(Z)-3,5-di(tert-butyldimethylsilyloxy)-4'-methoxystilbene | 192710-88-6

• 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)-3,5-di(tert-butyldimethylsilyloxy)-4'-methoxystilbene
• 英文别名: tert-butyl-[3-[tert-butyl(dimethyl)silyl]oxy-5-[(Z)-2-(4-methoxyphenyl)ethenyl]phenoxy]-dimethylsilane
• CAS: 192710-88-6
• 化学式: C₂₇H₄₂O₃Si₂
• 分子量: 470.8
• InChiKey: DXZVZAJBYRSLRX-SEYXRHQNSA-N

物化性质

• 沸点：
  492.3±45.0 °C(predicted)
• 密度：
  0.978±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.63
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  (Z)-3,5-di(tert-butyldimethylsilyloxy)-4'-methoxystilbene 在 碘 作用下， 以 正庚烷 为溶剂， 反应 16.0h， 生成 (E)-3,5-di(tert-butyldimethylsilyloxy)-4'-methoxystilbene
  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
• 作为产物：
  描述：

  3,5-二羟基苯甲醛 在 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (Z)-3,5-di(tert-butyldimethylsilyloxy)-4'-methoxystilbene
  参考文献：
  名称：

  Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)

  摘要：

  (E)−3−(葡萄糖-β−D−果糖氧基)−4',5-二羟基联苯（resveratrol 3−β−D− glucoside， 梦他tributes A−1）， (2)− 2',3'-二羟基−3,4,4',5-四甲氧基−联苯（combretastatin A−1）， (Z)−3'-羟基−3,4,4',5-四甲氧基−联苯 (combretastatin A−4)， (Z)−2'-羟基−3,4,4',5-四甲氧基−联苯 (combretastatin iso−A−4)， α,β−双氢−2',3'-二羟基−3,4,4',5-四甲氧基−联苯（combretastatin B−1）及其相应的葡萄糖化物和相关物质通过 Wittig 反应和转移膜催化合成了。目前所合成的大部分化合物已经进行了生物活性测试（细胞抑制，细胞毒性，拟使之 arrest，神经毒性和抗血小板聚集作用）。 (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00087-6

文献信息

• Unexpected O-alkylation and ester migration in phenolic 2,3-diaryl-2,3-dihydrobenzo[b]furans
  作者：Henry Tran、Benjamin D. Dickson、David Barker

  DOI：10.1016/j.tetlet.2013.02.024

  日期：2013.4

  O-alkylation of 2-(4-methoxyphenyl)-5-hydroxy-3-[1,3-phenylene-bis(4-nitrobenzoate)]-2,3-dihydrobenzo[b]furan results in the unexpected hydrolysis of the nitrobenzoate esters, transfer of a 4-nitrobenzoic acid group to the 5-hydroxyl group and double alkylation of the newly formed 3,5-diphenol moiety. A range of alkyl halides can be used and give access to O-alkyl analogues of ε-viniferin.

  2-（4-甲氧基苯基）-5-羟基-3- [1,3-亚苯基-双（4-硝基苯甲酸酯）]-2,3-二氢苯并[ b ]呋喃的O-烷基化导致硝基苯甲酸酯的意外水解酯，将4-硝基苯甲酸基团转移到5-羟基基团上，以及新形成的3,5-二酚部分的双烷基化。可以使用一系列卤代烷，并且可以得到ε-葡萄素的O-烷基类似物。
• Antineoplastic Agents. 465. Structural Modification of Resveratrol:  Sodium Resverastatin Phosphate
  作者：George R. Pettit、Matthew P. Grealish、M. Katherine Jung、Ernest Hamel、Robin K. Pettit、J.-Charles Chapuis、Jean M. Schmidt

  DOI：10.1021/jm010119y

  日期：2002.6.1

  As an extension of structure/activity investigations of resveratrol (1), phenstatin (2c), and the cancer antiangiogenesis drug sodium combretastatin A-4 phosphate (2b), syntheses of certain related stilbenes (14) and benzophenones (16) were undertaken. The trimethyl ether derivative of (Z)-resveratrol (4a) exhibited the strongest activity (GI(50) = 0.01-0.001 mug/mL) against a minipanel of human cancer cell lines. A monodemethylated derivative (14c) was converted to prodrug 14n (sodium resverastatin phosphate) for further biological evaluation. The antitubulin and antimicrobial activities of selected compounds were also evaluated.
• WO2008/70872
  申请人：——

  公开号：——

  公开（公告）日：——