2,4-diacetylquinoline | 21718-94-5

• 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: 2,4-diacetylquinoline
• 英文别名: 1-(2-acetylquinolin-4-yl)ethanone
• CAS: 21718-94-5
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: KUOROUHDUSCUJI-UHFFFAOYSA-N

物化性质

• 熔点：
  69 °C
• 沸点：
  388.4±27.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-diacetylquinoline 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 22.0h， 生成 (Z)-4-[2-((Z)-3-Carboxy-3-hydroxy-acryloyl)-quinolin-4-yl]-2-hydroxy-4-oxo-but-2-enoic acid
  参考文献：
  名称：

  Structure Activity of 3-Aryl-1,3-diketo-Containing Compounds as HIV-1 Integrase Inhibitors

  摘要：

  The 4-aryl-2-hydroxy-4-oxo-2-butenoic acids and their isosteric tetrazoles are among an emerging class of aryl beta-diketo (ADK)-based agents which exhibit potent inhibition of HIV-1 integrase (IN)-catalyzed strand transfer (ST) processes, while having much reduced potencies against X-processing (3'-P) reactions. In the current study, L-708,906 (10e) and 5CITEP (13b), which are two examples of ADK inhibitors that have been reported by Merck and Shionogi pharmaceutical companies, served as model ADK leads. Structural variations to both the "left" and "right" sides of these molecules were made in order to examine effects on HIV-1 integrase inhibitory potencies. It was found that a variety of groups could be introduced onto the left side aryl ring with maintenance of good ST inhibitory potency. However, introduction of carboxylic acid-containing substituents onto the left side aryl ring enhanced T-P inhibitory potency and reduced selectivity toward ST reactions. Although both L-708,906 and 5CITEP show potent inhibition of IN in biochemical assays, there is a disparity of antiviral activity in cellular assays using HIV-1-infected cells. Neither 5CITEP nor any other of the indolyl-containing inhibitors exhibit significant antiviral effects in cellular systems. Alternatively, consistent with literature reports, L-708,906 does provide antiviral protection at low micromolar concentrations. Interestingly, several analogues of L-708,906 with varied substituents on the left side aryl ring, while having good inhibitory potencies against IN in extracellular assays, are not antiviral in whole-cell systems.

  DOI：

  10.1021/jm020037p
• 作为产物：
  描述：

  喹啉 、 alkaline earth salt of/the/ methylsulfuric acid 在 dipotassium peroxodisulfate 、 对甲苯磺酸一水合物 作用下， 以38%的产率得到1-(喹啉-2-基)乙酮
  参考文献：
  名称：

  PEG-400杂芳烃的无金属CH甲基化和乙酰化

  摘要：

  从可再生和廉价来源产生甲基碳来源具有挑战性。在本文中，我们通过使用不同的起始原料调整反应条件，首次描述了在O 2和TsOH·H 2 O下使用PEG-400进行氮杂杂芳烃甲基化和乙酰化的新颖而有效的途径。当前协议的关键特征是在无金属条件下具有良好的官能团耐受性和广泛的底物范围的氧化性C–O和C–C键断裂。通过一锅法证明了所设计方法的潜在适用性，可用于合成中枢神经系统（CNS）抑制剂和抗惊厥药物分子。

  DOI：

  10.1039/d0gc01183e

文献信息

• Iron-Catalyzed Minisci Type Acetylation of <i>N</i> -Heteroarenes Mediated by CH(OEt)₃ /TBHP
  作者：A. Srinivasulu、B. Shantharjun、D. Vani、K. Chinna Ashalu、A. Mohd、J. Wencel-Delord、F. Colobert、K. Rajender Reddy

  DOI：10.1002/ejoc.201900033

  日期：2019.2.28

  Iron-catalyzed acetylation of electron deficient N-heteroarenes has been reported using triethylorthoformate as robust and inexpensive acetyl source. This new method is successfully applied for the acetylation of quinolines, isoquinoline, quinoxalines, arylpyridines, bipyridines, and benzothiazole.

  据报道，铁催化的缺电子 N-杂芳烃乙酰化使用原甲酸三乙酯作为稳定且廉价的乙酰源。这种新方法已成功应用于喹啉、异喹啉、喹喔啉、芳基吡啶、联吡啶和苯并噻唑的乙酰化反应。
• Metal-, Photocatalyst-, and Light-Free Minisci C–H Acetylation of N-Heteroarenes with Vinyl Ethers
  作者：Jianyang Dong、Jianhua Liu、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.1c01310

  日期：2021.6.4

  Herein, we report a mild, operationally simple method for Minisci C–H acetylation of N-heteroarenes using vinyl ethers as robust, inexpensive acetyl sources. The reactions do not require a conventional photocatalysis, electrocatalysis, metal catalysis, light activation, or high temperature. This method is thus significantly more sustainable than previously reported methods in terms of cost, reagent

  在此，我们报告了一种温和、操作简单的 N-杂芳烃 Minisci C-H 乙酰化方法，使用乙烯基醚作为稳定、廉价的乙酰基来源。该反应不需要传统的光催化、电催化、金属催化、光活化或高温。因此，在成本、试剂毒性和废物产生方面，这种方法比以前报道的方法更具可持续性。该协议有望从丰富的原料材料中获得医学相关分子。
• Compounds to treat hiv infection and aids
  申请人：Burke R Terrence

  公开号：US20060063938A1

  公开（公告）日：2006-03-23

  The present invention relates to compounds of formula I: useful HIV infection, AIDS, and other similar diseases. These compounds include inhibitors of the retroviral integrase enzyme that are useful in the treatment of HIV infection, AIDS, and other similar diseases characterized by integration of a retroviral genome into a host chromosome. The compounds of the invention are useful in pharmaceutical compositions and methods of treatment to reduce incorporation of a donor DNA into a receiving DNA.

  本发明涉及公式I的化合物：用于治疗HIV感染、艾滋病和其他类似疾病。这些化合物包括逆转录病毒整合酶酶抑制剂，可用于治疗HIV感染、艾滋病和其他类似疾病，其特征是逆转录病毒基因组整合到宿主染色体中。该发明的化合物在制药组合物和治疗方法中有用，以减少供体DNA并入接收DNA。
• Citterio, Attilio; Gentile, Anna; Serravalle, Marco, Journal of Chemical Research, Miniprint, 1982, # 10, p. 2801 - 2815
  作者：Citterio, Attilio、Gentile, Anna、Serravalle, Marco、Tinucci, Laura、Vismara, Elena

  DOI：——

  日期：——
• CITTERIO, A.;GENTILE, A.;SERRAVALLE, M.;TINUCCI, L.;VISMARA, E., J. CHEM. RES. MICROFICHE, 1982, N 10, 272-273
  作者：CITTERIO, A.、GENTILE, A.、SERRAVALLE, M.、TINUCCI, L.、VISMARA, E.

  DOI：——

  日期：——