ethyl 5-bromo-2-oxo-2H-chromene-3-carboxylate | 934358-12-0

• 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
• 英文名称: ethyl 5-bromo-2-oxo-2H-chromene-3-carboxylate
• 英文别名: 5-bromo-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester；5-bromo-3-carbethoxycoumarin；ethyl 5-bromo-2-oxochromene-3-carboxylate
• CAS: 934358-12-0
• 化学式: C₁₂H₉BrO₄
• 分子量: 297.105
• InChiKey: VFDDEAPBGGOEPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-bromo-2-oxo-2H-chromene-3-carboxylate 在 sodium hydroxide 作用下， 反应 2.0h， 以47%的产率得到5-bromo-3-coumarincarboxylic acid
  参考文献：
  名称：

  Coumarin as Attractive Casein Kinase 2 (CK2) Inhibitor Scaffold: An Integrate Approach To Elucidate the Putative Binding Motif and Explain Structure–Activity Relationships

  摘要：

  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.

  DOI：

  10.1021/jm070909t
• 作为产物：
  描述：

  间(三甲基硅氧基)溴苯 在 N,N-二异丙基乙胺 、 cesium fluoride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 ethyl 5-bromo-2-oxo-2H-chromene-3-carboxylate
  参考文献：
  名称：

  选择性生成3-卤代芳烃的Aryne前体：制备及其在合成反应中的应用

  摘要：

  研究了新的3-卤代芳烃前体2a-2h的合成和反应。的邻- （三甲基硅烷基）三氟甲磺酸的芳基的前体2A-2H是通过涉及一个简单的程序来制备ö -trimethylsilylation和三甲基甲硅烷基，随后三氟甲磺酸化的迁移。新的前体的显着特征是通过抑制竞争性的硫-弗里斯重排选择性地生成了3-卤代芳烃，这是使用众所周知的3-卤代芳烃前体的反应问题。通过在几个反应中的直接比较，证实了新的前体2a优于典型的前体1。前体2a–2h的应用 还报道了杂环的合成。

  DOI：

  10.1021/acs.joc.0c01669

文献信息

• Solvent-Free FeCl3-Assisted Electrophilic Fluorine-Catalyzed Knoevenagel Condensation to Yield α,β-Unsaturated Dicarbonyl Compounds and Coumarins
  作者：Lu Yang、Jiang Zhu、Fukai Xie、Xiaoshi Peng、Bin Lin、Yongxiang Liu、Maosheng Cheng

  DOI：10.1134/s1070428019070236

  日期：2019.7

  environmentally friendly procedure was developed for the Knoevenagel condensation of aromatic aldehydes with diethyl malonate in the presence of FeCl3 and N-fluorobenzenesulfonimide as a source of electrophilic fluorine under solvent-free conditions. The scope of the reaction was explored using commercially available substrates. The reaction with substituted salicylaldehydes afforded the corresponding coumarin derivatives

  在无溶剂条件下，在FeCl 3和N-氟苯磺酰亚胺作为亲电子氟源的情况下，开发了一种高度环保的方法，用于芳族醛与丙二酸二乙酯的Knoevenagel缩合反应。使用可商购的底物探索反应的范围。与取代的水杨醛的反应提供了相应的香豆素衍生物，由于其潜在的医学重要性，它们引起了人们的兴趣。
• Fl-Ghaffar, Nahed F. Abd, Egyptian Journal of Chemistry, 2007, vol. 50, # 5, p. 691 - 698
  作者：Fl-Ghaffar, Nahed F. Abd

  DOI：——

  日期：——
• Aryne Precursors for Selective Generation of 3-Haloarynes: Preparation and Application to Synthetic Reactions
  作者：Eito Yoshioka、Kengo Kakigi、Shouta Miyoshi、Yuichi Kawasaki、Hideto Miyabe

  DOI：10.1021/acs.joc.0c01669

  日期：2020.11.6

  remarkable feature of new precursors is the selective generation of 3-haloarynes by suppressing the competitive thia-Fries rearrangement, which is the problem in the reaction using the well-known 3-haloaryne precursors. The advantage of new precursor 2a over a typical precursor 1 was confirmed by the direct comparisons in several reactions. The application of precursors 2a–2h to the syntheses of heterocycles

  研究了新的3-卤代芳烃前体2a-2h的合成和反应。的邻- （三甲基硅烷基）三氟甲磺酸的芳基的前体2A-2H是通过涉及一个简单的程序来制备ö -trimethylsilylation和三甲基甲硅烷基，随后三氟甲磺酸化的迁移。新的前体的显着特征是通过抑制竞争性的硫-弗里斯重排选择性地生成了3-卤代芳烃，这是使用众所周知的3-卤代芳烃前体的反应问题。通过在几个反应中的直接比较，证实了新的前体2a优于典型的前体1。前体2a–2h的应用 还报道了杂环的合成。
• 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.