4,3’,4’-trimethoxystilbene | 263327-99-7

• 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: 4,3’,4’-trimethoxystilbene
• 英文别名: 4,3',4'-trimethoxystilbene；3,4,4'-trimethoxystilbene；trimethylresveratrol；1,2-dimethoxy-4-[2-(4-methoxyphenyl)ethenyl]benzene
• CAS: 263327-99-7
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: UDOKNDRSLIZXDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,3’,4’-trimethoxystilbene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到3,4,4'-trihydroxy-trans-stilbene
  参考文献：
  名称：

  Direct injection gas chromatographic mass spectrometric assay for trans-resveratrol

  摘要：

  We have developed a novel method to measure the concentration of the trihydroxystilbene trans-resveratrol suitable for the analysis of wine and other biological materials. Solid-phase extraction is carried out on a reversed-phase disposable C-18 cartridge with elution of trans-resveratrol by ethyl acetate. From the first 1 mL of the eluate collected, 1 mu L is injected directly into a gas chromatograph/mass spectrometer coupled through a DB-5 column. The molecular ion at a mass of 228 was quantitated by selective ion monitoring using as standard trans-resveratrol synthesized by a Wittig reaction. The method was linear up to 10 mg/L with a detection limit of 0.05 mg/L, which can be increased 10-fold if required. Recovery of added synthetic trans-resveratrol in wine ranged from 83 to 111% with a mean of 100%. Within-run precision was 5-7%. The method is faster and simpler than those previously published, which use organic-phase extraction, and yields higher values in wine presumably as a consequence of minimal loss during the solid-phase extraction. The trans-resveratrol. concentration of wine is stable when protected from light for at least 6 weeks at 4 degrees C and for at least 1 week at room temperature.

  DOI：

  10.1021/ac00094a017
• 作为产物：
  描述：

  (E)-3-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylic acid 在 copper(II) sulfate 作用下， 以 喹啉 为溶剂， 生成 4,3’,4’-trimethoxystilbene
  参考文献：
  名称：

  C8c–C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties

  摘要：

  Four enantiomerically pure monoseco-analogues, 5, 7, 9, and 11, of the phenanthroquinolizidine alkaloid julandine (1) and four of congener cryptopleurine (2), viz. compounds 6, 8, 10, and 12, have been prepared and subjected to preliminary biological evaluation. These analogues show dramatically reduced cytotoxicity compared with the parent system 2 but they are, nevertheless, potent anti-angiogenic agents. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.032

文献信息

• Carbene Based Palladium-catalyzed Mizoroki-Heck Reaction
  作者：VIVEK SRIVASTAVA

  DOI：10.13005/ojc/280444

  日期：2012.12.22

  Different perhydrobenzimidazolinium chloride salts were used as a ligand for PdcatalysedMizoroki-Heck reaction. The in situ generation of carbene is the attractive feature of this catalytic system. The corresponding Mizoroki-Heck products were obtained in good yield.

  不同的过氢苯并咪唑啉氯化物盐用作Pd催化的Mizoroki-Heck反应的配体。卡宾的原位生成是该催化系统的吸引人的特征。以高收率获得了相应的Mizoroki-Heck产品。
• One-Pot Two-Step Oxidative Cleavage of 1,2-Arylalkenes to Aryl Ketones Instead of Arylaldehydes in an Aqueous Medium: A Complementary Approach to Ozonolysis
  作者：Naina Sharma、Abhishek Sharma、Rakesh Kumar、Amit Shard、Arun K. Sinha

  DOI：10.1002/ejoc.201000672

  日期：2010.11

  A new approach has been developed for a one-pot and selective oxidative cleavage of aryl- and 1,2-diarylalkenes leading to one-carbon shorter aryl ketones; thereby, providing a complementary approach to classical ozonolysis. The methodology was applicable to diverse aromatic and polyaromaticarylalkenes bearing electron-donating or -withdrawing groups on the aromatic ring. The protocol also provided

  已开发出一种新方法，用于芳基和 1,2- 二芳基烯烃的一锅法选择性氧化裂解，产生一个碳的较短芳基酮；因此，为经典臭氧分解提供了一种补充方法。该方法适用于在芳环上带有给电子或吸电子基团的各种芳族和聚芳芳基烯烃。该方案还提供了一个有用的一锅氧化裂解-缩合序列，它可能在天然产物全合成中具有重要的应用。
• Stilbene synthesis through decarboxylative cross-coupling of substituted cinnamic acids with aryl halides
  作者：Nelly Rameau、Baptiste Russo、Stéphane Mangematin、Catherine Pinel、Laurent Djakovitch

  DOI：10.1016/j.apcata.2018.04.031

  日期：2018.6

  acid and aryl iodide derivatives was studied using both homogeneous and heterogeneous Pd-catalysts. It was demonstrated that simple Pd(OAc)2 can catalyze this reaction with useful to high yields when engaging ferulic acid whatever the nature of the aryl iodide. However, limitations were found when varying the nature of the cinnamic acid derivatives mainly due to low decarboxylation process. This could

  使用均相和非均相钯催化剂，研究了肉桂酸与芳基碘化物衍生物之间的钯催化的脱羧交叉偶联反应。已证明，无论芳基碘化物的性质如何，当与阿魏酸接合时，简单的Pd（OAc）2都可以高产率地催化该反应。然而，当改变肉桂酸衍生物的性质时，发现局限性主要是由于低脱羧过程。在某些情况下，可以通过添加Cu（OH）2 / 1,10-菲咯啉作为助催化剂来克服这一问题。在存在非均相催化剂的情况下，研究表明，Pd / C和自制的Pd / SiO 2催化剂均可提供较高的产品收率。然而，尽管活性较低，但已证明Pd / SiO由于具有较高的稳定性，因此2种催化剂可在至少4个循环中重复使用。
• Biomimetic Oxidative Dimerization of Anodically Generated Stilbene Radical Cations: Effect of Aromatic Substitution on Product Distribution and Reaction Pathways
  作者：Fong-Jiao Hong、Yun-Yee Low、Kam-Weng Chong、Noel F. Thomas、Toh-Seok Kam

  DOI：10.1021/jo500559r

  日期：2014.5.16

  type as a function of aromatic substitution. A reinvestigation of the electrochemical oxidation of 4,4′-dimethoxystilbene under various conditions was first carried out, and all products formed were fully characterized and quantitated. This was followed by a systematic investigation of the effect of aromatic substitution on the nature and distribution of the products. The aromatic substituents were found

  对1,2-二芳基烯烃的电化学氧化进行了系统的研究，重点是详细的产物研究和产物类型随芳族取代作用的变化。首先对各种条件下的4,4'-二甲氧基sti的电化学氧化进行了重新研究，并对形成的所有产物进行了充分表征和定量。随后，系统地研究了芳族取代对产品性质和分布的影响。发现芳族取代基分为三大类，即，其中芳族取代基的性质和位置产生与4,4'-二甲氧基苯乙烯基本相同的产物的底物，例如四芳基四氢呋喃，脱氢四氢萘和醛。 （p-MeO或p -NMe 2在一个环上，X在另一个环上，其中X = o -MeO或p-烷基，或m-或p -EWG；例如4-甲氧基-4'-三氟甲基sti）；那些产生茚满基（或四氢萘基）乙酰胺和脱氢四氢萘（或pallidols）（两个或一个被烷基取代的环，例如4,4'-二甲基1,2,5-二苯乙烯）的混合物的化合物；以及那些战略性放置施主基团（例如OMe和OH）的人导致了两性霉素F和pallidol型碳骨架（例如4
• Transformations of Ferric Chloride-Generated Stilbene Cation Radicals. The Effect of Aromatic Substitution and a Comparison with Anodic Oxidation
  作者：Fong-Jiao Hong、Kam-Weng Chong、Yun-Yee Low、Noel F. Thomas、Toh-Seok Kam

  DOI：10.1002/asia.201500488

  日期：2015.10

  FeCl3‐induced oxidation of 1,2‐diarylalkenes was carried out with the focus on the variation of product type as a function of aromatic substitution, as well as to compare the reactivity of stilbene cation radicals generated via FeIII oxidation with those generated by anodic oxidation. The aromatic substituents were found to fall into three main categories, namely those that give rise to tetralins and/or

  对FeCl 3诱导的1,2-二芳基烯烃的氧化进行了系统研究，重点是产物类型随芳族取代的变化，并比较了通过Fe III生成的二苯乙烯阳离子自由基的反应性阳极氧化产生的氧化。发现芳族取代基可分为三大类，即产生四氢萘和/或脱氢四氢萘的取代基，产生具有pallidol和ampelopsin F型碳骨架的产品，最后产生三聚体产物茚满的取代基。和脱氢四氢萘/四氢萘。后者是在一个环中具有对甲氧基取代基和对或间‐EWG（CF 3，NO 2，Cl，F）在另一个位置，与阳极氧化条件下相同苯乙烯的行为相比，代表了最突出的偏离。提出了合理化不同产物形成的反应途径。