7-methoxy-3-(2-thienyl)-2H-1-benzopyran-2-one | 676350-07-5

• 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: 7-methoxy-3-(2-thienyl)-2H-1-benzopyran-2-one
• 英文别名: 7-methoxy-3-(thiophen-2-yl)-2H-chromen-2-one；7-methoxy-3-(thiophen-2-yl)coumarin；7-methoxy-3-thiophen-2-ylchromen-2-one
• CAS: 676350-07-5
• 化学式: C₁₄H₁₀O₃S
• 分子量: 258.298
• InChiKey: KPDCQGDQRCDXTP-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C
• 沸点：
  452.1±45.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 溶剂黄146 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 7-methoxy-3-(2-thienyl)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis, human monoamine oxidase inhibitory activity and molecular docking studies of 3-heteroarylcoumarin derivatives

  摘要：

  Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Series of 3-indolyl and 3-thiophenylcoumarins were synthesized and evaluated as inhibitors of the two human MAO isoforms, hMAO-A and hMAO-B. In general, the derivatives were found to be selective hMAO-B inhibitors with IC(50) values in the nanoMolar (nM) to microMolar (mu M) range. Docking experiments were carried out in order to compare the theoretical and experimental affinity of these compounds to the hMAO-B protein. According to our results, docking experiments could be an interesting approach to try to predict the activity of this class of coumarins against MAO-B receptors. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.033

文献信息

• Base-promoted synthesis of coumarins from salicylaldehydes and aryl-substituted 1,1-dibromo-1-alkenes under transition-metal-free conditions
  作者：Jianming Liu、Xin Zhang、Lijun Shi、Muwen Liu、Yuanyuan Yue、Fuwei Li、Kelei Zhuo

  DOI：10.1039/c4cc04377d

  日期：——

  Facile synthesis of coumarin via the tandem reaction of salicylaldehyde with aryl-substituted 1,1-dibromo-1-alkene was developed. This new protocol proceeds smoothly under mild and transition-metal-free conditions, it allows rapid access to coumarins containing various heteroatoms that are more difficult to prepare by traditional methods. Based on the isolated intermediate of 4-(diethylamino)-3-phenylchroman-2-one and detailed mechanistic studies, a credible tandem pathway was proposed.

  开发了一种简单的合成香豆素的方法，利用水杨醛与芳基取代的1,1-二溴-1-烯的串联反应。该新方法在温和且无过渡金属的条件下顺利进行，能够快速合成含有多种杂原子的香豆素，而这些香豆素通过传统方法更难制备。基于分离得到的中间体4-(二乙氨基)-3-苯基克罗莫酮和详细的机理研究，提出了一条可信的串联反应路径。
• [EN] ETHYNYL CONTAINING ELECTRON TRANSPORT AGENTS AND THEIR USE IN ORGANIC LUMINESCENT DEVICES<br/>[FR] AGENTS DE TRANSPORT D'ELECTRONS CONTENANT DE L'ETHYNYL ET LEUR UTILISATION DANS DES DISPOSITIFS LUMINESCENTS ORGANIQUES
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2004096783A1

  公开（公告）日：2004-11-11

  Compounds of formula (I), compositions, organic electronic devices, and methods for preparing organic electronic devices are described. The compounds of the invention contain at least two carbon-carbon triple bonds and a heteroaromatic ring E having at least one -C=N unit. The compounds can be used as electron transport agents in organic electronic devices such as organic electroluminescent devices.

  描述了式（I）的化合物、组合物、有机电子器件以及制备有机电子器件的方法。该发明的化合物至少含有两个碳-碳三键和一个具有至少一个-C=N基团的杂芳环E。这些化合物可用作有机电子器件中的电子传输剂，如有机电致发光器件。
• Electron transport agents for organic electronic devices
  申请人：3M Innovative Properties Company

  公开号：US20040214036A1

  公开（公告）日：2004-10-28

  Compounds and compositions are provided that can be used as electron transport agents in organic electronic devices such as organic electroluminescent devices. The compounds are non-polymeric and have an aromatic core conjugated to end capping groups. The aromatic core contains a phenylene group arylene or naphthalene group arylene having a pendant heteroaryl group that includes a —C═N— unit.

  提供了可用作有机电子器件（如有机电致发光器件）中电子传输剂的化合物和组合物。这些化合物不是聚合物，具有芳香性核心，与端基团共轭。芳香性核心包含一个苯基团芳基或萘基团芳基，具有包括一个—C═N—单元的侧链杂环基团。
• Ethynyl containing electron transport dyes and compositions
  申请人：——

  公开号：US20040214037A1

  公开（公告）日：2004-10-28

  Compounds, compositions, organic electronic devices, and methods for preparing organic electronic devices are described. The compounds of the invention contain at least two carbon-carbon triple bonds and a heteroaromatic ring having at least one —C═N— unit. The compounds can be used as electron transport agents in organic electronic devices such as organic electroluminescent devices.

  本发明涉及化合物、组合物、有机电子器件以及制备有机电子器件的方法。该发明的化合物含有至少两个碳-碳三重键和一个含有至少一个-C═N-单元的杂环芳香环。这些化合物可用作有机电子器件中的电子输运剂，如有机电致发光器件。
• ELECTROACTIVE POLYMERS
  申请人：Roberts R. Ralph

  公开号：US20060155106A1

  公开（公告）日：2006-07-13

  Electroactive polymeric arylenes and intermediates useful for making such polymers are disclosed. The present invention also provides electroactive compositions comprising the electroactive polymeric arylenes, organic electronic devices which comprise these polymers and compositions, and methods of fabricating these devices.

  本发明公开了用于制备电活性聚合物芳基化合物和中间体。本发明还提供了包括所述电活性聚合物芳基化合物的电活性组合物，包括这些聚合物和组合物的有机电子器件，以及制造这些器件的方法。