6-N,N-dimethylamino-2,3-naphthalenedicarboxylic anhydride | 845255-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 6-N,N-dimethylamino-2,3-naphthalenedicarboxylic anhydride
• 英文别名: 6-(dimethylamino)-2,3-naphthalenedicarbocyclic anhydride；6-(dimethylamino)naphtho[2,3-c]furan-1,3-dione；6-(dimethylamino)benzo[f][2]benzofuran-1,3-dione
• CAS: 845255-77-8
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: ZZVAOWRXBFJIJR-UHFFFAOYSA-N

物化性质

• 沸点：
  458.3±20.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-N,N-dimethylamino-2,3-naphthalenedicarboxylic anhydride 在 水 作用下， 生成 6-N,N-dimethylamino-2,3-naphthalenedicarboxylic acid
  参考文献：
  名称：

  在受限的纳米腔中 仿生溶剂化6-（N，N-二甲基氨基）-2,3-萘酸酐的光谱研究†

  摘要：

  酶是生物催化剂，可以通过将其容纳在活性位点来极大地加快其反应速度。与没有催化剂的情况相比，由天然催化剂的活性位点提供的局部环境导致反应的显着速率提高。6-（N，N-UV-Vis和荧光光谱法在纯醇和仿生纳米大小的环境（例如表面活性剂，大环主体和蛋白质纳米腔）中使用UV-Vis和荧光光谱法研究了-二甲氨基）-2,3-萘酸酐探针。发现在醇中的溶剂分解速率直接由烷基链长调节，并且遵循阿累尼乌斯依赖性。在生理条件下（pH 7.4，在25°C下），探针在水中的水解速率非常慢。但是，在相同条件下，蛋白质和超分子纳米腔可以显着提高该速率。因此，对这种仿生溶剂分解理解的这种基本动力学分析将使我们能够设计出具有有效控释和功能的新型探针-药物偶联物。

  DOI：

  10.1039/c6cp08009j
• 作为产物：
  描述：

  6-N,N-dimethylamino-2,3-naphthalenedicarboxylic acid 在 乙酸酐 作用下， 反应 1.0h， 以90%的产率得到6-N,N-dimethylamino-2,3-naphthalenedicarboxylic anhydride
  参考文献：
  名称：

  Unusual large Stokes shift and solvatochromic fluorophore: Synthesis, spectra, and solvent effect of 6-substituted 2,3-naphthalimide

  摘要：

  In this article four new series of 6-substituted 2 3-naphthalimides (1a-d 2a-d 3a-d 4a-d and 4 e-h) have been designed and synthesized through the formation of key cyclic anhydride intermediate which was the precursor of the well known environment-sensitive fluorophore [6-N,N-dimethylammonaphthalimides (6-DMN)] and other 6-substituted 2 3-naphthalimide series (2 3 4) Based on 6-amino-2 3-naphthalimide (6-ANP) compound a new type of fluorophore was found to exhibit moderate to unusual large Stokes shift (297-303 nm) 6-ANP derivatives display relatively low fluorescence quantum yields in high polar protic solvents such as water (Phi(F) similar to 0 004 571-576 nm) and a significant unusual red shift due to (1) hydrogen bonding interaction of the excited state of the molecule with the solvents which presumably enhance the intersystem crossing process in the system to quench fluorescence (2) this large Stokes shift was assumed to be the consequence of a substantial change of the geometric structure from the ground state (S-0) to the first excited state (S-1)) Compared with the other compounds studied the fluorescence of the nitro- and halo-derivatives was rather weak probably due to the efficient intersystem crossing leading to a non-reactive triplet state (C) 2010 Elsevier B V All rights reserved

  DOI：

  10.1016/j.jphotochem.2010.09.002

文献信息

• Fluorescent probes for biological studies
  申请人：Imperiali Barbara

  公开号：US20060234206A1

  公开（公告）日：2006-10-19

  The present invention provides fluorescent compounds of formula (I) and methods monitoring protein-protein interactions.

  本发明提供了化合物的荧光化合物(I)的公式，并监测蛋白质相互作用的方法。
• FLUORESCENT PROBES FOR BIOLOGICAL STUDIES
  申请人：Imperiali Barbara

  公开号：US20090082577A1

  公开（公告）日：2009-03-26

  The present invention provides fluorescent compounds of formula (I) and methods monitoring protein-protein interactions.

  本发明提供了式(I)的荧光化合物和监测蛋白质相互作用的方法。
• Photophysics and Biological Applications of the Environment-Sensitive Fluorophore 6-<i>N</i>,<i>N</i>-Dimethylamino-2,3-naphthalimide
  作者：M. Eugenio Vázquez、Juan B. Blanco、B. Imperiali

  DOI：10.1021/ja0449168

  日期：2005.2.1

  We have synthesized a new environment-sensitive fluorophore, 6-N,N-dimethylamino-2,3-naphthalimide (6DMN). This chromophore exhibits valuable fluorescent properties as a biological probe with emission in the 500-600 nm range and a marked response to changes in the environment polarity. The 6DMN fluorescence is red-shifted in polar protic environments, with the maximum emission intensity shifting more than 100 nm from 491 nm in toluene to 592 nm in water. Additionally, the fluorescence quantum yield decreases more than 100-fold from chloroform (Phi = 0.225) to water (Phi = 0.002). The scope and applications of the 6DMN probe are expanded with the synthesis of an Fmoc-protected amino acid derivative (5), which contains the fluorophore. This unnatural amino acid has been introduced into several peptides, demonstrating that it can be manipulated under standard solid-phase peptide synthesis conditions. Peptides incorporating the new residue can be implemented for monitoring protein-protein interactions as exemplified in studies with Sire homology 2 (SH2) phosphotyrosine binding domains. The designed peptides exhibit a significant increase in the quantum yield of the long wavelength fluorescence emission band (596 nm) upon binding to selected SH2 domains (e.g., Crk SH2, Abl SH2, and PI3K SH2). The peptides can be used as ratiometric sensors, since the short wavelength band (460 nm) was found almost invariable throughout the titrations.
• US7442529B2
  申请人：——

  公开号：US7442529B2

  公开（公告）日：2008-10-28
• Unusual large Stokes shift and solvatochromic fluorophore: Synthesis, spectra, and solvent effect of 6-substituted 2,3-naphthalimide
  作者：Kishore Baathulaa、Yufang Xu、Xuhong Qian

  DOI：10.1016/j.jphotochem.2010.09.002

  日期：2010.11

  In this article four new series of 6-substituted 2 3-naphthalimides (1a-d 2a-d 3a-d 4a-d and 4 e-h) have been designed and synthesized through the formation of key cyclic anhydride intermediate which was the precursor of the well known environment-sensitive fluorophore [6-N,N-dimethylammonaphthalimides (6-DMN)] and other 6-substituted 2 3-naphthalimide series (2 3 4) Based on 6-amino-2 3-naphthalimide (6-ANP) compound a new type of fluorophore was found to exhibit moderate to unusual large Stokes shift (297-303 nm) 6-ANP derivatives display relatively low fluorescence quantum yields in high polar protic solvents such as water (Phi(F) similar to 0 004 571-576 nm) and a significant unusual red shift due to (1) hydrogen bonding interaction of the excited state of the molecule with the solvents which presumably enhance the intersystem crossing process in the system to quench fluorescence (2) this large Stokes shift was assumed to be the consequence of a substantial change of the geometric structure from the ground state (S-0) to the first excited state (S-1)) Compared with the other compounds studied the fluorescence of the nitro- and halo-derivatives was rather weak probably due to the efficient intersystem crossing leading to a non-reactive triplet state (C) 2010 Elsevier B V All rights reserved