(Z)-4,3′-dimethoxystilbene

• 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: (Z)-4,3′-dimethoxystilbene
• 英文别名: 4Z-3,4'-dimethoxystilbene；1-methoxy-3-[(Z)-2-(4-methoxyphenyl)ethenyl]benzene
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: PMVLDTCOUSZSHN-SREVYHEPSA-N

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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  反-4,4'-二甲氧基芪	1,2-bis(4-methoxyphenyl)ethene	4705-34-4	C16H16O2	240.302
  4-甲氧基苯乙烯	4-Methoxystyrene	637-69-4	C9H10O	134.178
  间甲基苯甲醚	1-methoxy-3-methyl-benzene	100-84-5	C8H10O	122.167

反应信息

• 作为产物：
  描述：

  4-甲氧基苄醇 在 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 34.0h， 生成 (Z)-4,3′-dimethoxystilbene
  参考文献：
  名称：

  Quinone reductase induction activity of methoxylated analogues of resveratrol

  摘要：

  Agents that induce the activity of phase II enzymes play an important role in intervening with the carcinogenic process at the initiation stage. Resveratrol is well known for its chemopreventive activity against major stages of carcinogenesis. In this study, several methoxylated analogues of resveratrol were synthesized and evaluated for their ability to induce the activity of the phase H enzyme quinone reductase (QR). Methoxy groups serve to increase lipophilicity and improve metabolic stability. Compared to resveratrol, analogues with ortho-metboxy substituents were found to be more potent inducers of QR and to exert their activity in a qualitatively different manner. The greater induction activities associated with these stilbenoids serve as a useful starting point for the design of improved chemopreventive agents. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.12.012

文献信息

• Stereoselective Peterson Olefinations from Bench-Stable Reagents and<i>N</i>-Phenyl Imines
  作者：Manas Das、Atul Manvar、Maïwenn Jacolot、Marco Blangetti、Roderick C. Jones、Donal F. O'Shea

  DOI：10.1002/chem.201500475

  日期：2015.6.8

  The synthesis of bench‐stable α,α‐bis(trimethylsilyl)toluenes and tris(trimethylsilyl)methane is described and their use in stereoselective Peterson olefinations has been achieved with a wide substrate scope. Product stereoselectivity was poor with carbonyl electrophiles (E/Z ∼1:1 to 4:1) though this was significantly improved by employing the corresponding substituted N‐benzylideneaniline (up to 99:1)

  描述了台稳的α，α-双（三甲基甲硅烷基）甲苯和三（三甲基甲硅烷基）甲烷的合成，并已在较宽的底物范围内实现了它们在立体选择性Peterson烯烃中的应用。羰基亲电试剂的产物立体选择性差（E / Z约为1：1至4：1），尽管通过使用相应的取代N-苄叉基苯胺（最高达99：1）作为替代亲电试剂可以显着改善。烯化副产物被鉴定为N，N-双（三甲基甲硅烷基）苯胺，很容易通过酸水萃取从产物中分离出来。已经获得了自催化循环的证据。
• Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols
  作者：Malik Chalal、Dominique Vervandier-Fasseur、Philippe Meunier、Hélène Cattey、Jean-Cyrille Hierso

  DOI：10.1016/j.tet.2012.03.025

  日期：2012.5

  protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was

  Wittig反应和钯催化的Heck偶联的改进方案使人们可以方便地获得一系列前所未有的多官能化人工白藜芦醇衍生物。在改进的Wittig协议中，三甲基甲硅烷基被用作起始芳香族材料的酚功能的高度有价值的保护基。干净的O还进行了用碳酸亚乙酯对羟基化的对苯二甲酸酯进行的烷基化。因此，Wittig反应接着羟乙基化仅在二氧化碳作为废料的情况下一锅进行。另外，通过使用二茂铁基膦配体开发了钯催化的Heck偶联策略，并且不需要任何保护/脱保护序列就获得了多官能化的羟基苯乙烯基苯甲酸酯。这些程序最多引入六个官能团，这限制了反应步骤的数量，废物的毒性以及昂贵试剂的使用。
• Z-stilbenes derivatives and the pharmaceutical composition thereof
  申请人：Liou Jing-Ping

  公开号：US20080096973A1

  公开（公告）日：2008-04-24

  A series of Z-stilbenes derivatives are disclosed, which have the structure as shown by formula 1. In the structure of formula 1, X is hydrogen, NHR, or nitro group, and R is hydrogen. Y and Z is independently hydrogen, halogen, C 1 -C 10 alkyl, or C 1 -C 10 alkoxyl. Furthermore, A is hydrogen, hydroxyl, or amino group. The compounds of the present invention have both aqueous solubility and anti-tumor activity. The Z-stilbenes derivatives of the present invention can further include a pharmaceutical carrier to form pharmaceutical compositions as potent anti-mitotic agents and anti-cancer agents.

  揭示了一系列Z-亚苄烯衍生物，其具有由化学式1所示的结构。在化学式1的结构中，X为氢、NHR或硝基基团，而R为氢。Y和Z分别为氢、卤素、C1-C10烷基或C1-C10烷氧基。此外，A为氢、羟基或氨基。本发明的化合物具有水溶性和抗肿瘤活性。本发明的Z-亚苄烯衍生物可以进一步包括药用载体，形成制剂作为强效抗有丝分裂剂和抗癌剂。
• Active Ruthenium (0) Nanoparticles Catalyzed Wittig-Type Olefination Reaction
  作者：Vivek Srivastava

  DOI：10.1007/s10562-016-1943-y

  日期：2017.3

  with low-average selectivity. The proposed methodology is especially efficient for the synthesis of stilbenes as they were synthesized in the absence of any additive (as a hydrogen acceptor). The new catalytic system was also successfully applied for the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol and DMU-212.Graphical Abstract

  五种不同的 Ru 金属前驱体在 50 °C 的氢气氛（4 bar）下在咪唑鎓基离子液体中还原，以获得分散良好且稳定的 Ru 纳米粒子。透射电子显微镜 (TEM) 分析证实了直径为 5 nm (±0.5) 的分散良好的离子液体介导的 Ru 粒子 (Ru NPs) 的大小。这些钌纳米颗粒（在离子液体中）用于在温和的反应环境（70°C 和 1 小时）下进行 Wittig 型烯化反应。以较低的平均选择性以良好的收率获得了相应的芪。所提出的方法对于二苯乙烯的合成特别有效，因为它们是在没有任何添加剂（作为氢受体）的情况下合成的。新的催化体系也成功应用于合成多甲氧基和多羟基二苯乙烯，
• Photooxygenation of stilbenes in zeolite by excitation of their contact charge transfer complexes with oxygen
  作者：Haruhiko Takeya、Yasunao Kuriyama、Masanobu Kojima

  DOI：10.1016/s0040-4039(98)01224-6

  日期：1998.8

  Contact charge transfer (CCT) complexes of trans-stilbenes with oxygen molecules were formed in zeolite NaY. Excitation of the CCT bands by a 313-nm wavelength light produced the corresponding benzaldehydes through an electron transfer reaction to generate stilbene cation radicals and superoxide anion radical. Irradiation of the CCT complexes by a 254-nm wavelength light, by contrast, gave rise to

  在沸石NaY中形成了反式对苯二酚与氧分子的接触电荷转移（CCT）络合物。313 nm波长的光激发CCT带，通过电子转移反应产生相应的苯甲醛，生成二苯乙烯阳离子自由基和超氧阴离子自由基。相比之下，用254 nm波长的光照射CCT络合物会引起异构化和菲的形成，而不会产生任何氧化产物，就像在溶液中氧气下的光反应一样。