4-nitro-N-propyl-1,8-naphthalimide | 39061-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-nitro-N-propyl-1,8-naphthalimide
• 英文别名: 6-nitro-2-propyl-1H-benzo[de]isoquinoline-1,3(2H)-dione；6-nitro-2-propylbenzo[de]isoquinoline-1,3-dione
• CAS: 39061-38-6
• 化学式: C₁₅H₁₂N₂O₄
• 分子量: 284.271
• InChiKey: FNWAUAFXHBVVIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  4-nitro-N-propyl-1,8-naphthalimide 在 盐酸 、 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 生成 6-amino-2-propyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  1,8-萘酰亚胺衍生物作为尿苷二磷酸选择性探针的研究：合成，光学性质和体内成像应用

  摘要：

  开发了基于1、8-萘甲酰亚胺的探针1，用于荧光检测尿苷二磷酸（UDP）。探针1在溶剂系统（DMSO-H 2 O）中选择性识别超过其他结构相似核苷酸的UDP 。在所有测试目标中，仅添加UDP可使荧光增强约13倍。探针1是没有金属中心的第一个受体部分，只能通过有机配体和核苷酸碱基之间形成的多个H键识别UDP。此外，探针1表现出优异的细胞渗透性。UDP的荧光成像通过探头1在Hela细胞和秀丽隐杆线虫（秀丽隐杆线虫）展示了其作为UDP体内成像荧光传感器的潜力。

  DOI：

  10.1016/j.dyepig.2017.04.006
• 作为产物：
  描述：

  苊 在 sodium dichromate 、 硝酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 4-nitro-N-propyl-1,8-naphthalimide
  参考文献：
  名称：

  涤纶织物染色用萘酰亚胺衍生物单偶氮分散染料的合成与表征

  摘要：

  以萘酰亚胺为原料制备了一系列单偶氮分散染料。萘酰亚胺的4-氨基-N-甲基（或N-乙基、N-丙基、N-丁基）衍生物用作重氮组分，β-萘酚、N,N-二乙基-间甲苯胺和对氨基苯乙酮构成耦合组件。为此，将苊进行硝化，然后进行氧化、胺化、还原、重氮化、偶联等各种单元过程。将合成的单偶氮分散染料应用于当地生产的涤纶织物，并对其光学性能进行了研究。通过 DSC、FTIR、H-NMR 和 UV-vis 分析技术对各种中间体以及染料进行了表征。

  DOI：

  10.1002/jccs.200500071

文献信息

• Synthesis and Characterization of Some Monoazo Disperse Dyestuffs Based on Naphthalimide Derivatives for Dyeing of Polyester Fabrics
  作者：A. Khosravi、S. Moradian、K. Gharanjig、F. Afshar Taromi

  DOI：10.1002/jccs.200500071

  日期：2005.6

  A series of monoazo disperse dyestuffs derived from naphthalimide were prepared. 4-Amino-N-methyl (alternatively N-ethyl, N-propyl, N-butyl) derivatives of naphthalimide were utilised as the diazo components and β-naphthol, N,N-diethyl-m-toluidine, and p-aminoacetophenone constituted the coupling components. To this end, acenaphthene was nitrated and then various unit processes such as oxidation, amination

  以萘酰亚胺为原料制备了一系列单偶氮分散染料。萘酰亚胺的4-氨基-N-甲基（或N-乙基、N-丙基、N-丁基）衍生物用作重氮组分，β-萘酚、N,N-二乙基-间甲苯胺和对氨基苯乙酮构成耦合组件。为此，将苊进行硝化，然后进行氧化、胺化、还原、重氮化、偶联等各种单元过程。将合成的单偶氮分散染料应用于当地生产的涤纶织物，并对其光学性能进行了研究。通过 DSC、FTIR、H-NMR 和 UV-vis 分析技术对各种中间体以及染料进行了表征。
• A fluorescent probe capable of detecting H2S at submicromolar concentrations in cells
  作者：Weimin Xuan、Rong Pan、Yanting Cao、Kejian Liu、Wei Wang

  DOI：10.1039/c2cc35602c

  日期：——

  A new internal charge transfer (ICT) fluorescent probe for highly selective and sensitive monitoring of H2S has been developed. The design takes advantage of the facile reduction of non-fluorescent hydroxyamine naphthalimide by H2S to highly fluorescent amine naphthalimide. It has been demonstrated that the probe is able to detect H2S at submicromolar concentrations in cells.

  一种用于高选择性和高灵敏度监测 H2S 的新型内部电荷转移（ICT）荧光探针已经研制成功。该设计利用了非荧光羟胺萘二甲酰亚胺被 H2S 易还原成高荧光胺萘二甲酰亚胺的优势。实验证明，该探针能够检测细胞中亚摩尔浓度的 H2S。
• 1,8-Naphthalimide-based colorimetric and fluorescent sensor for recognition of GMP, TMP, and UMP and its application in in vivo imaging
  作者：Li Mei Zhang、Lin E. Guo、Xue Mei Li、Yong Gang Shi、Gao Fen Wu、Xiao Guang Xie、Ying Zhou、Qi Hua Zhao、Jun Feng Zhang

  DOI：10.1016/j.tetlet.2014.09.074

  日期：2014.10

  In this study, a series of 1,8-naphthalimide-based analogs were developed for fluorescence imaging of nucleotides in Caenorhabditis elegans. In DMSO, compound 1 proved to be an effective and selective colorimetric and fluorescent sensor for recognition of GMP, TMP, and UMP over other structurally similar nucleotides. Among all the tested nucleotides, only the addition of GMP, TMP, and UMP resulted in a fluorescence color change from blue to brown with a fluorescence enhancement of more than 600-fold, with the colorless solution turning brown. NMR spectroscopic titration, theoretical calculations, and spectral tests performed using various solvent compositions confirmed that compound 1 formed multiple hydrogen bonds with the related base groups in the nucleotide. Compound 1 demonstrated its utility as a fluorescent chemosensor for detecting GMP, TMP, and UMP in in vivo imaging of GMP, TMP, and UMP in C elegans. (C) 2014 Elsevier Ltd. All rights reserved.
• Efficient Sonochemical Synthesis of 3‐ and 4‐Electron Withdrawing Ring Substituted <i>N</i>‐Alkyl‐1,8‐naphthalimides from the Related Anhydrides
  作者：Eduardo Rezende Triboni、Pedro Berci Filho、Roberto Gomes de Souza Berlinck、Mario José Politi

  DOI：10.1081/scc-120037911

  日期：2004.12.31

  1,8-N-alkyl-naphthalimides substituted with electron withdrawing groups were readily prepared in high yields using ultrasound in aqueous media.
• Okazaki et al., Yuki Gosei Kagaku Kyokaishi, 1956, vol. 14, p. 455,457
  作者：Okazaki et al.

  DOI：——

  日期：——