6,7-dimethoxy-3-phenyl-quinolin-2-ol | 4970-01-8

• 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: 6,7-dimethoxy-3-phenyl-quinolin-2-ol
• 英文别名: 6,7-Dimethoxy-3-phenyl-chinolin-2-ol；3-Phenyl-6,7-dimethoxycarbostyril；6,7-dimethoxy-3-phenyl-1H-quinolin-2-one
• CAS: 4970-01-8
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: GNBHFIYPIPFEFV-UHFFFAOYSA-N

物化性质

• 熔点：
  260 °C
• 沸点：
  493.7±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  sodium phenylacetate 在 硫酸 、 氨 、 乙酸酐 、 iron(II) sulfate 作用下， 生成 6,7-dimethoxy-3-phenyl-quinolin-2-ol
  参考文献：
  名称：

  Pschorr; Buckow, Chemische Berichte, 1900, vol. 33, p. 1830

  摘要：

  DOI：

文献信息

• Intramolecular amidation — An efficient synthesis of 3-aryl-2-quinolinones
  作者：Yinggang Luo、Feiyan Tao、Yan Liu、Bogang Li、Guolin Zhang

  DOI：10.1139/v06-163

  日期：2006.12.1

  To reveal the scope of the syntheses of 3-aryl-2-quinolinones from 2-nitro-α-phenylcinnamic acids, the isomerization of (E)-2-amino-α-phenylcinnamic acids was studied. The results showed that (E)-2-amino-α-phenylcinnamic acids were isomerized to its (Z)-forms under sunlight in organic solvents. The reaction temperature and the functional groups at both phenyl rings have no effect on the isomerization of (E)-2-amino-α-phenylcinnamic acids and the following intramolecular spontaneous amidation of (Z)-2-amino-α-phenylcinnamic acids. Various 3-aryl-2-quinolinones prepared in high total yields indicated that the syntheses of 3-aryl-2-quinolinones from Perkin condensation products 2-nitro-α-phenylcinnamic acids via reduction, sunlight-induced isomerization of (E)-2-amino-α-phenylcinnamic acids, and the following intramolecular amidation is an efficient procedure. Key words: 3-aryl-2-quinolinones, isomerization, amidation.

  为了揭示从 2-硝基-α-苯基肉桂酸合成 3-芳基-2-喹啉酮的范围，研究了 (E)-2 氨基-α-苯基肉桂酸的异构化。结果表明，在有机溶剂中，(E)-2-氨基-α-苯基肉桂酸在阳光下异构化为其(Z)形式。反应温度和两个苯基环上的官能团对(E)-2-氨基-α-苯基肉桂酸的异构化和随后(Z)-2-氨基-α-苯基肉桂酸的分子内自发酰胺化没有影响。总产率高的各种 3-芳基-2-喹啉酮的制备表明，从 Perkin 缩合产物 2-硝基-α-苯基肉桂酸通过还原、日光诱导的 (E)-2- 氨基-α-苯基肉桂酸异构化和随后的分子内酰胺化合成 3-芳基-2-喹啉酮是一种高效的方法。关键字3-芳基-2-喹啉酮 异构化 氨基化
• Facile Synthesis of 3-Substituted and 1,3-Disubstituted Quinolin-2(1H)-ones from 2-Nitrobenzaldehydes
  作者：Kwanghee Koh Park、Jin Young Jung

  DOI：10.3987/com-05-10462

  日期：——
• Long-Wavelength-Absorbing and -Emitting Carbostyrils with High Fluorescence Quantum Yields
  作者：Georg Uray、Karlheinz S. Niederreiter、Ferdinand Belaj、Walter M. F. Fabian

  DOI：10.1002/(sici)1522-2675(19990908)82:9<1408::aid-hlca1408>3.0.co;2-q

  日期：1999.9.8

  Synthesis, absorption and fluorescence spectra, as well as quantum yields of a series of donor-acceptor-substituted carbostyrils (= quinolin-2(1H)-ones), are reported. Unprecedented strong absorption maxima (epsilon = 10000-20000) close to the visible spectrum, large Stokes shifts up to 130 nm, and quantum yields up to 0.7 are obtained with derivatives containing donor substituents at C(6) and C(7), and either one Ph substituent at C(3) or one CF3 residue at C(4). For analytical applications in biochemistry and medicine, N(1)-functionalization, or amidoacylation at C(3) in the case of the CF3 derivatives, is possible without a concomitant hypsochromic shift of their absorption and emission maxima. Semiempirical molecular-orbital calculations (AM1 for structures, ZINDO for electronic transition energies) prove to bit a suitable tool for the prediction of absorption properties of these compounds. The crystal-structure analysis of 6,7-dimethoxy-1-methyl-3-nitro-4-(trifluoromethyl)quinolin-2-(1H)-one (7) (C13H11F3N2O5, monoclinic, P2(1)/c, a = 12.372(2), b = 12.154(2), c = 10.119(2)Angstrom, beta = 112.95(2)degrees) shows that the NO2 group, squeezed between the CF3 and the C=O group, is oriented almost perpendicularly (87.8(4)degrees) to the ring plane. The intramolecular F ... N distance between the CF3 and the NO2 group is only 2.513(4)Angstrom.
• Pschorr; Buckow, Chemische Berichte, 1900, vol. 33, p. 1830
  作者：Pschorr、Buckow

  DOI：——

  日期：——