67823-52-3

Usage

InChI:InChI=1/C13H9N3/c14-16-15-11-5-6-13-10(8-11)7-9-3-1-2-4-12(9)13/h1-6,8H,7H2

Upstream product

• 153-78-6 2-aminofluorene 

Downstream Products

• 38179-90-7 N-(4-methylbenzyl)-9H-fluoren-2-amine 
• 82223-16-3 2-<4-Hydroxy-N-Benzyliden-amino>-fluoren 
• 13924-50-0 benzylidene-fluoren-2-yl-amine 
• 1262801-03-5 methyl N-9H-fluoren-2-yl-P-phenylphosphonamidate 
• 1169853-50-2 C₃₅H₂₄N₄O 
• 1169853-31-9 C₃₉H₃₃N₄O⁽¹⁺⁾*Cl^(1-) 
• 1169853-13-7 C₃₅H₂₃N₃O₂ 
• 73051-69-1 2-fluoren 

Relevant academic research and scientific papers

Transient resonance Raman and density functional theory investigation of the 2-fluorenylnitrenium ion

We report a transient resonance Raman spectrum for the 2-fluorenylnitrenium ion obtained after photolysis of 2-azidofluorene. The 10 experimental Raman band frequencies of the transient spectrum show very good agreement with the computed frequencies from BPW91/cc-PVDZ density functional theory calculations for the 2-fluorenylnitrenium ion. Our results confirm the assignment of the ～-460 nm transient absorption band formed after photolysis of 2-azidofluorene in water/acetonitrile or water solution to the singlet ground electronic state 2-fluorenylnitrenium ion. Our study indicates the 2-fluorenylnitrenium has a large degree of iminocyclohexadienyl cation character with significant delocalization of the charge over both phenyl rings of the fluorene moiety. We compare our results for the 2-fluoreneylnitrenium ion to those previously reported for several other arylnitrenium ions.

Time-resolved resonance Raman observation of the 2-fluorenylnitrenium ion reaction with guanosine to form a C8 intermediate

Time-resolved resonance Raman spectroscopy was used to directly observe the reaction of the 2-fluorenylnitrenium ion with guanosine to produce a C8 intermediate species. Comparison of the Raman spectra with results of density functional theory calculations indicates the C8 intermediate forms two CN conjugated bonds in ring 1 of the guanosine moiety. Copyright

Synthesis and studies on the photophysical/biophysical properties of triazolylfluorene-labeled 2′-deoxyuridines

The planar structure, attractive photophysical property, and scarcity of electronically conjugated fluorene-containing biomolecular building blocks have attracted recent research interest on synthesizing triazolylfluorene decorated nucleosides with modulated photophysical features. Herein, we report the synthesis of few fluorescent nucleosides wherein the C5 of 2′-deoxyuridine is electronically conjugated with fluorene analogues via Sonogashira cross-coupling and copper-catalyzed click reaction. The study of photophysical properties of the synthesized nucleosides shows that two of the synthesized nucleosides show interesting dual emission properties in various organic solvents. The dual emitting fluorene nucleosides might impact significantly in nucleic acid research for monitoring the DNA microenvironment. Furthermore, we evaluated the interaction of cyanofluorenyl 2′-deoxyuridine with Calf thymus DNA (ctDNA) and observed that this nucleoside could sense ctDNA via the generation of an enhanced fluorescence signal.

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

Stereospecific photochemistry of Δ2-1,2,3-triazolines in solution and in the solid state: Scope and mechanistic studies

The stereospecific photochemistry of ten N-aryl-substituted cis- or trans-Δ2-1,2,3-triazolines to form the corresponding cis- or trans-aziridines was investigated both in solution and in the solid-state. We found that photochemical reactions in the solid state are more stereospecific than in solution for the 8 crystalline Δ2-1,2,3-triazolines. Additionally, triplet sensitization for some triazolines results in triplet biradicals, which provide the more thermodynamically favored trans-aziridine regardless of the starting triazoline stereochemistry. Product analyses as a function of temperature and solvent polarity suggest that the electronic excitation of the Δ2-1,2,3-triazolines results in the formation of a 1,3-biradical intermediate.

Stereospecific Synthesis of Substituted Aziridines by a Crystal-to-Crystal Photodenitrogenation of δ2-1,2,3-Triazolines

Crystalline cis- or trans-δ2-1,2,3-triazolines prepared by highly stereospecific and regioselective hydrogen bonding-catalyzed dipolar cycloaddition of activated cis- or trans-alkenes with aryl azides undergo a highly stereospecific photodenitrogenation to form the corresponding cis- or trans- azidirines in high chemical yields. While examples involving disubstituted and trisubstituted triazolines highlight steric challenges encountered in the dipolar cycloaddition reaction, the stereochemical control exerted by the crystalline lattice is enhanced by bulky substituents in the triazoline precursors to generate aziridines photochemically.

Using click chemistry toward novel 1,2,3-triazole-linked dopamine D3 receptor ligands

The dopamine D3 receptor (D3R) is a target of pharmacotherapeutic interest in a variety of neurological disorders including schizophrenia, Parkinson's disease, restless leg syndrome, and drug addiction. A common molecular template used in the development of D3R-selective antagonists and partial agonists incorporates a butylamide linker between two pharmacophores, a phenylpiperazine moiety and an extended aryl ring system. The series of compounds described herein incorporates a change to that chemical template, replacing the amide functional group in the linker chain with a 1,2,3-triazole group. Although the amide linker in the 4-phenylpiperazine class of D3R ligands has been previously deemed critical for high D3R affinity and selectivity, the 1,2,3-triazole moiety serves as a suitable bioisosteric replacement and maintains desired D3R-binding functionality of the compounds. Additionally, using mouse liver microsomes to evaluate CYP450-mediated phase I metabolism, we determined that novel 1,2,3-triazole-containing compounds modestly improves metabolic stability compared to amide-containing analogues. The 1,2,3-triazole moiety allows for the modular attachment of chemical subunit libraries using copper-catalyzed azide-alkyne cycloaddition click chemistry, increasing the range of chemical entities that can be designed, synthesized, and developed toward D3R-selective therapeutic agents.

Synthesis of phosphonamidate peptides by Staudinger reactions of silylated phosphinic acids and esters

The Staudinger reaction of unprotected azido-peptides with silylated phosphinic acids and esters on the solid support offers a straightforward acid-free entry to different phosphonamidate peptide esters or acids under mild conditions in high purity and yield.

In situ "click" assembly of small molecule matrix metalloprotease inhibitors containing zinc-chelating groups

(Chemical Equation Presented) A panel of small molecule-based MMP inhibitors containing rhodanine warheads was assembled using "one-pot" click chemistry. Upon biological screening, moderate inhibitors were identified which specifically targets MMP-7 and MMP-13 over other MMPs.

Transient-resonance Raman and density functional theory investigation of 4-biphenylylnitrenium, 2-fluorenylnitrenium, and diphenylnitrenium ions

We present transient-resonance Raman spectra for the 4-biphenylylnitrenium, diphenylnitrenium, and 2-fluorenylnitrenium ions. These spectra display a number of fundamental vibrational bands whose frequencies exhibit good agreement with those computed usin