6-nitro-2-phenylbenzo[d,e]isoquinoline-1,3-dione | 42340-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-nitro-2-phenylbenzo[d,e]isoquinoline-1,3-dione
• 英文别名: 4-nitro-N-phenyl-1,8-naphthalic imide；4-nitro-N-phenyl-1,8-naphthalimide；N-phenyl-4-nitro-1,8-naphthalimide；6-nitro-2-phenyl-benzo[de]isoquinoline-1,3-dione；6-nitro-2-phenyl-benz[de]isoquinoline-1,3-dione；6-Nitro-2-phenyl-benz[de]isochinolin-1,3-dion；6-nitro-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione；6-nitro-2-phenylbenzo[de]isoquinoline-1,3-dione
• CAS: 42340-35-2
• 化学式: C₁₈H₁₀N₂O₄
• mdl: MFCD00193253
• 分子量: 318.288
• InChiKey: UKTYWLRUFLFRCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-nitro-2-phenylbenzo[d,e]isoquinoline-1,3-dione 在 盐酸 、 tin(II) chloride dihdyrate 、 硫酸 、 对甲苯磺酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 5,10,10-triphenylbenzo[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione
  参考文献：
  名称：

  Isomeric naphthalimides bearing pyran units: Insight into mutual relation between structure and photochromic properties

  摘要：

  Two novel isomeric photochromic naphthopyrans (1 and 2) containing naphthalimide moieties were prepared and studied. In the compound 1, O-atom of pyran cycle is at C-3 position of naphthalene ring, whereas, in compound 2, O-atom of pyran cycle is at C-4 position. In the compound 2 due to para-position O-atom of pyran photochrome cycle is involved into the conjugated naphthalimide system. The variety in mutual position of pyran and naphthalimide units leads to remarkable difference in photochromic characteristics. Both compounds demonstrate the switching of the fluorescence by photoinduced conversion between the closed and open forms. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2015.02.004
• 作为产物：
  描述：

  苊 在 sodium dichromate 、 硝酸 、 溶剂黄146 作用下， 反应 1.5h， 生成 6-nitro-2-phenylbenzo[d,e]isoquinoline-1,3-dione
  参考文献：
  名称：

  Synthesis and spectral properties of 4-amino- and 4-acetylamino-N-arylnaphthalimides containing electron-donating groups in the N-aryl substituent

  摘要：

  本文描述了一种合成N-芳基取代的4-氨基和4-乙酰氨基萘酞亚胺衍生物的方法，这些衍生物在N-芳基取代基中具有单-和二烷氧基团或15-冠-5结构。向N-芳基片段的苯环中引入电子供体烷氧基团会导致萘酞亚胺生色团的荧光猝灭，这在N-乙酰基衍生物的光谱中最为明显。合成的4-氨基和4-乙酰氨基萘酞亚胺的光物理性质取决于溶剂的极性及其由于氢键形成的特定溶剂化能力。含冠醚的化合物有望作为金属阳离子的荧光化学传感器。

  DOI：

  10.1007/s11172-009-0160-x

文献信息

• Synthesis and spectral properties of 4-amino- and 4-acetylamino-N-arylnaphthalimides containing electron-donating groups in the N-aryl substituent
  作者：P. A. Panchenko、Yu. V. Fedorov、O. A. Fedorova、V. P. Perevalov、G. Jonusauskas

  DOI：10.1007/s11172-009-0160-x

  日期：2009.6

  A method for the synthesis of N-aryl-substituted 4-amino- and 4-acetylaminonaphthalimide derivatives with mono- and dialkoxy groups or a 15-crown-5 moiety in the N-aryl substituent is described. The introduction of electron-donating alkoxy groups into the benzene ring of the N-aryl fragment results in fluorescence quenching of the naphthalimide chromophore, which is most pronounced in the spectra of N-acetyl derivatives. The photophysical properties of the synthesized 4-amino- and 4-acetylaminonaphthalimides depend on the solvent polarity and its specific solvating ability due to H-bonding. The crown-containing compounds are promising fluorescent chemosensors for metal cations.

  本文描述了一种合成N-芳基取代的4-氨基和4-乙酰氨基萘酞亚胺衍生物的方法，这些衍生物在N-芳基取代基中具有单-和二烷氧基团或15-冠-5结构。向N-芳基片段的苯环中引入电子供体烷氧基团会导致萘酞亚胺生色团的荧光猝灭，这在N-乙酰基衍生物的光谱中最为明显。合成的4-氨基和4-乙酰氨基萘酞亚胺的光物理性质取决于溶剂的极性及其由于氢键形成的特定溶剂化能力。含冠醚的化合物有望作为金属阳离子的荧光化学传感器。
• 治疗β-地中海贫血和镰状细胞病的方法和组合物
  申请人：中央研究院

  公开号：CN105492428A

  公开（公告）日：2016-04-13

  治疗贫血(如β-地中海贫血和镰状性细胞贫血)的化合物、药物组合物和方法。
• METHODS AND COMPOSITIONS FOR TREATING BETA-THALASSEMIA AND SICKLE CELL DISEASE
  申请人：ACADEMIA SINICA

  公开号：US20160106728A1

  公开（公告）日：2016-04-21

  Compounds, pharmaceutical compositions, and methods for treating anemia β-thalassemia anemia or sickle cell anemia.

  化合物、药物组合和治疗贫血β-地中海贫血或镰状细胞贫血的方法。
• Synthesis and properties of fluorescent 1,8-naphthalimide dyes for application in liquid crystal displays
  作者：Ivo Grabchev、Ivanka Moneva、Vladimir Bojinov、Sylvie Guittonneau

  DOI：10.1039/a909153j

  日期：——

  A series of highly fluorescent 1,8-naphthalimide derivatives having an N-allylamino group at position 4 of the aromatic structure have been synthesised, and some of their properties for application in liquid crystal displays have been determined. The optical properties of the new substances are studied both in organic solvents and in the nematic liquid crystal ZLI 1840. The utility of the dyes for colouring liquid crystal displays of the 'guest–host' type is discussed on the basis of their spectral properties (absorption and emission) and the effect that the dyes have upon the orientation order parameter 〈P2〉 and upon the phase-transition behaviour of the liquid crystal in surface-stabilised display cells.

  合成了一系列在芳香结构的4位上具有N-烯丙氨基的高荧光1,8-萘二甲酰亚胺衍生物，并确定了它们在液晶显示器中的一些应用性能。在有机溶剂和向列液晶 ZLI 1840 中研究了新物质的光学特性。根据染料的光谱特性讨论了“客-主”型液晶显示器着色的实用性（吸收和发射）以及染料对取向顺序参数以及表面稳定显示单元中液晶的相变行为的影响。
• Influence of the configuration of the amine nitrogen atom on the efficiency of fluorescence of 4-aminonaphthalimide derivatives
  作者：Yu. A. Mednykh、Yu. A. Manaev、V. V. Volchkov、B. M. Uzhinov

  DOI：10.1007/s11176-005-0091-7

  日期：2004.11

  The fluorescence properties of 4-aminonaphthalimide were studied in relation to the size of the heterocycle incorporating the amine nitrogen atom, the temperature, and the polarity of the medium. Increases in the temperature, polarity of the medium, and heterocycle size increase the efficiency of the nonradiative deactivation and insignificantly affect the fluorescence rate. The low efficiency of fluorescence

  研究了4-氨基萘二甲酰亚胺的荧光性质与掺有胺氮原子的杂环的大小，温度和介质的极性有关。温度，介质极性和杂环尺寸的增加会增加非辐射灭活的效率，并且对荧光速率的影响很小。4-氨基萘二甲酰亚胺在极性溶剂中的荧光效率低与形成非荧光电荷转移态有关。4-氨基萘二甲酰亚胺的荧光效率与胺氮原子的转化势垒直接相关，而后者又由杂环胺取代基的结构决定。