(E)-3,4,5-trimethoxy-2-styrylbenzaldehyde | 1333172-99-8

• 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)-3,4,5-trimethoxy-2-styrylbenzaldehyde
• CAS: 1333172-99-8
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: FLWOHLUXBOJGQL-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  硝基甲烷 、 (E)-3,4,5-trimethoxy-2-styrylbenzaldehyde 在 ammonium acetate 作用下， 以90%的产率得到(E)-1,2,3-trimethoxy-5-((E)-2-nitrovinyl)-4-styrylbenzene
  参考文献：
  名称：

  Design and Synthesis of Resveratrol-Based Nitrovinylstilbenes as Antimitotic Agents

  摘要：

  A new series of resveratrol analogues was designed, synthesized, and demonstrated to be tubulin polymerization inhibitors. Most of these compounds exhibited antiproliferative activity and inhibited in vitro tubulin polymerization effectively at concentrations of 4.4-68.1 and 17-62 mu M, respectively. Flow cytometry studies showed that compounds 7c, 7e, and 7g arrested cells in the G2/M phase of the cell cycle. Immunocytochemistry revealed loss of intact microtubule structure in cells treated with 7c and 7e. Docking of compounds 7c and 7e with tubulin suggested that the A-ring of the compounds occupies the colchicine binding site of tubulin, which coordinates with Cys241, Leu242, Ala250, Val318, Val328, and I378, and that the nitrovinyl side chain forms two hydrogen bonds with the main loop of the beta-chain at Asn249 and Ala250.

  DOI：

  10.1021/jm200639r
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 potassium phosphate 、 溴 、 palladium diacetate 、 溶剂黄146 作用下， 以 二氯甲烷 、 异丁酰胺 为溶剂， 反应 12.0h， 生成 (E)-3,4,5-trimethoxy-2-styrylbenzaldehyde
  参考文献：
  名称：

  Design and Synthesis of Resveratrol-Based Nitrovinylstilbenes as Antimitotic Agents

  摘要：

  A new series of resveratrol analogues was designed, synthesized, and demonstrated to be tubulin polymerization inhibitors. Most of these compounds exhibited antiproliferative activity and inhibited in vitro tubulin polymerization effectively at concentrations of 4.4-68.1 and 17-62 mu M, respectively. Flow cytometry studies showed that compounds 7c, 7e, and 7g arrested cells in the G2/M phase of the cell cycle. Immunocytochemistry revealed loss of intact microtubule structure in cells treated with 7c and 7e. Docking of compounds 7c and 7e with tubulin suggested that the A-ring of the compounds occupies the colchicine binding site of tubulin, which coordinates with Cys241, Leu242, Ala250, Val318, Val328, and I378, and that the nitrovinyl side chain forms two hydrogen bonds with the main loop of the beta-chain at Asn249 and Ala250.

  DOI：

  10.1021/jm200639r

文献信息

• Nanocrystalline Titania-Supported Palladium(0) Nanoparticles for Suzuki-Miyaura Cross-Coupling of Aryl and Heteroaryl Halides
  作者：B. Sreedhar、Divya Yada、P. Surendra Reddy

  DOI：10.1002/adsc.201100012

  日期：2011.10

  The Suzuki cross-coupling reaction of various aryl and heteroaryl halides with arylboronic and heteroarylboronic acids was studied using a titania-supported palladium(0) catalyst at room temperature under air. The conversion and selectivity results obtained for many substrates were excellent and similar to those provided by more active or even homogeneous catalysts. The methodology is similarly effective

  使用二氧化钛负载的钯（0）催化剂在室温下于空气中研究了各种芳基和杂芳基卤化物与芳基硼酸和杂芳基硼酸的Suzuki交叉偶联反应。对于许多底物，获得的转化率和选择性结果极好，与活性更高甚至均相的催化剂所提供的结果相似。使用2-溴-3,4,5-三甲氧基苯甲醛作为偶合伙伴，该方法同样有效，并获得了高收率的产品。此外，已表明其可用于合成三联苯和四联苯。通过简单的过滤从反应中定量回收催化剂，并重复使用多个循环，而活性没有明显损失。