1(4H)-Quinolinecarboxylic acid, 4-oxo-, ethyl ester | 172538-82-8

• 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: 1(4H)-Quinolinecarboxylic acid, 4-oxo-, ethyl ester
• 英文别名: ethyl 4-oxoquinoline-1-carboxylate
• CAS: 172538-82-8
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: OLHNSBYARJRKSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1(4H)-Quinolinecarboxylic acid, 4-oxo-, ethyl ester 在 copper(l) iodide 、 三甲基氯硅烷 、 氧气 、 copper diacetate 、 sodium acetate 、 palladium diacetate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 ethyl 6,11-dioxo-6,11-dihydro-5H-indeno[2,1-b]quinoline-5-carboxylate
  参考文献：
  名称：

  Discovery of wrightiadione as a novel template for the TrkA kinase inhibitors

  摘要：

  Enzymatic kinase assays and docking simulation studies have shown that the natural product wrightiadione displays inhibitory activity toward TrkA and PLK3. In this study, the template of wrightiadione served as a starting point for Trk inhibitor development campaigns. Molecular simulation provided structural insights for the design of derivatives that were efficiently generated by our recently developed 3-step tandem synthetic approach, resulting in the discovery of compound 2h with biochemical potency at the single-digit micromolar level. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.070

文献信息

• A New Two-Step Synthesis of Quinolone Alkaloids Based on the Regioselective Addition of Organometallic Reagents to 4-Silyloxyquinolinium Triflates
  作者：Uwe Beifuss、Sabine Ledderhose

  DOI：10.1055/s-1997-758

  日期：1997.3

  Organolithium- as well as Grignard reagents regioselectively add to N-protected 4-silyloxyquinolinium triflates with yields ranging from 38 to 93 %; the Cbz-protected C-2 adducts are easily transformed in a single operation to give the corresponding 2-substituted 4-quinolones in nearly quantitative yields.

  有机锂试剂和格里尼亚试剂区域选择性地与N保护的4-硅氧基喹啉三氟甲磺酸酯反应，产率范围从38%到93%；Cbz保护的C-2加成产物可以在单一步骤中轻松转化为相应的2取代4-喹啉酮，几乎以定量的产率得到。
• 2-Aminobuta-1,3-dienes as annulation reagents for 4-quinolones and benzothiopyran-4-ones: an attractive route for the highly diastereoselective synthesis of acridine- and thioxanthene-derivatives
  作者：Uwe Beifuss、Michael Taraschewski

  DOI：10.1039/a704289b

  日期：——

  Enamines regioselectively add to the CN+-bond of 4-silyloxyquinolinium triflates with high yields, and the BF3·Et2O mediated annulations of 4-quinolones with 2-aminobuta-1,3-dienes proceed with high diastereoselectivity to give substituted 1,2,3,4,4a,9,9a,10-octahydroacridine-3,9-dione derivatives; 4-silyloxy-1-benzothiopyrylium triflates and benzothiopyran-4-ones behave analogously.

  烯胺能以高产率选择性地添加到 4-硅氧基喹啉鎓三氯酸盐的 CN+ 键上，BF3-Et2O 介导的 4-喹啉酮与 2-氨基丁-1,3-二烯的环化反应以高非对映选择性进行，从而得到取代的 1,2,3,4,4a,9,9a,10-八氢吖啶-3,9-二酮衍生物；4-silyloxy-1-benzothiopyrylium triflates 和苯并硫吡喃-4-酮的表现类似。
• The First Stereoselective Bifunctionalization of 4-Quinolones with Organometallics and <i>N</i>-Halosuccinimides to 2,3-<i>trans</i> Disubstituted Tetrahydroquinolones: Expected and Unexpected Results
  作者：Uwe Beifuss、Gerald Feder、Teresa Bes、Isabel Usón

  DOI：10.1055/s-1998-1724

  日期：1998.6

  The C-2-addition of organometallic reagents to 4-quinolones followed by reaction with N-halosuccinimides provides a short and diastereoselective entry for the preparation of 2,3-trans disubstituted tetrahydroquinolones.

  将有机金属试剂与 4-喹啉酮进行 C-2 加成，然后与 N-卤代丁二酰亚胺反应，为制备 2,3-反式二取代四氢喹啉酮提供了一个简捷和非对映选择性的途径。
• Efficient allylation of 4-silyloxyquinolinium triflates and other positively charged heteroaromatic systems
  作者：Uwe Beifuss、Ursula Schniske、Gerald Feder

  DOI：10.1016/s0040-4020(00)01066-8

  日期：2001.2

  The regioselective allylation of 4-silyloxyquinolinium triflates with allyltri-n-butyltin has been performed to give 2-allyl-4-silyloxy-1,2-dihydroquinolines with excellent yields. Similiar results have been obtained with 4-silyloxy-l-benzopyrylium triflates and 4-silyloxy-1-benzothiopyrylium triflates. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Tandem Dehydrogenation/Oxidation/Oxidative Cyclization Approach to Wrightiadione and Its Derivatives
  作者：Yujeong Jeong、Youngtaek Moon、Sungwoo Hong

  DOI：10.1021/acs.orglett.5b01618

  日期：2015.7.2

  Wrightiadione contains a unique tetracyclic isoflavone moiety and has been shown to exhibit a broad range of biological activities. An efficient and Straightforward synthetic method for generating the molecular complexity,of wrightiadione was developed, through three-step tandem dehydrogenation/oxidation/oxidative cyclization reactions with a Pd/Cu. catalytic system. This Unprecedented one-pot route utilizes a broad: range of substrates, providing a convenient and powerful synthetic tool for accessing naturally occurring tetracyclic isoflavone wrightiadione and its nitrogen-containing derivatives.