4-hydroxy-N-phenyl-1,8-naphthalimide | 796-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-hydroxy-N-phenyl-1,8-naphthalimide
• 英文别名: 6-hydroxy-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione；6-hydroxy-2-phenyl-benzo[de]isoquinoline-1,3-dione；6-Hydroxy-2-phenylbenzo[de]isoquinoline-1,3-dione
• CAS: 796-04-3
• 化学式: C₁₈H₁₁NO₃
• 分子量: 289.29
• InChiKey: SPTYNSPRFVHFKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.61
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-N-phenyl-1,8-naphthalimide 在 aluminum oxide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Synthesis and Photochromism of Naphthopyrans Bearing Naphthalimide Chromophore: Predominant Thermal Reversibility in Color-Fading and Fluorescence Switch

  摘要：

  Two novel photochromic naphthopyrans containing naphthalimide moieties (Nip1 and Nip2) were studied in solution under flash photolysis conditions, exhibiting highly photochromic response, rapid thermal bleaching rate and good fatigue-resistance. Owing to the different N-substituted imide groups at the naphthalimide units, the thermal bleaching rate of Nip2 bearing phenyl on the naphthalimide unit is found to be approximately 2 times that of Nip1 bearing n-butyl, indicating that the photochromic properties can be modulated with introduction of different functional groups on the naphthalimide unit. In Nip1 and Nip2, the strong electron-withdrawing effect of the imide group incorporated at the naphthalimide moiety maintains several merits: (i) shifting absorption bands to longer wavelength, (ii) beneficial to an enhancement in the ratio of transoid-cis (TC) isomer and an increase in the transformation rate from transoid-trans (TT) to TC with respect to reference compound NP, and (iii) resulting in a preferable color bleaching rate and fading absolutely to their colorless state with thermal reversibility. As demonstrated in the system of NP, the slow transformation process from TT to TC might be the predominant dynamic step in thermal back process, leading to the residual color of NP being only faded to its original colorless state by visible light irradiation. The optical densities of colored forms for Nip1 and Nip2 are dependent upon the intensity of incident light, ensuring a possible application in the manufacture of ophthalmic lenses and smart windows. Moreover, the fluorescence of Nip1 and Nip2 can be switched on and off by photoinduced conversion between the closed and open forms.

  DOI：

  10.1021/jp208082w
• 作为产物：
  描述：

  6-bromo-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 氢碘酸 、 copper(II) sulfate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 4-hydroxy-N-phenyl-1,8-naphthalimide
  参考文献：
  名称：

  萘酰亚胺基席夫碱衍生物及其制备方法和应用

  摘要：

  本发明公开了一种萘酰亚胺基席夫碱衍生物及其制备方法和应用。该萘酰亚胺基席夫碱衍生物的结构式为：#imgabs0#其中，R1、R2、R3和R4分别独立地为H或碳数为1‑4的烷基。该萘酰亚胺基席夫碱衍生物可以提高席夫碱酮式异构体的发光强度，从而将其作为静态体三维的显示介质，可以提高光束寻址产生的体素点的发光强度。

  公开号：

  CN118084785A

文献信息

• Cobalt(<scp>ii</scp>)-catalyzed <i>peri</i>-C(sp²)–H selective hydroxylation of naphthalene monoimides
  作者：Tapasi Chand、Princi Gupta、Nehali Oza、Manmohan Kapur

  DOI：10.1039/d3cc06050k

  日期：——

  Reported herein is an efficient and eco-friendly peri-selective monohydroxylation of naphthalene monoimides (NMIs) to access 4-hydroxy NMIs, which possess multidisciplinary applications.

  本文报告了一种高效、环保的萘一亚胺（NMIs）过选择性单羟基化反应，以获得具有多学科应用价值的 4-羟基 NMIs。
• Synthesis and study of the sensory properties of bichromophoric systems based on 1,8-naphthalimide and styrylpyridine, containing an oligoglycolic receptor fragment
  作者：P. A. Panchenko、A. E. Saifutiarova、M. I. Ivanova、A. S. Polyakova、Yu. V. Fedorov、O. A. Fedorova

  DOI：10.1007/s11172-024-4199-5

  日期：2024.4

  efficiency of resonance energy transfer in the system, and an increase in the intensity of the fluorescence band of the naphthalimide residue. Complexation led to a hypsofluoric shift of the maximum in the fluorescence spectrum of the “symmetric” bis(styryl-pyridine). In both cases, spectral changes made it possible to register a ratiometric fluorescent response to the presence of metal cations in the

  获得了萘二甲酰亚胺-苯乙烯基吡啶-、苯乙烯基吡啶-苯乙烯基吡啶-和萘二甲酰亚胺-萘二甲酰亚胺型金属阳离子双发色化学传感器。它们的光活性片段通过开链低聚乙二醇间隔基连接，该间隔基充当受体基团。光学和核磁共振光谱表明这些化合物可以在乙腈溶液中与钙和钡阳离子形成络合物。在“不对称”双发色团的情况下，这些阳离子的结合伴随着苯乙烯基吡啶的吸收带和发射带的红移、系统中共振能量转移效率的降低以及共振强度的增加。萘酰亚胺残基的荧光带。络合导致“对称”双（苯乙烯基-吡啶）荧光光谱中最大值的低荧光位移。在这两种情况下，光谱变化使得能够记录对溶液中金属阳离子存在的比率荧光响应。
• Synthesis of N -substituted 4-hydroxynaphthalimides using palladium-catalysed hydroxylation
  作者：Cassandra L. Fleming、Tim D. Nalder、Egan H. Doeven、Colin J. Barrow、Frederick M. Pfeffer、Trent D. Ashton

  DOI：10.1016/j.dyepig.2015.11.007

  日期：2016.3

  Successful implementation of a palladium-mediated hydroxylation of N-substituted 4-chloro-1,8-naphthalimides has been achieved. The methodology detailed herein utilises 4-chloro-1,8-naphthalic anhydride as a starting point and implements the catalyst/ligand combination of Pd(OAc)(2)/t-BuXPhos; all of which are relatively inexpensive. A range of imide substituents tolerated the reaction conditions, including acid sensitive substrates which are not compatible with other existing methodology. As such this approach is not only complimentary to existing procedures, it presents a more direct alternative to accessing 4-hydroxy-1,8-naphthalimides. (C) 2015 Elsevier Ltd. All rights reserved.
• Isomeric naphthalimides bearing pyran units: Insight into mutual relation between structure and photochromic properties
  作者：O.A. Fedorova、A.N. Sergeeva、P.A. Panchenko、Yu. V. Fedorov、F.G. Erko、J. Berthet、S. Delbaere

  DOI：10.1016/j.jphotochem.2015.02.004

  日期：2015.4

  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.