1-Trifluoracetylacetamino-naphthalin | 1701-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Trifluoracetylacetamino-naphthalin
• 英文别名: 4,4,4-trifluoro-N-naphthalen-1-yl-3-oxobutanamide
• CAS: 1701-08-2
• 化学式: C₁₄H₁₀F₃NO₂
• 分子量: 281.234
• InChiKey: LMGAKAUDOQDDDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Trifluoracetylacetamino-naphthalin 在 硫酸 作用下， 以 水 为溶剂， 生成 4-(trifluoromethyl)benzo[h]quinolin-2(1H)-one
  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：

  1-萘胺 、 三氟乙酰乙酸乙酯 反应 0.5h， 生成 1-Trifluoracetylacetamino-naphthalin
  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

文献信息

• 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.