high stereoselectivity. The modular approach is convincingly

  新颖的模块化概念提供了对基于白藜芦醇的天然产品的可控使用权。大规模容易获得的通用构件是通过Pd催化的脱羧芳基化和氧化Heck反应以良好的收率和高的立体选择性引入结构上重要的芳基的起始材料。三种基于外消旋白藜芦醇的天然产物（四rangularin A，ampelopsin D和pallidol）的成功合成令人信服地证明了该模块化方法。
• 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。
• A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities
  作者：Bryan S. Matsuura、Mitchell H. Keylor、Bo Li、YuXuan Lin、Shelby Allison、Derek A. Pratt、Corey R. J. Stephenson

  DOI：10.1002/anie.201409773

  日期：2015.3.16

  An efficient synthetic route to the resveratrol oligomers quadrangularin A and pallidol is reported. It features a scalable biomimetic oxidative dimerization that proceeds in excellent yield and with complete regioselectivity. A systematic evaluation of the natural products and their synthetic precursors as radical‐trapping antioxidants has revealed that, contrary to popular belief, this mode of action

  据报道，合成白藜芦醇寡聚体quadrangularin A和pallidol的有效途径。它具有可扩展的仿生氧化二聚作用，能以优异的收率和完全的区域选择性进行。对天然产物及其合成前体作为捕获自由基的抗氧化剂的系统评价表明，与普遍的看法相反，这种作用方式不太可能解释其观察到的生物活性。
• Sulfoxide-Based Enantioselective Nazarov Cyclization: Divergent Syntheses of (+)-Isopaucifloral F, (+)-Quadrangularin A, and (+)-Pallidol
  作者：Mei-Lin Tang、Peng Peng、Zheng-Yu Liu、Jian Zhang、Jian-Ming Yu、Xun Sun

  DOI：10.1002/chem.201603664

  日期：2016.10.4

  The synthesis of enantiomerically pure 3‐aryl substituted indanones is developed using an enantioselective sulfoxide‐based Knoevenagel condensation/Nazarov cyclization procedure. After the reductive desulfonation of the methyl para‐tolyl sulfoxide‐containing chiral auxiliary under mild conditions, selected enantiomerically pure indanone is used for the divergent total syntheses of three resveratrol

  对映体纯的3-芳基取代的茚满酮的合成是使用基于对映选择性亚砜的Knoevenagel缩合/ Nazarov环化程序进行的。在温和的条件下对甲基对甲苯基亚砜的手性助剂进行还原脱硫后，所选对映体纯的茚满酮用于三种白藜芦醇天然产物（+）-异古风化的F，（+）-四环素A和（+）-pallidol。
• Investigation of monomeric and oligomeric wine stilbenoids in red wines by ultra-high-performance liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry
  作者：Ryan Moss、Qinyong Mao、Dennis Taylor、Cédric Saucier

  DOI：10.1002/rcm.6636

  日期：2013.8.30

  Stilbenoids are secondary plant metabolites responsible for the protection of multiple plant species including grape vine from bacterial and fungal infection. Red wine has been shown to be a major source of these compounds in the human diet, where they display an array of health benefits. Providing a more complete profile of the stilbenoids present in red wine, this study detects 41 stilbenoid compounds

  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。