dehydrobrittonin A | 61240-21-9

• 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: dehydrobrittonin A
• 英文别名: 1,2,3-trimethoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene
• CAS: 61240-21-9
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: DUESHOUIPOUGCU-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 四(三苯基膦)钯 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 22.58h， 生成 dehydrobrittonin A
  参考文献：
  名称：

  A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors

  摘要：

  A series of combretastatin derivatives were designed and synthesised by a two-step stereoselective synthesis by use of Wittig olefination followed by Suzuki cross-coupling. Interestingly, all new compounds (2a-2i) showed potent cell-based antiproliferative activities in nanomolar concentrations. Among the compounds, 2a, 2b and 2e were the most active across three cancer cell lines. In addition, these compounds inhibited the polymerisation of tubulin in vitro more efficiently than CA-4. They caused cell cycle arrest in G(2)/M phase further confirming their ability to inhibit tubulin polymerisation.

  DOI：

  10.1016/j.bmc.2020.115684

文献信息

• Ruthenium nanoparticle-intercalated montmorillonite clay for solvent-free alkene hydrogenation reaction
  作者：Praveenkumar Upadhyay、Vivek Srivastava

  DOI：10.1039/c4ra12324g

  日期：——

  Well-characterized, ruthenium nanoparticle-intercalated montmorillonite clay was used as a catalyst in solvent-free alkene hydrogenation reactions and the corresponding products were obtained in good yields. The catalytic activity of ruthenium nanoparticle-intercalated montmorillonite clay was successfully tested with 16 different functionalized and non-functionalized alkenes. Apart from alkene reduction

  表征良好的钌纳米颗粒插层蒙脱土用作无溶剂烯烃加氢反应的催化剂，并以良好的收率获得了相应的产物。用16种不同的官能化和非官能化烯烃成功地测试了钌纳米粒子插层蒙脱土的催化活性。除烯烃还原外，还在Wittig型反应中测试了钌纳米粒子插层的蒙脱土粘土以获得脱氢布雷顿通素A的作用，脱氢溴通心粉素A是合成布雷顿酮A的重要中间体。发现钌纳米粒子插层的蒙脱石粘土对合成氢溴酸蒙脱石具有活性。脱氢布雷顿酮A和布雷顿通酯A。催化剂循环使用9次的能力以及较低的催化剂负载量，
• Wittig-Type Olefination of Alcohols Promoted by Nickel Nanoparticles: Synthesis of Polymethoxylated and Polyhydroxylated Stilbenes
  作者：Francisco Alonso、Paola Riente、Miguel Yus

  DOI：10.1002/ejoc.200900951

  日期：2009.12

  Spanish Ministerio de Educacion y Ciencia (MEC); Grant Number: CTQ2007-65218, CSD2007-00006.

  西班牙教育与科学部长（MEC）；授权号：CTQ2007-65218，CSD2007-00006。
• Synthesis of resveratrol, DMU-212 and analogues through a novel Wittig-type olefination promoted by nickel nanoparticles
  作者：Francisco Alonso、Paola Riente、Miguel Yus

  DOI：10.1016/j.tetlet.2009.04.023

  日期：2009.6

  A novel synthesis of resveratrol, DMU-212 and analogues is presented using benzyl alcohols as phosphorus ylide partners in a one-pot Wittig-type olefination reaction promoted by nickel nanoparticles.

  提出了一种新的白藜芦醇，DMU-212和类似物的合成方法，该方法使用苄醇作为磷的叶酸伙伴，在镍纳米粒子促进的一锅Wittig型烯烃化反应中。
• Synthesis of 2,2'-diacyl-1,1'-biaryls. Regiocontrolled protection of ketones in unsymmetrically substituted 9,10-phenanthrenequinones
  作者：Miljenko Mervic、Eugene Ghera

  DOI：10.1021/jo01311a034

  日期：1980.11
• A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors
  作者：Natalie G. Barnes、Anthony W. Parker、Amjed A. Ahmed Mal Ullah、Patricia A. Ragazzon、John A. Hadfield

  DOI：10.1016/j.bmc.2020.115684

  日期：2020.10

  A series of combretastatin derivatives were designed and synthesised by a two-step stereoselective synthesis by use of Wittig olefination followed by Suzuki cross-coupling. Interestingly, all new compounds (2a-2i) showed potent cell-based antiproliferative activities in nanomolar concentrations. Among the compounds, 2a, 2b and 2e were the most active across three cancer cell lines. In addition, these compounds inhibited the polymerisation of tubulin in vitro more efficiently than CA-4. They caused cell cycle arrest in G(2)/M phase further confirming their ability to inhibit tubulin polymerisation.