(E)-2,6-dimethoxystilbene | 55288-33-0

• 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)-2,6-dimethoxystilbene
• 英文别名: 1,3-Dimethoxy-2-[(1E)-2-phenylethenyl]benzene；1,3-dimethoxy-2-[(E)-2-phenylethenyl]benzene
• CAS: 55288-33-0
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: CXYVPZCCKRXMJO-VAWYXSNFSA-N

物化性质

• 熔点：
  45-46 °C
• 沸点：
  369.4±11.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2,6-dimethoxystilbene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以99%的产率得到2,6-dimethoxybibenzyl
  参考文献：
  名称：

  Synthesis and Nematocidal Activity of Hydroxystilbenes

  摘要：

  通过一种新的(Z)-(E)异构化方法随后进行脱甲基反应，从(E)/(Z)混合甲氧基二苯乙烯中合成了多种(E)-羟基二苯乙烯。当甲氧基二苯乙烯脱甲基生成羟基二苯乙烯时，表现出杀线虫活性。为了产生这种活性，C-2或C-3位置上必须有一个羟基。因此，2-羟基-、3-羟基-、2,6-二羟基-、3,4-二羟基-、3,5-二羟基-、2,2'-二羟基-、3,3'-二羟基-、3,4'-二羟基-、2-羟基-4-甲氧基-、5-羟基-2-甲氧基-、2-羟基-6-甲氧基-、6-烯丙氧基-2-羟基-、3-羟基-5-甲氧基-和5-烯丙氧基-3-羟基二苯乙烯表现出相当强的杀线虫活性。5-烯丙氧基-3-羟基二苯乙烯的活性最强[最小致死浓度（MLC）=30 μM]。(E)和(Z)异构体的活性相当。二氢衍生物，羟基联苄中也保留了这些活性，尽管较弱。

  DOI：

  10.1248/cpb.40.1130
• 作为产物：
  描述：

  苯乙烯 、 2,6-二甲氧基苯甲酸 在 palladium(II) trifluoroacetate 、 对苯醌 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以94%的产率得到(E)-2,6-dimethoxystilbene
  参考文献：
  名称：

  室温下脱羧Heck反应的底物依赖性机理

  摘要：

  我们在这里报道了在室温下芳烃羧酸和烯烃之间的Pd（II）催化的Heck型偶联。从机理上讲，反应以两种不同的途径进行，富电子的底物经历钯（II）催化的脱羧反应，缺电子的底物通过银（I）辅助的脱羧反应进行。二甲基亚砜（DMSO）或硫化物配体在反应结果中分别具有正作用和负作用。结合本方案用于在温和的反应条件下进行肽修饰。

  DOI：

  10.1021/acs.joc.6b00100

文献信息

• 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。
• Pd(O₂CCF₃)₂/Benzoquinone: A Versatile Catalyst System for the Decarboxylative Olefination of Arene Carboxylic Acids
  作者：Peng Hu、Jian Kan、Weiping Su、Maochun Hong

  DOI：10.1021/ol9007553

  日期：2009.6.4

  A versatile palladium catalyst system was developed to effect the decarboxylative Heck coupling of a variety of arenecarboxylic acids with a wide range of olefins. The key to obtaining the efficient catalyst system is the use of 1-adamatanecarboxylic acid as additive. Alkyl-substituted olefins with coordinating groups were observed to provide significantly improved regioselectivity compared with other alkyl-substituted olefins lacking coordinating groups, and the acetate group of allylic ester was also tolerated in this reaction.
• Development of a Decarboxylative Palladation Reaction and Its Use in a Heck-type Olefination of Arene Carboxylates
  作者：Andrew G. Myers、Daisuke Tanaka、Michael R. Mannion

  DOI：10.1021/ja027523m

  日期：2002.9.1

  The development of a palladium-catalyzed decarboxylative coupling reaction of arene carboxylates with olefinic substrates is described. The optimized procedure for decarboxylative palladation employs Pd(O2CCF3)2 as catalyst (0.2 equiv) in the presence of Ag2CO3 (3 equiv) in the solvent 5% DMSO-DMF and proceeds at temperatures of 80-120 degrees C with a wide range of arene carboxylates and alkenes as substrates. The process is proposed to proceed by an initial Ar-SE reaction involving ipso attack of an electrophilic Pd(II) intermediate on an arene carboxylate to form an arylpalladium(II) species with loss of carbon dioxide. This intermediate is then proposed to react with an olefinic substrate by steps common to the Heck coupling process. Reoxidation of the liberated Pd(0) in situ is proposed to establish the catalytic cycle.
• Substituted <i>trans</i>-Stilbenes, Including Analogues of the Natural Product Resveratrol, Inhibit the Human Tumor Necrosis Factor Alpha-Induced Activation of Transcription Factor Nuclear Factor KappaB
  作者：Justin J. Heynekamp、Waylon M. Weber、Lucy A. Hunsaker、Amanda M. Gonzales、Robert A. Orlando、Lorraine M. Deck、David L. Vander Jagt

  DOI：10.1021/jm060630x

  日期：2006.11.30

  The transcription factor nuclear factor kappaB (NF-kappa B), which regulates expression of numerous antiinflammatory genes as well as genes that promote development of the prosurvival, antiapoptotic state is up-regulated in many cancer cells. The natural product resveratrol, a polyphenolic trans-stilbene, has numerous biological activities and is a known inhibitor of activation of NF-kappa B, which may account for some of its biological activities. Resveratrol exhibits activity against a wide variety of cancer cells and has demonstrated activity as a cancer chemopreventive against all stages, i.e., initiation, promotion, and progression. The biological activities of resveratrol are often ascribed to its antioxidant activity. Both antioxidant activity and biological activities of analogues of resveratrol depend upon the number and location of the hydroxy groups. In the present study, phenolic analogues of resveratrol and a series of substituted trans-stilbenes without hydroxy groups were compared with resveratrol for their abilities to inhibit the human tumor necrosis factor alpha-induced (TNF-alpha) activation of NF-kappa B, using the Panomics NF-kappa B stable reporter cell line 293/NF-kappa B-luc. A series of 75 compounds was screened to identify substituted trans-stilbenes that were more active than resveratrol. Dose-response studies of the most active compounds were carried out to obtain IC50 values. Numerous compounds were identified that were more active than resveratrol, including compounds that were devoid of hydroxy groups and were 100-fold more potent than resveratrol. The substituted trans-stilbenes that were potent inhibitors of the activation of NF-kappa B generally did not exhibit antioxidant activity. The results from screening were confirmed using BV-2 microglial cells where resveratrol and analogues were shown to inhibit LPS-induced COX-2 expression.
• [EN] THERAPEUTIC AGENTS FOR SKIN DISEASES AND CONDITIONS<br/>[FR] AGENTS THÉRAPEUTIQUES POUR MALADIES ET AFFECTIONS CUTANÉES
  申请人：STC UNM

  公开号：WO2015085143A3

  公开（公告）日：2015-07-30