(E)-3,5-di(tert-butyldimethylsilyloxy)-4'-methoxystilbene | 192710-87-5

• 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)-3,5-di(tert-butyldimethylsilyloxy)-4'-methoxystilbene
• 英文别名: tert-butyl-[3-[tert-butyl(dimethyl)silyl]oxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]phenoxy]-dimethylsilane
• CAS: 192710-87-5
• 化学式: C₂₇H₄₂O₃Si₂
• 分子量: 470.8
• InChiKey: DXZVZAJBYRSLRX-OUKQBFOZSA-N

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：

  (E)-3,5-di(tert-butyldimethylsilyloxy)-4'-methoxystilbene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到白藜芦醇-4'-甲醚
  参考文献：
  名称：

  酚2,3,3-二芳基-2,3-二氢苯并[ b ]呋喃中的意外O-烷基化和酯迁移

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2013.02.024
• 作为产物：
  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

文献信息

• 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：——