4-(4-氟苯基)-1,2-二氢-2-氧代-3-喹啉羧酸乙酯 | 130954-99-3

• 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
• 中文名称: 4-(4-氟苯基)-1,2-二氢-2-氧代-3-喹啉羧酸乙酯
• 英文名称: ethyl 4-(4-fluorophenyl)-1,2-dihydro-2-oxo-3-quinolinecarboxylate
• 英文别名: ethyl 4-(4-fluorophenyl)-2-oxo-1H-quinoline-3-carboxylate
• CAS: 130954-99-3
• 化学式: C₁₈H₁₄FNO₃
• 分子量: 311.312
• InChiKey: SGZJHASWBLAEKI-UHFFFAOYSA-N

物化性质

• 熔点：
  204-205 °C
• 沸点：
  491.4±45.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-氟苯基)-1,2-二氢-2-氧代-3-喹啉羧酸乙酯 在 三氯氧磷 作用下， 反应 1.0h， 以98%的产率得到2-氯-4-(4-氟苯基)喹啉-3-羧酸乙酯
  参考文献：
  名称：

  胆固醇生物合成抑制剂。4.反式-6- [2-（取代的喹啉基）乙烯基/乙基]四氢-4-羟基-2H-吡喃-2-酮，一种新型的HMG-CoA还原酶抑制剂。

  摘要：

  制备了一系列取代的喹啉甲戊内酯，并评估了它们在体外和体内（胆固醇生物合成）抑制HMG-CoA还原酶的能力。由于先前的研究表明4-（4-氟苯基）和2-（1-甲基乙基）取代基具有最佳效价，因此将注意力集中在喹啉环的6位上。对带有多种6-取代基的少量类似物的生物学评估表明，在此位置进行修饰对效价影响很小。鉴定了几种化合物（8b，8e和11），它们在体外和体内试验中均显示出与Compactin和mevinolin相当的效价。

  DOI：

  10.1021/jm00105a057
• 作为产物：
  描述：

  丙二酸二乙酯 在 ammonium peroxydisulfate 、 rose bengal 、 铁粉 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 50.0h， 生成 4-(4-氟苯基)-1,2-二氢-2-氧代-3-喹啉羧酸乙酯
  参考文献：
  名称：

  Visible Light‐Induced Metal‐free Arylation of Coumarin‐3‐carboxylates with Arylboronic Acids

  摘要：

  The present work represents a novel methodology for the selective arylation of coumarin‐3‐carboxylates with arylboronic acids via a photochemical route, marking the first‐ever attempt for the direct alkenyl C−H arylation using rose bengal as a photocatalyst, which is a readily available and cost‐effective alternative to transition metal catalysis. The reaction proceeds smoothly in MeOH/H₂O solvent media in the presence of radical initiator affording the arylated products in good yields (60–80 %). The reaction parameters such as visible light, radical initiator, oxidant, anhydrous solvent, and inert atmosphere play a crucial role for the success of this methodology. The substituents present on the substrate show a significant effect on the conversion. This study provides a valuable contribution to the field of organic synthesis offering a new and efficient approach to the arylation of coumarin‐3‐carboxylic acid esters with a broad substrate scope and high functional group tolerance. It is a versatile method and provides a direct access to biologically relevant 4‐arylcoumarin‐3‐carboxylates.

  DOI：

  10.1002/asia.202400042

文献信息

• Inhibitors of cholesterol biosynthesis. 4. trans-6-[2-(Substituted-quinolinyl)ethenyl/ethyl]tetrahydro-4-hydroxy-2H-pyran-2-ones, a novel series of HMG-CoA reductase inhibitors
  作者：D. R. Sliskovic、J. A. Picard、W. H. Roark、B. D. Roth、E. Ferguson、B. R. Krause、R. S. Newton、C. Sekerke、M. K. Shaw

  DOI：10.1021/jm00105a057

  日期：1991.1

  A series of substituted quinoline mevalonolactones were prepared and evaluated for their ability to inhibit the enzyme HMG-CoA reductase both in vitro and (cholesterol biosynthesis) in vivo. Since previous studies suggested that the 4-(4-fluorophenyl) and 2-(1-methylethyl) substituents afforded optimum potency, attention was focused on variations at position 6 of the quinoline ring. Biological evaluation

  制备了一系列取代的喹啉甲戊内酯，并评估了它们在体外和体内（胆固醇生物合成）抑制HMG-CoA还原酶的能力。由于先前的研究表明4-（4-氟苯基）和2-（1-甲基乙基）取代基具有最佳效价，因此将注意力集中在喹啉环的6位上。对带有多种6-取代基的少量类似物的生物学评估表明，在此位置进行修饰对效价影响很小。鉴定了几种化合物（8b，8e和11），它们在体外和体内试验中均显示出与Compactin和mevinolin相当的效价。
• 6-(2-(2-(Substituted amino)-3-quinolinyl) ethenyl and ethyl)
  申请人：Warner-Lambert Company

  公开号：US04923861A1

  公开（公告）日：1990-05-08

  Novel 6-[2-[2-(substituted amino)-3-quinolinyl]-ethenyl and ethyl]tetrahydro-4-hydroxypyran-2-ones and/or oxides and the corresponding dihydroxy ring opened acids and esters are described, as well as methods for the preparation and pharmaceutical compositions of same, which are useful as inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) and are thus useful hypolipidemic and hypocholesterolemic agents.

  本发明涉及6-[2-[2-(取代氨基)-3-喹啉基]-乙烯基和乙基]四氢-4-羟基吡喃-2-酮和/或氧化物以及相应的二羟基环开放酸和酯，以及其制备方法和制备的药物组合物。这些化合物可作为3-羟基-3-甲基戊二酰辅酶A还原酶（HMG-CoA还原酶）的抑制剂，因此可作为降血脂和降胆固醇剂使用。
• Microwave-assisted solvent-free synthesis of substituted 2-quinolones
  作者：Cheng-Sheng Jia、Ya-Wei Dong、Shu-Jiang Tu、Guan-Wu Wang

  DOI：10.1016/j.tet.2006.11.030

  日期：2007.1

  A rapid and efficient method for the preparation of a variety of substituted 2-quinolones has been developed through the reactions of o-aminoarylketones with ester compounds containing a reactive a-methylene moiety in the presence of a catalytic amount of cerium chloride heptahydrate under solvent-free conditions in high yields. The rate and yield of the reaction are considerably improved by employing microwave irradiation. (c) 2006 Elsevier Ltd. All rights reserved.
• SLISKOVIC, D. R.;PICARD, J. A.;ROARK, W. H.;ROTH, B. D.;FERGUSON, E.;KRAU+, J. MED. CHEM., 34,(1991) N, C. 367-373
  作者：SLISKOVIC, D. R.、PICARD, J. A.、ROARK, W. H.、ROTH, B. D.、FERGUSON, E.、KRAU+

  DOI：——

  日期：——
• PICARD, JOSEPH A.;SLISKOVIC, DRAGO R.
  作者：PICARD, JOSEPH A.、SLISKOVIC, DRAGO R.

  DOI：——

  日期：——