2-(2’,2’-dibromovinyl)-1,3,5-trimethoxybenzene | 1330633-87-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2’,2’-dibromovinyl)-1,3,5-trimethoxybenzene
• 英文别名: 2-(2',2'-dibromovinyl)-1,3,5-trimethoxybenzene；2-(2,2-dibromovinyl)-1,3,5-trimethoxybenzene；2',2'-dibromovinyl-1,3,5-trimethoxybenzene；2-(2,2-Dibromoethenyl)-1,3,5-trimethoxybenzene
• CAS: 1330633-87-8
• 化学式: C₁₁H₁₂Br₂O₃
• 分子量: 352.022
• InChiKey: QVAPMJWHAKEJSE-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  405.4±40.0 °C(Predicted)
• 密度：
  1.659±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-(2’,2’-dibromovinyl)-1,3,5-trimethoxybenzene 在 正丁基锂 、 sodium dithionite 、 三乙基硼 作用下， 以 四氢呋喃 、 正己烷 、 水 、 丙酮 、 苯 为溶剂， 反应 3.25h， 生成 (E)-2',4',6'-trimethoxystyryl-4-methoxy-3-aminobenzyl sulfide
  参考文献：
  名称：

  Discovery of a Clinical Stage Multi-Kinase Inhibitor Sodium (E)-2-{2-Methoxy-5-[(2′,4′,6′-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na): Synthesis, Structure–Activity Relationship, and Biological Activity

  摘要：

  Cyclin D proteins are elevated in many cancer cells, and targeted deletion of cyclin D1 gene in the mammary tissues protects mice from breast cancer, Accordingly, there is an increasing awareness of this novel nonenzymatic target for cancer therapeutics. We have developed novel, nonalkylating styrylbenzylsulfones that induce cell death in wide variety of cancer cells without affecting the proliferation and survival of normal cells. The development of derivatized styrylbenzylsulfones followed logically from a tumor cell cytotoxicity screen performed in our laboratory that did not have an a priori target profile. Modifications of some of the precursor molecules led to lead optimization with regard to tumor cell cytotoxicity. In this report we describe the synthesis and structure-activity relationships of novel, nonalkylating (E)-styrylbenzylsulfones and the development of the novel anticancer agent sodium (E)-2-{2-methoxy-5-[(2',4',6'-trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na), which is in phase III trials for myelodysplastic syndromes (MDS) associated with aberrant expression of cyclin D proteins.

  DOI：

  10.1021/jm200570p
• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 以72的产率得到2-(2’,2’-dibromovinyl)-1,3,5-trimethoxybenzene
  参考文献：
  名称：

  J. Med. Chem. 2011, 54, 6254-6276

  摘要：

  DOI：

文献信息

• Hydrothiolation of benzyl mercaptan to arylacetylene: application to the synthesis of (E) and (Z)-isomers of ON 01910·Na (Rigosertib®), a phase III clinical stage anti-cancer agent
  作者：Venkat R. Pallela、Muralidhar R. Mallireddigari、Stephen C. Cosenza、Balaiah Akula、D. R. C. Venkata Subbaiah、E. Premkumar Reddy、M. V. Ramana Reddy

  DOI：10.1039/c3ob27220f

  日期：——

  A stereoselective and efficient method for free radical addition of benzyl thiol to aryl acetylene in the presence of Et3B-hexane has been developed for the synthesis of (Z) and (E)-styryl benzyl sulfides where base catalyzed hydrothiolations have failed. The scope of this reaction was successfully extended for the synthesis of (E)-ON 01910·Na, a phase III clinical stage anti-cancer agent and its inactive

  一种立体选择性且高效的自由基加成方法苄硫醇在 Et 3 B-己烷存在下将芳基乙炔转化为芳基乙炔已被开发用于合成 ( Z ) 和 ( E )-苯乙烯基苄基硫醚，其中碱催化的氢硫醇化已失败。该反应范围被成功扩展，用于合成III期临床抗癌药物( E )-ON 01910·Na及其无活性几何异构体( Z )-ON 01910·Na。有趣的是，与Z异构体相比，所有合成的E异构体都对癌细胞表现出更好的细胞毒性。
• Comparative Analysis of Conjugated Alkynyl Chromophore-Triazacyclononane Ligands for Sensitized Emission of Europium and Terbium
  作者：Marine Soulié、Frédéric Latzko、Emmanuel Bourrier、Virginie Placide、Stephen J. Butler、Robert Pal、James W. Walton、Patrice L. Baldeck、Boris Le Guennic、Chantal Andraud、Jurriaan M. Zwier、Laurent Lamarque、David Parker、Olivier Maury

  DOI：10.1002/chem.201402415

  日期：2014.7.7

  A series of europium and terbium complexes based on a functionalized triazacyclononane carboxylate or phosphinate macrocyclic ligand is described. The influence of the anionic group, that is, carboxylate, methylphosphinate, or phenylphosphinate, on the photophysical properties was studied and rationalized on the basis of DFT calculated structures. The nature, number, and position of electron‐donating

  描述了基于官能化的三氮杂环壬烷羧酸盐或次膦酸酯大环配体的一系列of和ter配合物。阴离子基团，即羧酸根，甲基次膦酸根或苯基次膦酸根，对光物理性质的影响进行了研究，并在DFT计算结构的基础上进行了合理化。在同一苯基乙炔基支架内，给电子或吸电子芳基取代基的性质，数量和位置发生系统性变化，以优化相应euro配合物的亮度并研究其双光子吸收特性。最后，在细胞成像应用中检查了complex络合物，并对选定的selected络合物作为潜在的氧传感器进行了研究。
• Very bright, enantiopure europium(<scp>iii</scp>) complexes allow time-gated chiral contrast imaging
  作者：Andrew T. Frawley、Robert Pal、David Parker

  DOI：10.1039/c6cc07313a

  日期：——

  Chiral image contrast is reported with very bright enantiopure europium complexes that emit circularly polarized light.

  手性图像对比是使用非常明亮的对映纯的铕配合物报告的，这些配合物发射圆偏振光。
• Org. Biomol. Chem. 2013, 11, 1964-1977
  作者：

  DOI：——

  日期：——