3-formyl-4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinoline | 65740-53-6

• 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: 3-formyl-4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinoline
• 英文别名: 4-hydroxy-3-formyl-1-phenyl-quinolin-2-one；1-Phenyl-3-Formyl-4-Hydroxy-2(1H)-Quinolinone；3-(Hydroxymethylidene)-1-phenylquinoline-2,4(1H,3H)-dione；4-hydroxy-2-oxo-1-phenylquinoline-3-carbaldehyde
• CAS: 65740-53-6
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: OAQKDDWJZDKCER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-formyl-4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinoline 在 硫酸 、 三氯氧磷 作用下， 反应 18.0h， 生成 4-氯-2-氧代-1-苯基喹啉-3-甲醛
  参考文献：
  名称：

  Nucleophilic Chlorination of 3-Formyl-4-hydroxy-quinolin-2(1H)-ones

  摘要：

  Chlorination of 1-substituted 3-formyl-4-hydroxy-2-quinolones (1a, b) with phosphorylchloride leads to 4-chloro-3-dichloromethylquinolones (2), which can be hydrolyzed to 4-chloro-3-formylquinolones (4). From the anilinomethylene quinolinediones (3), at low temperatures the formylquinolones 4 can be obtained directly, whereas at high temperatures cleavage of the tautomeric azomethine moiety followed by subsequent ring closure to the naphthyridines (7) takes place. With 1-unsubstituted 3-formyl-4-hydroxy-2-quinolones (1d) either the 3-dichloromethylquinolone (2d) or the 2,4-dichloro-3-dichloromethylquinoline (10) is obtained depending on the reaction conditions. Similar results are obtained with the 1-unsubstituted anilinomethylene compounds (3). Attempts to obtain the 3-formyl-2,4-dichloroquinoline (11) were unsuccessful because in all experiments the 2-chloro-group was converted to an oxygen function.

  DOI：

  10.1002/prac.19933350203
• 作为产物：
  描述：

  3-(anilinomethylidene)-1-phenylquinoline-2,4-dione 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以81%的产率得到3-formyl-4-hydroxy-2-oxo-1-phenyl-1,2-dihydroquinoline
  参考文献：
  名称：

  Nucleophilic Chlorination of 3-Formyl-4-hydroxy-quinolin-2(1H)-ones

  摘要：

  Chlorination of 1-substituted 3-formyl-4-hydroxy-2-quinolones (1a, b) with phosphorylchloride leads to 4-chloro-3-dichloromethylquinolones (2), which can be hydrolyzed to 4-chloro-3-formylquinolones (4). From the anilinomethylene quinolinediones (3), at low temperatures the formylquinolones 4 can be obtained directly, whereas at high temperatures cleavage of the tautomeric azomethine moiety followed by subsequent ring closure to the naphthyridines (7) takes place. With 1-unsubstituted 3-formyl-4-hydroxy-2-quinolones (1d) either the 3-dichloromethylquinolone (2d) or the 2,4-dichloro-3-dichloromethylquinoline (10) is obtained depending on the reaction conditions. Similar results are obtained with the 1-unsubstituted anilinomethylene compounds (3). Attempts to obtain the 3-formyl-2,4-dichloroquinoline (11) were unsuccessful because in all experiments the 2-chloro-group was converted to an oxygen function.

  DOI：

  10.1002/prac.19933350203

文献信息

• Synthesis and evaluation of molluscicidal and larvicidal activities of some novel enaminones derived from 4-hydroxyquinolinones: Part IX
  作者：Mohamed Abass、Bayaumy B. Mostafa

  DOI：10.1016/j.bmc.2005.06.038

  日期：2005.11

  series of 10 3-(hetarylaminomethylene)quinolinediones, 12 3-(substituted aminopropenoyl)-4-hydroxyquinolinones, and 10 3-(substituted aminomethylene-5-oxo-pyrazolinyl)-4-hydroxyquinolinones were synthesized as novel enaminones derived from 3-(un)substituted 4-hydroxyquinolin-2(1H)-ones in 72-94% yields and assayed for their molluscicidal activities against Biomphalaria alexandrina and Lymnaea natalensis

  合成了一系列的10个3-（杂芳基氨基亚甲基）喹啉二酮，12个3-（取代的氨基丙烯酰基）-4-羟基喹啉酮和10个3-（取代的氨基亚甲基-5-氧代吡唑啉基）-4-羟基喹啉酮，它们是由3-衍生而来的新型烯胺酮。 （un）取代的4-羟基喹啉-2（1H）-酮的产率为72-94％，并测定了它们对Biomphalaria alexandrina和Lymnaea natalensis蜗牛的杀软体动物活性。一些测试的烯胺酮具有很高的杀软体动物活性（LC（50）20ppm）。新化合物显示出了对亚历山大藻的卵孵化率，蜗牛的感染率和有效期更强的效力。此外，这些衍生物在减少接触时间的情况下显示出对曼氏血吸虫的水acid和尾c均具有潜在的杀幼虫作用（100％死亡率）。
• Synthesis and biological evaluation of some novel hetroaryl quinolinone derivatives
  作者：Ghada E. Abd El‐Ghani、Magdy A. El‐Sayed、El‐Sayed I. El‐Desoky

  DOI：10.1002/jhet.4424

  日期：2022.5

  quinoline (10) was utilized for the synthesis of 3-(([aryl]amino)methylene)-6-phenyl-2H-pyrano[3,2-c]quinoline-2,4,5 (3H,6H)-trione 11a-c via its treatment with three types of amines. Treatment of 1 with POCl3/Et3N afforded the corresponding 4-chloro derivative 20. Which upon treatment with thiourea lead to the formation of the corresponding 4-mercapto derivative 21. The latter 21 was alkylated using

  本研究的目的涉及合成含有喹啉部分的新型杂环支架，并研究它们作为抗菌剂的作用。4-羟基-6-苯基-2 H-吡喃并[3,2 - c ]喹啉-2,5(6 H ))-二酮( 1 )被用作构建新的多杂环系统的前体。它与三个芳基和（杂芳基）醛反应，得到相应的亚芳基2a - c。化合物2与水合肼发生亲核环化反应，得到吡唑基喹啉酮3。此外，1与 HCHO/吗啉的反应导致形成加合物7. 合成的N -(5–3-formyl-4-hydroxy-6-phenyl-2,5-dioxo-5,6-dihydro-2 H - pyrano [3,2 - c ] quinoline ( 10 ) 用于3-(([芳基]氨基)亚甲基)-6-苯基-2H-吡喃并[3,2 - c ]喹啉-2,4,5( 3H , 6H ) -三酮11a - c的合成用三种胺处理。用 POCl3/Et3N 处理 1 得到相应的 4-氯衍生物20。用硫脲处理后形成相应的
• Acyl and alkoxy substituted quinolines
  申请人：Schering Corporation

  公开号：US05378694A1

  公开（公告）日：1995-01-03

  Compounds useful as antiviral agents against DNA-containing viruses, such as herpes group viruses, are disclosed. The compounds are are represented by compounds of Formula 1.0: ##STR1## and their pharmaceutically acceptable salts and solvates. Pharmaceutical compositions containing compounds represented by Formula 1.0 and methods of treating a viral infection using compounds represented by Formula 1.0 are disclosed. Also disclosed are compounds useful as antihypertensive agents and methods of treating hypertension using such compounds. The antihypertensive agents are compounds represented by Formula 1.0 wherein R.sup.4 is selected from the group consisting of alkyl and aminoalkyl. Preferably R.sup.1 is H.

  本发明揭示了一些可用作抗DNA病毒（如疱疹病毒组）的抗病毒剂化合物。这些化合物由1.0式化合物表示：##STR1##以及它们的医药上可接受的盐和溶剂。本发明还揭示了含有1.0式化合物的药物组合物以及使用1.0式化合物治疗病毒感染的方法。此外，本发明还揭示了一些可用作降压剂的化合物以及使用这些化合物治疗高血压的方法。这些降压剂是由1.0式化合物表示的化合物，其中R.sup.4选自烷基和氨基烷基。最好R.sup.1是H。
• Gupta, M.C.L.N.; Rao, V. Sudhakar; Darbarwar, Malleshwar, Synthetic Communications, 1990, vol. 20, # 14, p. 2103 - 2111
  作者：Gupta, M.C.L.N.、Rao, V. Sudhakar、Darbarwar, Malleshwar

  DOI：——

  日期：——
• Gupta, M. C. L. N.; Darbarwar, Malleshwar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 11, p. 1080 - 1082
  作者：Gupta, M. C. L. N.、Darbarwar, Malleshwar

  DOI：——

  日期：——