2-hydroxystilbene | 76425-88-2

• 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: 2-hydroxystilbene
• 英文别名: 3-hydroxystilbene；3-styrylphenol；3-(2-Phenylethenyl)phenol
• CAS: 76425-88-2
• 化学式: C₁₄H₁₂O
• mdl: MFCD00016459
• 分子量: 196.249
• InChiKey: XBHJTSIYYWRJFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-hydroxystilbene 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 生成 3-苯乙基酚
  参考文献：
  名称：

  Syntheses and in Vitro Antiplasmodial Activity of Aminoalkylated Chalcones and Analogues

  摘要：

  A series of readily synthesized and inexpensive aminoalkylated chalcones and diarylpropane analogues (1-55) were synthesized and tested against chloroquinone-sensitive (D10 and NF54) and -resistant (Dd2 and K1) strains of Plasmodium falciparum. Hydrogenation of the enone to a diarylpropane moiety increased antiplasmodial bioactivity significantly. The influence of the structure of the amine moiety, A-ring substituents, propyl vs ethyl linker, and chloride salt formation on further enhancing antiplasmodial activity was investigated. Several compounds have IC50 values similar to or better than chloroquine (CQ). The most active compound (26) had an IC50 value of 0.01 mu M. No signs of resistance were detected, as can be expected from compounds with structures unrelated to CQ and other currently used antimalarial drugs. Toxicity tests (in vitro CHO cell assay) gave high SI indices.

  DOI：

  10.1021/acs.jnatprod.5b00114
• 作为产物：
  描述：

  苯基膦酸二乙酯 在 potassium tert-butylate 、 吡啶盐酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-hydroxystilbene
  参考文献：
  名称：

  pH-switched HRP-catalyzed dimerization of resveratrol: a selective biomimetic synthesis

  摘要：

  本文介绍了一种以天然白藜芦醇单体为起始原料，选择性地、简洁地合成七种白藜芦醇二聚体的绿色仿生合成策略。通过简洁地调节环境 pH 值，所使用的辣根过氧化物酶（HRP）能以三种截然不同的模式发挥作用，并以相当高的选择性形成了五种二聚体。随后还合成了另外两种衍生物二聚体。

  DOI：

  10.1039/c2gc36288k

文献信息

• Heterogeneous Catalysis by Covalent Organic Frameworks (COF): Pd(OAc)₂@COF-300 in Cross-Coupling Reactions
  作者：Raoni S. B. Gonçalves、Alline B. V. de Oliveira、Haryadylla C. Sindra、Bráulio S. Archanjo、Martín E. Mendoza、Leonardo S. A. Carneiro、Camilla D. Buarque、Pierre M. Esteves

  DOI：10.1002/cctc.201500926

  日期：2016.2

  imine‐linked, crystalline, and microporous covalent organic framework, modified by coordination of Pd(OAc)2 to its walls, afforded a hybrid material, Pd(OAc)2@COF‐300, which was used as an efficient heterogeneous catalyst for cross‐coupling reactions. This material showed excellent catalytic activity for the phosphine‐free Suzuki–Miyaura, Heck, and Sonogashira cross‐coupling reactions with low palladium loadings

  COF-300是一种亚胺连接的，结晶的，微孔的共价有机骨架，通过将Pd（OAc）2与其壁配位而改性，从而提供了杂化材料Pd（OAc）2 @ COF-300，该材料用作用于交叉偶联反应的高效多相催化剂。该材料对钯含量低（0.1 mol％Pd）的无膦的Suzuki-Miyaura，Heck和Sonogashira交叉偶联反应显示出优异的催化活性。反应后催化剂的X射线光电子能谱分析表明，Pd II转化为Pd 0，并被捕集在COFs纳米孔中。高分辨率透射电子显微镜证实了这一点。此外，使用Pd（OAc）获得了可喜的结果2 @ COF‐300在连续流动条件下进行的Suzuki–Miyaura交叉偶联反应。
• Photolytic release of bioactive carboxylic acids from fused pyran conjugates
  作者：Rafaela Conceição、Graham Hungerford、Susana P.G. Costa、M. Sameiro T. Gonçalves

  DOI：10.1016/j.dyepig.2017.09.023

  日期：2018.1

  New ester cages bearing the coumarin (2H-benzopyran-2-one) skeleton with extended π-systems as phototriggers, for glycine and β-alanine, as models of carboxylic acid bifunctional molecules with biological relevance, were evaluated under photolysis conditions at 254, 300, 350 and 419 nm of irradiation in a RPR-100 photochemical reactor. The processes were followed by HPLC-UV detection and 1H NMR with

  在254的光解条件下，评估了带有香豆素（2 H-苯并吡喃-2-酮）骨架并具有扩展的π系统作为光触发的新酯笼，用于光触发的甘氨酸和β-丙氨酸作为具有生物相关性的羧酸双功能分子模型在RPR-100光化学反应器中照射300、350和419 nm。该过程之后进行HPLC-UV检测和1 H NMR，并收集动力学数据。结果表明，甘氨酸和β-丙氨酸的光解效率与共轭作用的增加扩展之间存在相关性，表明7-氨基香豆素在所有测试波长下均能提供最佳结果。 通过对时间分辨荧光行为的研究，还发现这些化合物表现出更复杂的荧光衰减动力学。这归因于共轭和非共轭香豆素种类的存在。
• Iron catalysis for the synthesis of ligands: Exploring the products of hydrophosphination as ligands in cross-coupling
  作者：Maialen Espinal-Viguri、Mary F. Mahon、Simon N.G. Tyler、Ruth L. Webster

  DOI：10.1016/j.tet.2016.11.058

  日期：2017.1

  Catalytic hydrophosphination is a useful technique for the synthesis of phosphines, however, the phosphine products have been little exploited as ligands in catalysis. We have selected three phosphines prepared by iron catalyzed hydrophosphination and used them as ligands in a series of cross-coupling reactions: Heck, Suzuki-Miyaura and Buchwald-Hartwig. Rather than limit the chemistry to simple cross-coupling

  催化氢磷酸化是合成膦的有用技术，但是，膦产物几乎没有被用作催化中的配体。我们选择了铁催化氢磷酸化制备的三种膦，并将它们用作一系列交叉偶联反应的配体：Heck，Suzuki-Miyaura和Buchwald-Hartwig。与其将化学反应局限于几乎可以保证在这些转化中表现良好的简单交叉偶联配偶体，还探索了从电子和/或立体角度来看具有挑战性的工业相关底物，以及包含多个杂原子的底物，以实现以下目的：测量这些膦配体的真正潜力。
• Convenient Access to <i>meta</i> -Substituted Phenols by Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling and Oxidation
  作者：Zi Wang、Arturo Orellana

  DOI：10.1002/chem.201702651

  日期：2017.8.22

  meta‐substituted phenols in which a single palladium catalyst accomplishes a Suzuki–Miyaura cross‐coupling between a β‐chlorocyclohexenone and an arylboronic acid, and oxidation of the resulting cyclohexenone to the corresponding phenol upon introduction of a terminal oxidant and electron transfer mediator. Notably, this method also allows ready access to ortho, meta‐disubstituted phenols, sterically congested

  我们报告了一种合成间位取代酚的新方法，其中单个钯催化剂完成了β-氯代环己烯酮和芳基硼酸之间的Suzuki-Miyaura交叉偶联，并在引入环戊烯酮之后将所得环己烯酮氧化为相应的苯酚末端氧化剂和电子转移介体。值得注意的是，这种方法还可以方便地使用邻位，间-二取代的苯酚，空间上拥挤的联芳基苯酚以及更高度取代的苯酚。
• Substituted CIS- and trans-stilbenes as therapeutic agents
  申请人：Vander Jagt David L.

  公开号：US20070249647A1

  公开（公告）日：2007-10-25

  The present invention relates to method(s) of treating a subject afflicted with cancer or a precancerous condition, an inflammatory disease or condition, and/or stroke or other ischemic disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans-stilbene.

  本发明涉及治疗患有癌症或癌前病变、炎症性疾病或病情以及中风或其他缺血性疾病或病情的方法，该方法包括向需要的受试者或患者施用含有一定治疗有效量的取代的顺式或反式-芪的组合物。