4-prenyl-3,5,3′,4′-tetrahydroxy-(E)-stilbene | 1028254-67-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-prenyl-3,5,3′,4′-tetrahydroxy-(E)-stilbene
• 英文别名: trans-arachidin-1；4-C-prenyl piceatannol；5-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
• CAS: 1028254-67-2
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: QWYZAQGMPWBQTL-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-prenyl-3,5,3′,4′-tetrakis(methoxymethoxy)-(E)-stilbene 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以50%的产率得到4-prenyl-3,5,3′,4′-tetrahydroxy-(E)-stilbene
  参考文献：
  名称：

  Stilbenes as κ-Selective, Non-nitrogenous Opioid Receptor Antagonists

  摘要：

  The natural stilbene pawhuskin A has been shown to function as an opioid receptor antagonist, with preferential binding to the kappa receptor. This finding encouraged assembly of a set of analogues to probe the importance of key structural features. Assays on these compounds determined that one (compound 29) shows potent opioid receptor binding activity and significantly improved selectivity for the kappa receptor. These studies begin to illuminate the structural features of these non-nitrogenous opioid, receptor antagonists that are required for activity.

  DOI：

  10.1021/np4009046

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• Hepatoprotective Activity and Mechanisms of Prenylated Stilbenoids
  作者：Bailin Li、Shengtao Bo、Zhili Sheng、Hong Zhu、Yueming Jiang、Bao Yang

  DOI：10.1021/acs.jafc.3c09515

  日期：2024.1.24
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
• Stilbenes as κ-Selective, Non-nitrogenous Opioid Receptor Antagonists
  作者：Alyssa M. Hartung、John A. Beutler、Hernán A. Navarro、David F. Wiemer、Jeffrey D. Neighbors

  DOI：10.1021/np4009046

  日期：2014.2.28

  The natural stilbene pawhuskin A has been shown to function as an opioid receptor antagonist, with preferential binding to the kappa receptor. This finding encouraged assembly of a set of analogues to probe the importance of key structural features. Assays on these compounds determined that one (compound 29) shows potent opioid receptor binding activity and significantly improved selectivity for the kappa receptor. These studies begin to illuminate the structural features of these non-nitrogenous opioid, receptor antagonists that are required for activity.