(Z)-3-(tert-butyldimethylsilyloxy)-4,4'-methoxystilbene | 945657-72-7

• 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-(tert-butyldimethylsilyloxy)-4,4'-methoxystilbene
• 英文别名: tert-butyl-[2-methoxy-5-[(Z)-2-(4-methoxyphenyl)ethenyl]phenoxy]-dimethylsilane
• CAS: 945657-72-7
• 化学式: C₂₂H₃₀O₃Si
• 分子量: 370.564
• InChiKey: AXUUNJCUMROYPZ-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-(tert-butyldimethylsilyloxy)-4,4'-methoxystilbene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以94%的产率得到2-methoxy-5-[(Z)-2-(4-methoxyphenyl)ethenyl]phenol
  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：

  叔丁基二甲基氯硅烷 在 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.0h， 生成 (Z)-3-(tert-butyldimethylsilyloxy)-4,4'-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