(E)-1-(4-tert-butylstyryl)-3,5-dimethoxybenzene | 1258410-98-8

• 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)-1-(4-tert-butylstyryl)-3,5-dimethoxybenzene
• 英文别名: (E)-4'-tert-butyl-3,5-dimethoxystilbene；1-[(E)-2-(4-tert-butylphenyl)ethenyl]-3,5-dimethoxybenzene
• CAS: 1258410-98-8
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: IDFIYQJCIUPDIT-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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)-1-(4-tert-butylstyryl)-3,5-dimethoxybenzene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到5-[(E)-2-(4-tert-butylphenyl)ethenyl]benzene-1,3-diol
  参考文献：
  名称：

  Design, synthesis, and evaluation of resveratrol derivatives as Aß1–42 aggregation inhibitors, antioxidants, and neuroprotective agents

  摘要：

  A series of novel resveratrol derivatives were designed, synthesised and evaluated as potential therapeutic agents for the treatment of Alzheimer's disease. Among these compounds, compound 7l, (E)-5-(4-(isopropylamino)styryl)benzene-1,3-diol, exhibited potent beta-amyloid aggregation inhibition activity, which was confirmed by a ThT fluorescence assay (71.65% at 20 mu M) and transmission electron microscopy (TEM). Compound 7l also exhibited good antioxidant activity (4.12 Trolox equivalents in an oxygen radical absorbance capacity assay and a 37% reduction in reactive oxygen species in cells at 10 mu M). The cytotoxicity analysis of compounds 7f, 7i, 7j and 7l indicated that these compounds have lower toxicities than resveratrol at 60 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.105
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 吡啶 、 sodium methylate 、 三溴化磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 (E)-1-(4-tert-butylstyryl)-3,5-dimethoxybenzene
  参考文献：
  名称：

  Design, synthesis, and evaluation of resveratrol derivatives as Aß1–42 aggregation inhibitors, antioxidants, and neuroprotective agents

  摘要：

  A series of novel resveratrol derivatives were designed, synthesised and evaluated as potential therapeutic agents for the treatment of Alzheimer's disease. Among these compounds, compound 7l, (E)-5-(4-(isopropylamino)styryl)benzene-1,3-diol, exhibited potent beta-amyloid aggregation inhibition activity, which was confirmed by a ThT fluorescence assay (71.65% at 20 mu M) and transmission electron microscopy (TEM). Compound 7l also exhibited good antioxidant activity (4.12 Trolox equivalents in an oxygen radical absorbance capacity assay and a 37% reduction in reactive oxygen species in cells at 10 mu M). The cytotoxicity analysis of compounds 7f, 7i, 7j and 7l indicated that these compounds have lower toxicities than resveratrol at 60 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.105

文献信息

• Synthesis of Stilbene and Distyrylbenzene Derivatives through Rhodium-Catalyzed<i>Ortho</i>-Olefination and Decarboxylation of Benzoic Acids
  作者：Satoshi Mochida、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol1027392

  日期：2010.12.17

  Ortho-substituted benzoic acids efficiently undergo precisely ordered ortho-olefination/decarboxylation upon treatment with styrenes in the presence of a rhodium catalyst and silver salt oxidant to afford the corresponding meta-substituted stilbene derivatives. The selective syntheses of 1,3- and 1,4-distyrylbenzenes have also been realized through the reactions of simple benzoic acid and phthalic

  邻-取代的苯甲酸有效离岗精确有序邻-olefination /脱羧在与在铑催化剂和银盐氧化剂，得到相应的存在的苯乙烯治疗间-取代的二苯乙烯衍生物。1，3-和1，4-二苯乙烯基苯的选择性合成也已经通过在相似条件下分别通过简单的苯甲酸和邻苯二甲酸与苯乙烯的反应来实现。
• Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group
  作者：Satoshi Mochida、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo200509m

  日期：2011.5.6

  The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. alpha,beta-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the beta-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.