(E,E)-1-styryl-4-(4-hydroxystyryl)benzene | 251547-62-3

• 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,E)-1-styryl-4-(4-hydroxystyryl)benzene
• 英文别名: 4-[(E)-2-{4-[(E)-2-phenylethenyl]phenyl}ethenyl]phenol；4-[(E)-2-[4-[(E)-2-phenylethenyl]phenyl]ethenyl]phenol
• CAS: 251547-62-3
• 化学式: C₂₂H₁₈O
• 分子量: 298.384
• InChiKey: BDDHTYZSYBKJSA-GYIPPJPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (4-碘苄基)膦酸二乙酯 在 盐酸 、 苯基脲 、 sodium methylate 、 palladium diacetate 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成 (E,E)-1-styryl-4-(4-hydroxystyryl)benzene
  参考文献：
  名称：

  Phenolic Bis-styrylbenzenes as β-Amyloid Binding Ligands and Free Radical Scavengers

  摘要：

  Starting from bisphenolic bis-styrylbenzene DF-9 (4), P-amyloid (A beta) binding affinity and specificity for phenolic bis-styrylbenzenes, monostyrylbenzenes, and alkyne controls were determined by fluorescence titration with beta-amyloid peptide A beta(1-40) and a fluorescence assay using APP/PSI transgenic mouse brain sections. Bis-styrylbenzene SA R is derived largely from work on symmetrical compounds. This study is the first to describe A beta binding data for bis-styrylbenzenes unsymmetrical in the outer rings. With one exception, binding affinity and specificity were decreased by adding and/or changing the substitution pattern of phenol functional groups, changing the orientation about the central phenyl ring, replacing the alkene with alkyne bonds, or eliminating the central phenyl ring. The only compound with an A beta binding affinity and specificity comparable to 4 was its 3-hydroxy regioisomer 8. Like 4, 8 crossed the blood brain barrier and bound to A beta plaques in vivo. By use of a DPPH assay, phenol functional groups with papa orientations seem to be a necessary. but insufficient, criterion for good free radical scavenging properties in these compounds.

  DOI：

  10.1021/jm1006929

文献信息

• Pd-Catalyzed Orthogonal Knoevenagel/Perkin Condensation-Decarboxylation-Heck/Suzuki Sequences: Tandem Transformations of Benzaldehydes into Hydroxy-Functionalized Antidiabetic Stilbene-Cinnamoyl Hybrids and Asymmetric Distyrylbenzenes
  作者：Naina Sharma、Abhishek Sharma、Amit Shard、Rakesh Kumar、Saima、Arun K. Sinha

  DOI：10.1002/chem.201101174

  日期：2011.9.5

  Tandem reactions that involve chemoselective Knoevenagel/Perkin condensation–decarboxylation–Heck/Suzuki coupling or Heck–aldol sequences have been achieved. This enabled the first concise and efficient synthesis of several important hydroxy‐functionalized compound classes, such as stilbene–cinnamoyl hybrids (potent protein tyrosine phosphatase1B inhibitors), cinnamoyl–cinnamic acid hybrids, asymmetric

  已经实现了涉及化学选择性Knoevenagel / Perkin缩合-脱羧-Heck / Suzuki偶联或Heck-醛醇缩合序列的串联反应。这样就可以首次简洁有效地合成几种重要的羟基官能化化合物，例如二苯乙烯-肉桂酰基杂化物（强力蛋白酪氨酸磷酸酶1B抑制剂），肉桂酰基-肉桂酸杂化物，不对称二苯乙烯基苯和联芳基苯乙烯。先前报道的合成需要多个步骤和保护/脱保护操作。
• [EN] OPHTHALMIC FORMULATIONS OF AMYLOID- CONTRAST AGENTS AND METHODS OF USE THEREOF<br/>[FR] FORMULATIONS OPHTALMIQUES D'AGENTS DE CONTRASTE AMYLOÏDE ET PROCÉDÉS D'UTILISATION DE CELLES-CI
  申请人：NEUROPTIX CORP

  公开号：WO2008144065A1

  公开（公告）日：2008-11-27

  [EN] The invention provides ophthalmic formulations of Amyloid-ß contrast agents. Also provided are methods of using such formulations in the diagnosis of Alzheimer's Disease or a predisposition thereto as well as methods for the prognosis of Alzheimer's Disease.
  [FR] L'invention concerne des formulations ophtalmiques d'agents de contraste amyloïde-b. Des procédés d'utilisation de telles formulations dans le diagnostic de la maladie d'Alzheimer ou de la prédisposition à celle-ci ainsi que des procédés pour le pronostic de la maladie d'Alzheimer sont également décrits.