2-methoxy-10-phenylacridin-9(10H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-methoxy-10-phenylacridin-9(10H)-one
• 英文别名: 2-methoxy-N-phenyl-9-acridinone；2-Methoxy-10-phenylacridin-9-one
• 化学式: C₂₀H₁₅NO₂
• 分子量: 301.345
• InChiKey: KBWBUBLEIZEBRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 硫酸 、 铜 、 potassium carbonate 作用下， 以 硝基苯 为溶剂， 反应 10.0h， 生成 2-methoxy-10-phenylacridin-9(10H)-one
  参考文献：
  名称：

  Thermal and Chemiluminescent Property of Dioxetanes Having an N-Arylacridane Structure

  摘要：

  Novel dioxetanes having an N-arylacridane structure were syn thesized. Studies on thermal stability and chemiluminescent property of these compounds showed that the aryl group cannot stabilize the dioxetane structure so much but can trigger the chemiluminescence by formation of the phenoxy anion.

  DOI：

  10.3987/com-97-s(n)85

文献信息

• 2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities
  作者：Sarah Zeghada、Ghenia Bentabed-Ababsa、Olivier Mongin、William Erb、Laurent Picot、Valérie Thiéry、Thierry Roisnel、Vincent Dorcet、Florence Mongin

  DOI：10.1016/j.tet.2020.131435

  日期：2020.9

  By starting from a common substrate, 2-aminobenzaldehyde, both acridines and acridones were prepared. The former were generated in high yields by copper-catalyzed N-arylation followed by acid-mediated cyclization while the latter were obtained by double copper-catalyzed N-arylation followed by cyclization under the same reaction conditions. Moreover, acridine was subjected to deprotometalation by recourse

  从共同的底物2-氨基苯甲醛开始，制备了cr啶和a啶酮。前者是通过铜催化的N-芳基化反应，然后进行酸介导的环化反应而以高收率产生的，而后者是通过双重铜催化的N-芳基化，然后在相同反应条件下环化。此外，a啶通过依赖于锂锌碱进行去金属化并转化为相应的4-碘衍生物，其与吡咯烷酮和吡唑参与铜催化的偶联。最后，将吡唑，吲哚和咔唑添加到裸a啶的9位上得到改善。虽然在黑素瘤细胞生长抑制中注意到了适度的生物学活性，但新制备的化合物具有有趣的光物理性质，这些性质在初步研究中已进行了评估。
• Electroluminescent (EL) devices
  申请人：Xerox Corporation

  公开号：US20030044646A1

  公开（公告）日：2003-03-06

  An electroluminescent device containing an anode, an organic electroluminescent element, and a cathode wherein the electroluminescent element contains, for example, a fluorescent hydrocarbon component of Formula (I) 1 wherein R 1 and R 2 are substituents, which are selected from the group consisting of hydrogen, an alkyl, an alicyclic alkyl, an alkoxy, a halogen, and a cyano; Ar 1 and Ar 2 are each independently an aromatic component or an aryl group comprised of a from about 4 to about 15 conjugate-bonded or fused benzene rings.

  一种电致发光装置，包含阳极、有机电致发光元件和阴极，其中电致发光元件包含例如式（I）中的荧光碳氢化合物组分，其中R1和R2是取代基，选自氢、烷基、脂环烷基、烷氧基、卤素和氰基的群；Ar1和Ar2分别是芳香组分或由约4至约15个共轭键合或螺合苯环组成的芳基基团。
• Base-Controlled Synthesis of Fluorescent Acridone Derivatives via Formal (4 + 2) Cycloaddition
  作者：Fa-Chuang Liu、Meng-Jie Si、Xin-Ru Shi、Shi-Yi Zhuang、Qun Cai、Yi Liu、An-Xin Wu

  DOI：10.1021/acs.joc.2c02977

  日期：2023.3.3

  of acridone derivatives has been developed from simple and easily accessible o-aminobenzamides and 2-(trimethylsilyl)aryl triflates. The base played an important role in the selective controlled synthesis of N-H and N-aryl acridones. A preliminary study on the fluorescence properties of N-aryl acridones demonstrated that they could be used as fluorescent materials with a broad emission range.

  从简单易得的邻氨基苯甲酰胺和 2-(三甲基甲硅烷基) 芳基三氟甲磺酸酯开发了一种用于直接组装吖啶酮衍生物的无过渡金属形式 (4 + 2) 环加成。该碱基在N -H和N-芳基吖啶酮的选择性可控合成中发挥了重要作用。对N-芳基吖啶酮荧光性质的初步研究表明，它们可以用作具有较宽发射范围的荧光材料。
• Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones
  作者：Yuesi Fang、Donald C. Rogness、Richard C. Larock、Feng Shi

  DOI：10.1021/jo3011073

  日期：2012.7.20

  N-Unsubstituted beta-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.
• Novel blue emitters for use in organic electroluminescence devices
  申请人：LG Display Co., Ltd.

  公开号：EP1580250B1

  公开（公告）日：2014-04-30