4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylic acid methyl ester | 223565-36-4

• 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: 4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylic acid methyl ester
• 英文别名: methyl 4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylate；methyl 4-oxo-2-phenyl-1H-quinoline-3-carboxylate
• CAS: 223565-36-4；816450-72-3
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: KLTNGKQVNDTSIE-UHFFFAOYSA-N

物化性质

• 熔点：
  175-178 °C
• 沸点：
  442.7±45.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylic acid methyl ester 在 氢氧化钾 作用下， 反应 3.0h， 生成 4-氧代-2-苯基-1H-喹啉-3-羧酸
  参考文献：
  名称：

  Synthesis of fluorinated 2-phenyl-4-quinolones from pyrrole-2,3-dionesElectronic supplementary information (ESI) available: spectroscopic data of compounds 5–11 (Tables S1–S3). See http://www.rsc.org/suppdata/p1/b2/b202128e/

  摘要：

  一系列取代的2-苯基-4-喹啉酮8-11通过对1-芳基-4-氰基-5-苯基吡咯-2,3-二酮7a-e和1-芳基-4-甲氧基羧基-5-苯基吡咯-2,3-二酮7f-j进行闪蒸真空热解(FVT)合成，产率良好。这些吡咯二酮7是由胺3与苯甲酮腈5a-e或甲基3-芳基氨基-3-苯基丙-2-烯酸酯5f-j反应得到的。

  DOI：

  10.1039/b202128e
• 作为产物：
  描述：

  二苯甲酮肟 在 三氟甲磺酸 、 trifluoromethanesulfonic acid anhydride 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.08h， 生成 4-oxo-2-phenyl-1,4-dihydroquinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Facile One-Pot Syntheses of Amidines and Enamines from Oximes via Beckmann Rearrangement Using Trifluoromethanesulfonic Anhydride

  摘要：

  通过将各种肟在甲苯中与三氟甲磺酸酐（Tf2O）和三乙胺反应，原位生成亚胺碳正中间体，并在温和条件下用胺或烯醇钠捕捉，得到相应的脒和烯胺。部分获得的烯胺随后通过分子内 Friedel-Crafts 酰基化反应转化为 2-取代的 4-氧代-3-喹啉羧酸衍生物。

  DOI：

  10.1246/bcsj.77.1717

文献信息

• Model Studies Related to Synthesis and 1,4-Dipolar Cycloaddition Reactions of Mesoionic Heterocycles
  作者：Yvette Abd El-Sayed Issac

  DOI：10.1246/bcsj.72.503

  日期：1999.3

  The reaction of 2-(substituted amino)pyridine with reactive malonic acid derivatives provided an extremely facile synthesis of the mesoionic compound 4-oxo-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olates. N,N′-Disubstituted amidine reacted with diethyl malonate to afford 4-quinolone in a one-pot cyclization and rearrangement (type A/I) of 4-oxopyridiniumolate 6. The latter compound was isolated via a reaction

  2-（取代氨基）吡啶与活性丙二酸衍生物的反应提供了一种极其容易合成的介离子化合物 4-oxo-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olates。N,N'-二取代脒与丙二酸二乙酯反应，在 4-氧代吡啶鎓酸酯 6 的一锅环化和重排（A/I 型）中得到 4-喹诺酮。通过无环脒与 AME 的反应分离后一种化合物。介离子嘧啶 6 与马来酸酐或 N-苯基马来酰亚胺的环加成反应产生 [2+4] 环加合物。三苯基吡咯并吡啶三酮 12 是通过环加合物 4-苄基-3,5-二氧代-1,2,6-三苯基-2,6-二氮杂双环 [2.2.2] 辛烷-7,8-二羧酸酐 11d 的环转化获得的。相比之下，环加合物 4-乙基衍生物 11c 和取代的 3,5-dioxo-1,2,6-triphenyl-2, 6-二氮杂双环[2.2.2]辛烷-7,8-二羧基N-苯基酰亚胺在相同反应条件下未得到12。研究了12的形成机理
• Regioselective Condensation of Alkylidenephosphoranes with Bifunctionalized Compounds: New Approach to the Synthesis of Fused<i>O</i>- and<i>N</i>-Heterocycles
  作者：Wafaa M. Abdou、Neven A. F. Ganoub、Amin F. M. Fahmy、Abeer A. M. Shaddy

  DOI：10.1080/104265090921092

  日期：2005.10

  A series of fused pyran- (similar to 40% yield) and furan- (similar to 20% yield) derivatives were regioselectively prepared from the reactions of 5,6-difur-2'y1-3-oxo-2,3-dihydropyridazin-4-carbonitrile with ester- and keto phosphorus ylides, whereas new ylides were obtained, in addition to fused furans, in almost equal yields (33%) from the reaction of the same substrate with cyanomethylene(triphenyl)phosphorane. However application of such Wittig reagents on 2[(benzylidene)amino]-benzonitrile afforded, in all cases, 4-hydroxyquinalines in a similar to 42% yield as major products. Moreover; 2-[(triphenylphosphoranylidene)amino] benzonitrile, with the corresponding alkene, was also isolated a side products.
• Switchable Access to 3-Carboxylate-4-quinolones and 1-Vinyl-3-carboxylate-4-quinolones via Oxidative Cyclization of Isatins and Alkynes
  作者：Shi-Fen Jiang、Cheng Xu、Zhi-Wen Zhou、Qin Zhang、Xiao-Hui Wen、Feng-Cheng Jia、An-Xin Wu

  DOI：10.1021/acs.orglett.8b01645

  日期：2018.7.20

  An efficient transition-metal-free oxidative cyclization reaction using isatins and alkynes for the facile synthesis of structurally diverse 4-quinolones has been developed. Intriguingly, switchable access to substituted 3-carboxylate-4-quinolones and 1-vinyl-3-carboxylate-4-quinolones could be achieved by choosing a different base in the reaction. The obtained products could undergo further transformations, increasing the application potential of the method in organic synthesis.
• Further Insight into the Reactivity of Oxazinones Toward Phosphorus Reagents
  作者：Wafaa M. Abdou、Azza A. Kamel、Maha D. Khidre

  DOI：10.1081/scc-200036592

  日期：2004.12.31

  A series of quinoline derivates has been obtained from the reaction of 3-phenyl-2,4-benzoxazin-1-one (1) with alkylidenephosphoranes. With ester ylides 3a,b, the reaction affords hydroxyquinolines 8a,b and new stable phosphorus ylide 9, whereas with keto ylides 3c,d, quinolinones 12a,b, hydroxyindoles 10a,b and benzoazepines 14a,b are obtained. 1 reacts with allyl-4, methyl-5a and ethyltriphenylphosphonium bromides 5b in the presence of LiH to afford 2-hydrophenyloxazolo[1,2-a]-4-hydroxyquinoline (16) from the first reaction whereas alkoxyquinolines 21a,b and hydroxyazepines 22a,b are obtained from 5a,b.
• Facile One-Pot Syntheses of Amidines and Enamines from Oximes via Beckmann Rearrangement Using Trifluoromethanesulfonic Anhydride
  作者：Tomofumi Takuwa、Tomofumi Minowa、Jim Yoshitaka Onishi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.77.1717

  日期：2004.9

  Iminocarbocation intermediates were in situ-generated by treating various oximes with trifluoromethanesulfonic anhydride (Tf2O) in the presence of triethylamine in toluene and nucleophilic trapping with amines or sodium enolates under mild conditions afforded the corresponding amidines and enamines. Some of the thus-obtained enamines were converted to 2-substituted 4-oxo-3-quinolinecarboxylic acid derivatives by subsequent intramolecular Friedel–Crafts acylation.

  通过将各种肟在甲苯中与三氟甲磺酸酐（Tf2O）和三乙胺反应，原位生成亚胺碳正中间体，并在温和条件下用胺或烯醇钠捕捉，得到相应的脒和烯胺。部分获得的烯胺随后通过分子内 Friedel-Crafts 酰基化反应转化为 2-取代的 4-氧代-3-喹啉羧酸衍生物。