2-chloro-6,7-dimethoxy-3-phenylquinoline | 160953-96-8

• 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: 2-chloro-6,7-dimethoxy-3-phenylquinoline
• 英文别名: AG 1216
• CAS: 160953-96-8
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: JOYQLLBQXFUCSK-UHFFFAOYSA-N

物化性质

• 沸点：
  422.213±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.239±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-6,7-dimethoxy-3-phenylquinoline 在 溶剂黄146 作用下， 以 水 为溶剂， 以66%的产率得到6,7-dimethoxy-3-phenyl-quinolin-2-ol
  参考文献：
  名称：

  Long-Wavelength-Absorbing and -Emitting Carbostyrils with High Fluorescence Quantum Yields

  摘要：

  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.

  DOI：

  10.1002/(sici)1522-2675(19990908)82:9<1408::aid-hlca1408>3.0.co;2-q
• 作为产物：
  描述：

  N-(3,4-dimethoxyphenyl)-2-phenylacetamide 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 4.0h， 以96%的产率得到2-chloro-6,7-dimethoxy-3-phenylquinoline
  参考文献：
  名称：

  Tyrphostins。5.血小板衍生的生长因子受体酪氨酸激酶的有效抑制剂：喹喔啉，喹啉和吲哚酪氨酸受体抑制剂中的结构-活性关系。

  摘要：

  制备了一系列3-吲哚丙烯腈酪氨酸酪蛋白，2-氯-3-苯基喹啉和3-芳基喹喔啉，并测试了其对血小板衍生的生长因子受体酪氨酸激酶（PDGF-RTK）活性的抑制作用。发现抑制剂的效力为喹喔啉>喹啉>吲哚。喹喔啉和喹啉在6和7位上的亲脂基团（甲基，甲氧基）和3位上的苯基对于效价至关重要，而酪蛋白中的亲水邻苯二酚基团在不同位点具有抑制EGFR激酶活性。抑制剂对PDGF具有选择性，对EGF受体和HER-2 / c-ErbB-2受体无活性。

  DOI：

  10.1021/jm950727b

文献信息

• Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity
  作者：Nicolai A. Aksenov、Alexander V. Aksenov、Nikita K. Kirilov、Nikolai A. Arutiunov、Dmitrii A. Aksenov、Vladimir Maslivetc、Zhenze Zhao、Liqin Du、Michael Rubin、Alexander Kornienko

  DOI：10.1039/d0ob01007c

  日期：——

  2-hydrazinylquinolines, 2-hydrazinylpyridines and bis-2,4-dihydrazinylpyrimidines in polyphosphoric acid (PPA) affording 1,2,4-triazolo[4,3-a]quinolines, 1,2,4-triazolo[4,3-a]pyridines and bis[1,2,4]triazolo[4,3-a:4′,3′-c]pyrimidines, respectively. The reaction expands the scope of heterocyclic annulations involving phosphorylated nitronates, believed to be the electrophilic intermediates formed from nitroalkanes

  我们发现了硝基烷烃与 2-肼基喹啉、2-肼基吡啶和双 2,4-二肼基嘧啶在多磷酸 (PPA) 中的反应，得到 1,2,4-三唑并[4,3- a ]喹啉, 1,2,4 -三唑并[4,3- a ]吡啶和双[1,2,4]三唑并[4,3- a :4′,3′- c]嘧啶，分别。该反应扩大了涉及磷酸化硝酸盐的杂环环化的范围，被认为是由 PPA 中的硝基烷形成的亲电子中间体。几种合成的三唑类化合物通过诱导神经母细胞瘤癌细胞分化而显示出有希望的抗癌活性。由于迫切需要用于神经母细胞瘤治疗的新型分化剂，这一发现值得进一步评估这类化合物对神经母细胞瘤的治疗作用。
• Tyrphostins. 5. Potent Inhibitors of Platelet-Derived Growth Factor Receptor Tyrosine Kinase:  Structure−Activity Relationships in Quinoxalines, Quinolines, and Indole Tyrphostins
  作者：Aviv Gazit、Harald App、Gerald McMahon、Jefferey Chen、Alexander Levitzki、Frank D. Bohmer

  DOI：10.1021/jm950727b

  日期：1996.1.1

  3-arylquinoxalines were prepared and tested for inhibition of platelet-derived growth factor receptor tyrosine kinase (PDGF-RTK) activity. The potency of the inhibitors was found to be quinoxalines > quinolines > indoles. Lipophilic groups (methyl, methoxy) in the 6 and 7 positions and phenyl at the 3 position of quinoxalines and quinolines were essential for potency, in contrast to the hydrophilic catechol

  制备了一系列3-吲哚丙烯腈酪氨酸酪蛋白，2-氯-3-苯基喹啉和3-芳基喹喔啉，并测试了其对血小板衍生的生长因子受体酪氨酸激酶（PDGF-RTK）活性的抑制作用。发现抑制剂的效力为喹喔啉>喹啉>吲哚。喹喔啉和喹啉在6和7位上的亲脂基团（甲基，甲氧基）和3位上的苯基对于效价至关重要，而酪蛋白中的亲水邻苯二酚基团在不同位点具有抑制EGFR激酶活性。抑制剂对PDGF具有选择性，对EGF受体和HER-2 / c-ErbB-2受体无活性。
• 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.