3,6,8-三溴-7-羟基香豆素 | 1009809-44-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 3,6,8-三溴-7-羟基香豆素
• 英文名称: 3,6,8-tribromo-7-hydroxycoumarin
• 英文别名: 3,6,8-Tribromo-7-hydroxychromen-2-one
• CAS: 1009809-44-2
• 化学式: C₉H₃Br₃O₃
• 分子量: 398.833
• InChiKey: NILSSGIDSAQCBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-羟基香豆素 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以26%的产率得到3,6,8-三溴-7-羟基香豆素
  参考文献：
  名称：

  An efficient regioselective bromination protocol of activated coumarins using 2,4,4,6-tetrabromo-2,5-cyclohexadienone

  摘要：

  在乙腈中，2,4,4,6-四溴-2,5-环己二酮介导的对活化香豆素的溴化反应以高区域选择性和良好至优良的产率完成。发现溴化的选择性和效率在很大程度上取决于电子因素，特别是从电子给予的7-氧代取代基到α-吡喃酮部分的C-3位置的电子撤离程度，通过共轭共振和在反应介质中存在水和四正丁基溴化铵等亲核添加剂。反应的唯一副产物通过氧化与KBr−KBrO₃转化回试剂，试剂可以循环使用三次而不会显著损失效率。

  DOI：

  10.1139/cjc-2013-0230

文献信息

• Electrochemical bromination of electron-rich compounds employing LiBr as a “Br” source
  作者：Hui-juan Chen、Xiao-xue Jiang、Hong-ji Shi、Ming-ming Li、Kou Wang

  DOI：10.1016/j.tetlet.2024.154927

  日期：2024.3

  A direct electrochemical-mediated CH bromination strategy of electron-rich compound is established using LiBr as a “Br” source under transition metal-free and oxidant-free catalysis condition. This method is performed in a green and sustainable system. A wide range of electron-rich compounds were found to be compatible, providing the corresponding products with moderate yields.

  以LiBr为“Br”源，在无过渡金属和无氧化剂的催化条件下，建立了一种直接电化学介导的富电子化合物CH溴化策略。该方法是在绿色且可持续的系统中进行的。人们发现多种富电子化合物是相容的，从而提供了具有中等产率的相应产物。
• Coumarin as Attractive Casein Kinase 2 (CK2) Inhibitor Scaffold: An Integrate Approach To Elucidate the Putative Binding Motif and Explain Structure–Activity Relationships
  作者：Adriana Chilin、Roberto Battistutta、Andrea Bortolato、Giorgio Cozza、Samuele Zanatta、Giorgia Poletto、Marco Mazzorana、Giuseppe Zagotto、Eugenio Uriarte、Adriano Guiotto、Lorenzo A. Pinna、Flavio Meggio、Stefano Moro

  DOI：10.1021/jm070909t

  日期：2008.2.1

  Casein kinase 2 (CK2) is an ubiquitous, essential, and highly pleiotropic protein kinase whose abnormally high constitutive activity is suspected to underlie its pathogenic potential in neoplasia and other diseases. Recently, using different virtual screening approaches, we have identified several novel CK2 inhibitors. In particular, we have discovered that coumarin moiety can be considered an attractive CK2 inhibitor scaffold. In the present work, we have synthetized and tested a small library of coumarins (more than 60), rationalizing the observed structure-activity relationship. Moreover, the most promising inhibitor, 3,8-dibromo-7-hydroxy-4-methylchromen-2-one (DBC), has been also crystallized in complex with CK2, and the experimental binding mode has been used to derive a linear interaction energy (LIE) model.