4-methyl-3(4H)-benzoquinolinone | 4594-74-5

• 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: 4-methyl-3(4H)-benzoquinolinone
• 英文别名: 4-methyl-3(4H)-benzo[f]quinolinone；4-methyl-4H-benzo[f]quinolin-3-one；4-Methyl-4H-benzo[f]chinolin-3-on；4-Methylbenzo[f]quinolin-3-one
• CAS: 4594-74-5
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: OQABPFHBESNIML-UHFFFAOYSA-N

物化性质

• 熔点：
  174.0-174.5 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  357.0±22.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-3(4H)-benzoquinolinone 在 五氯化磷 、 三氯氧磷 作用下， 生成 3-iodo-4-methyl-benzo[f]quinolinium; iodide
  参考文献：
  名称：

  CVIII.- ψ含吡啶或β-naphthaquinoline核-Cyanine染料

  摘要：

  DOI：

  10.1039/jr9310000777
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 mercury(II) oxide 作用下， 生成 4-methyl-3(4H)-benzoquinolinone
  参考文献：
  名称：

  Claus; Besseler, Journal fur praktische Chemie (Leipzig 1954), 1898, vol. <2> 57, p. 60

  摘要：

  DOI：

文献信息

• Biocatalytic and Chemo-Enzymatic Synthesis of Quinolines and 2-Quinolones by Monoamine Oxidase (MAO-N) and Horseradish Peroxidase (HRP) Biocatalysts
  作者：Haoyue Xiang、Salvatore Ferla、Carmine Varricchio、Andrea Brancale、Nicola L. Brown、Gary W. Black、Nicholas J. Turner、Daniele Castagnolo

  DOI：10.1021/acscatal.2c05902

  日期：2023.3.3

  oxidase (MAO-N) enzymes were used to effectively catalyze the biotransformation of THQs into the corresponding aromatic quinoline derivatives, while N-cyclopropyl-N-alkylanilines were converted into 2-quinolone compounds through a horseradish peroxidase (HRP)-catalyzed annulation/aromatization reaction followed by Fe-mediated oxidation.

  脂肪族N-杂环的氧化芳构化是制备多种杂芳族化合物的基本有机转化。尽管许多人尝试提高这种转化的效率和实用性，但大多数合成方法仍然需要有毒且昂贵的试剂以及恶劣的条件。在此，我们描述了将 1,2,3,4-四氢喹啉 (THQ) 和N-环丙基-N-烷基苯胺分别氧化成喹啉和 2-喹诺酮的两种酶促策略。利用全细胞和纯化的单胺氧化酶（MAO-N）有效催化THQ生物转化为相应的芳香族喹啉衍生物，而N-环丙基-N-烷基苯胺则通过辣根过氧化物酶（HRP）转化为2-喹诺酮化合物。 -催化环化/芳构化反应，然后进行铁介导的氧化。
• Relative reactivities of heteroaromatic cations toward ferricyanide ion oxidation
  作者：John W. Bunting、Dimitrios Stefanidis

  DOI：10.1021/jo00361a025

  日期：1986.5
• Novel Photoinduced Electorn Transfer-Initiated Cyclization of 1,2,4-Triazole-Substituted α-Dehydronaphthylalaninamides in the Presence of Triethylamine
  作者：Tadamitsu Sakurai、Kei Maekawa、Atsushi Tomoda、Tetsutaro Igarashi

  DOI：10.3987/com-08-s(f)53

  日期：——

  The irradiation of the title compounds [(Z)-1] in nitrogen-saturated methanol containing triethylamine (TEA) at room temperature was found to quantitatively afford 2(1H)-benzo/[f]quinolinone (2) and 3,4-dihydro-3-(3-methyl-5-substituted 1,2,4-triazol-4-yl)-2(1H)-benzo[f]quinolinone (3) derivatives, which were described as being formed via electron transfer from TEA to the excited-state (E)-1. Analysis of solvent and substituent effects on the composition ratio of 2 to 3 confirmed that this ratio is increased from 0.2 to 9.0 with an increase in the proton-donating ability and polarity of solvent as well as in the electron-withdrawing ability of substituent bonded to the triazole ring.
• Substituent Effects on the Electron Transfer-Initiated Photochemical Transformation of 1,2,4-Triazole-Substituted α-Dehydroarylalaninamides into 2(1H)-Quinolinone Derivatives
  作者：Tadamitsu Sakurai、Yuichi Yazawa、Minoru Suzuki、Tetsutaro Igarashi

  DOI：10.3987/com-09-s(s)55

  日期：——

  An investigation was undertaken to elucidate substituent effects on the photoreactivity of 1,2,4-triazole-substituted alpha-dehydroarylalaninamides [(Z)-1] as well as on the selectivity of 2(1H)-quinolinone derivatives (2) from a synthetic point of view. It was found that photoinduced electron transfer-initiated cyclization of (Z)-1 bearing a meta-substituted phenyl or a 4-substituted naphthalen-1-yl group in methanol proceeds with a moderate to good efficiency affording the corresponding product 2 in a selectivity ranging from 33 to 100%.
• Fischer,O., Chemische Berichte, 1899, vol. 32, p. 1306
  作者：Fischer,O.

  DOI：——

  日期：——