(E)-4'-chloro-4-hydroxy-3-methoxystilbene

• 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: (E)-4'-chloro-4-hydroxy-3-methoxystilbene
• 英文别名: 4-chloro-4'-hydroxy-3'-methoxystilbene；4-hydroxy-3-methoxy-4'-chlorostilbene；4-[(E)-2-(4-chlorophenyl)ethenyl]-2-methoxyphenol
• 化学式: C₁₅H₁₃ClO₂
• 分子量: 260.72
• InChiKey: DWEKJLOYSNQSRK-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-Chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid 在 N-甲基咪唑 、 碳酸氢钠 作用下， 反应 0.33h， 以78%的产率得到(E)-4'-chloro-4-hydroxy-3-methoxystilbene
  参考文献：
  名称：

  Remarkable synergism in methylimidazole-promoted decarboxylation of substituted cinnamic acid derivatives in basic water medium under microwave irradiation: a clean synthesis of hydroxylated (E)-stilbenes

  摘要：

  A metal-free protocol for decarboxylation of substituted alpha-phenylcinnamic acid derivatives in aqueous media is developed, wherein a remarkable synergism between methylimidazole and aq NaHCO3 in polyethylene glycol under microwave furnished the corresponding para/ortho hydroxylated (E)-stilbenes in a mild and efficient manner. The critical role of water in facilitating the decarboxylation imparts an interesting facet to the synthetic utility of water mediated organic transformations. The developed protocol provides a clean alternative to the hitherto indispensable multistep approaches involving toxic quinoline and a copper salt combination as the common decarboxylating agent. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.046

文献信息

• ONE POT MULTICOMPONENT SYNTHESIS OF SOME NOVEL HYDROXY STILBENE DERIVATIVES WITH ALPHA, BETA-CARBONYL CONJUGATION UNDER MICROWAVE IRRADIATION
  申请人：Sharma Abhishek

  公开号：US20120165567A1

  公开（公告）日：2012-06-28

  The present invention provides a method for the preparation of some novel multiconjugated 2- or 4-hydroxy substituted stilbenes. The method provides one pot multicomponent approach wherein 3-4 step reaction sequences viz. condensation, decarboxylation and Heck coupling occur simultaneously which results in an enhanced yield of desired products and reduced reaction times

  本发明提供了一种制备一些新型多共轭2-或4-羟基取代的stilbenes的方法。该方法提供了一锅多组分方法，其中包括3-4步反应序列，即缩合、脱羧和Heck偶联同时发生，从而提高了所需产品的产量，减少了反应时间。
• Cu(acac)2-Catalyzed Synthesis of Functionalized Bis(arylmethyl)zinc Reagents and Their Olefination Reaction with Aromatic Aldehydes
  作者：Ying Fu、Xuemei Hu、Yaojuan Chen、Yanshou Yang、Hongxia Hou、Yulai Hu

  DOI：10.1055/s-0031-1289723

  日期：2012.4

  An efficient and facile copper(II) acetylacetonate catalyzed synthesis of functionalized bis(arylmethyl)zinc reagents from arylmethyl halides and their olefination reaction with aromatic aldehydes is reported. Aluminum trichloride was found to be the key ingredient in these reactions and (E)-stilbenes were obtained in high yields.

  报告了一种高效简便的乙酰丙酮酸铜(II)催化合成芳基甲基卤化物官能化双(芳基甲基)锌试剂及其与芳香醛的烯化反应。研究发现三氯化铝是这些反应的关键成分，并以高产率获得了(E)-二苯乙烯。
• An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction
  作者：Arun K. Sinha、Vinod Kumar、Abhishek Sharma、Anuj Sharma、Rakesh Kumar

  DOI：10.1016/j.tet.2007.08.034

  日期：2007.11

  selectivity has been developed through a modified Perkin reaction between benzaldehydes and phenylacetic acids bearing 4- or 2-hydroxy substitution at the aromatic ring, in the presence of piperidine–methylimidazole and polyethylene glycol under microwave irradiation. The observation of a simultaneous condensation–decarboxylation leading to the unusual formation of hydroxystilbenes in lieu of α-phenylcinnamic

  在存在哌啶-甲基咪唑和微波辐射下的聚乙二醇。观察到同时发生的缩合-脱羧反应会导致羟基苯乙烯的异常形成，以代替α-苯基肉桂酸，这揭示了经典珀金反应的一个有趣方面。所开发的方案为使用喹啉/铜盐形式的有毒脱羧剂的普遍方法提供了绿色替代方案，并且要求严格的保护-脱保护步骤来合成羟基化的斯蒂芬酯。
• Microwave Induced One Pot Process For The Preparation Of Arylethenes
  申请人：Sinha Kumar Arun

  公开号：US20080045752A1

  公开（公告）日：2008-02-21

  The invention entitled “A Microwave Induced One Pot Process for The Preparation of Arylethenes” provides a method for the preparation of commercially important 2- or 4-hydroxy substituted arylethenes like styrenes or stilbenes in one pot utilizing cheaper substrates in the form of 2- or 4-hydroxy substituted cinnamic acids and their derivatives as well as reagents in the form of base such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium bicarbonate, potassium carbonate, ammonium acetate, imidazole, methylimidazole and the combination thereof, with or without solvent such as dimethylformamide, dimethylsulfoxide, ethylene glycol, diethylene glycol, acetonitrile, acetone, methyl imidazoles, ionic liquid, water and the like. The reaction time vary from 1 min-12 hrs and yield of the products from 49-76% depending upon the base, acid, substrate source of heating monomode or multimode microwave or conventional. It is important to mention that the presence of 2- or 4-hydroxy substitution at phenyl ring of cinnamic acids and their derivatives is essential requirements towards formation of corresponding arylethenes in one step.

  这项名为“一锅法微波诱导制备芳基乙烯”的发明提供了一种在一个反应器中利用更便宜的底物（2-或4-羟基取代肉桂酸及其衍生物）和碱性试剂（如氢氧化钠，氢氧化钾，氢氧化锂，碳酸氢钠，碳酸钠，碳酸氢钾，碳酸钾，乙酸铵，咪唑，甲基咪唑和它们的组合物）制备商业上重要的2-或4-羟基取代的芳基乙烯（如苯乙烯或苯并乙烯）的方法。反应时间为1分钟至12小时，产率为49-76％，取决于碱性试剂、酸性试剂、底物、加热方式（单模或多模微波或传统方式）等因素。值得一提的是，肉桂酸及其衍生物苯环上的2-或4-羟基取代是制备相应芳基乙烯的必要条件，可以在一个步骤中完成。反应可以在溶剂（如二甲基甲酰胺、二甲基亚砜、乙二醇、二乙二醇、乙腈、丙酮、甲基咪唑、离子液体、水等）存在或不存在的情况下进行。
• Single step microwave induced process for the preparation of substituted stilbenes and its analogs
  申请人：Sinha Kumar Arun

  公开号：US20070276172A1

  公开（公告）日：2007-11-29

  The present invention relates to a single step, microwave induced process for the preparation of substituted stilbenes and its analogs. Particularly, provides a method for the preparation of commercially important 2- or 4-hydroxy substituted stilbenes in one pot utilizing cheaper substrates in the form of 2- or 4-hydroxy substituted arylaldehyde and/or phenylacetic acids as well as regents in the form of base such as collidine, triethylamine, pyridine, piperidine, sodium acetate, ammonium acetate, imidazole, methyl imidazoles and the like and/or acid such as formic acid, acetic acid, propionic acid and the like for a reaction time varying from 1 min-16 hrs depending upon microwave or conventional heating, without using decarboxylating agents with yield varying from 37-66% depending upon the base and/or acid, solvent and substrate used. It is important to mention that the presence of hydroxy substitution at 2- or 4-position of arylaldehyde and/or aryl acetic acid is essential requirements towards formation of stilbenes in one step.

  本发明涉及一种单步微波诱导过程，用于制备取代苯乙烯及其类似物。特别地，提供了一种在一个反应器中利用更便宜的底物，如2-或4-羟基取代芳基醛和/或苯乙酸，以及碱性试剂，如哌啶，三乙胺，吡啶，哌啶，乙酸钠，醋酸铵，咪唑，甲基咪唑等和/或酸性试剂，如甲酸，醋酸，丙酸等，反应时间从1分钟到16小时不等，取决于微波或常规加热，而不使用脱羧试剂，产率从37％到66％不等，取决于所使用的碱性和/或酸性试剂，溶剂和底物。需要指出的是，在芳基醛和/或芳基乙酸的2-或4-位存在羟基取代是形成单步合成苯乙烯的必要条件。