3096-57-9

Usage

Uses

2-Amino-9-fluorenone is used as an active pharmaceutical intermediate.

InChI:InChI=1/C13H9NO/c14-8-5-6-10-9-3-1-2-4-11(9)13(15)12(10)7-8/h1-7H,14H2

Upstream product

• 3096-52-4 2-nitro-9H-fluoren-9-one 
• 3096-56-8 2-bromofluoren-9-one 
• 153-78-6 2-aminofluorene 
• 64-17-5 ethanol 
• 607-57-8 2-nitro-9H-fluorene 

Downstream Products

• 5416-86-4 N-(9-oxo-fluoren-2-yl)-succinamic acid 
• 33417-27-5 2-amino-9-hydroxyfluorene 
• 6949-73-1 2-hydroxyfluoren-9-one 
• 343-01-1 2-fluoro-9H-fluoren-9-one 
• 52086-09-6 2-amino-3-bromo-9-fluorenone 
• 88387-73-9 9-Oxo-2-amino-7-nitrofluorene 
• 42135-40-0 (9-oxo-fluoren-2-yl)-carbamic acid ethyl ester 
• 116702-84-2 2-(3-nitro-benzylidenamino)-fluoren-9-one 
• 116702-82-0 2-(4-nitro-benzylidenamino)-fluoren-9-one 
• 5454-42-2 2-Benzylidenamino-fluorenon 
• 82230-81-7 2-(4-hydroxy-benzylidenamino)-fluoren-9-one 
• 3405-11-6 3-Brom-2-N-propylamino-fluorenon 
• 3560-75-6 2-Ethoxycarbonylmethylamino-3-brom-fluorenon 
• 109471-74-1 2-(2-nitro-anilino)-fluoren-9-one 

Relevant academic research and scientific papers

Synthesis, structure and metal compounds of a novel chromophoric cyanamide ligand

The novel compound 2-cyanaminofluoren-9-one (HL) has been synthesized, and is readily deprotonated to form the corresponding cyanamide anion L-. This has been isolated as the Tl+L- and AsPh4+L- salts. The UV/visible spectra of HL and AsPh4+L- show the same amine to carbonyl charge transfer transition seen in other aminofluorenones, although at longer wavelengths. The compound AsPh4+L- undergoes the reversible one electron reduction typical of fluorenones, whilst HL undergoes an irreversible reduction. The crystal structure of AsPh4+L- was determined and related to the solvatochromic behaviour of the L- anion. Some simple EHMO calculations have been carried out on the L- anion of AsPh4+L-, which show the cyanamide based HOMO and carbonyl based LUMO involved in the aforementioned CT transition. The thallium salt Tl+L- has also been used as a transmetallating agent in reaction with trimethyltin chloride to produce the corresponding tin cyanamide complex [SnMe3L], and in reaction with (triphenylphosphine)gold chloride to produce the first reported gold cyanamide compound [AuL(PPh3)], whose crystal structure has been determined.

Palladated composite of Cu-BDC MOF and perlite as an efficient catalyst for hydrogenation of nitroarenes

A novel composite of metal-organic framework and perlite is prepared through hydrothermal treatment of terephthalic acid and Cu(NO3)2·3H2O in the presence of perlite. The resulting composite was then utilized as a support for the immobilization of Pd nanoparticles. The obtained compound was characterized via XRD, TGA, ICP, FTIR, TEM, FE-SEM/EDS and elemental mapping analysis and applied as a catalyst for the hydrogenation of nitroarenes under mild reaction condition. The results approved that the catalyst could efficiently promote hydrogenation of various nitroarenes with different electronic densities and steric properties. Moreover, the catalyst showed high selectivity towards hydrogenation of nitro groups. Hot filtration test affirmed heterogeneous nature of catalysis. Furthermore, the present catalytic composite was highly recyclable with low Pd leaching. A comparative study also approved superior activity of the composite compared to palladated perlite and metal-organic framework.

Efficient hydrogenation catalyst designing via preferential adsorption sites construction towards active copper

Based on the experimental and DFT calculation results, here for the first time we built preferential adsorption sites for nitroarenes by modification of the supported Cu catalysts surface with 1,10-phenathroline (1,10-phen), by which the yield of aniline via reduction of nitroarene is enhanced three times. Moreover, a macromolecular layer was in-situ generated on supported Cu catalysts to form a stable macromolecule modified supported Cu catalyst, i.e., CuAlOx-M. By applying the CuAlOx-M, a wide variety of nitroarene substrates react smoothly to afford the desired products in up to > 99% yield with > 99% selectivity. The method tolerates a variety of functional groups, including halides, ketone, amide, and C = C bond moieties. The excellent catalytic performance of the CuAlOx-M can be attributed to that the 1,10-phen modification benefits the preferential adsorption of nitrobenzene and slightly weakens adsorption of aniline on the supported nano-Cu surface.

Amphiphilic ligands for Cu-catalyzed aerobic oxidation to synthesize 9-fluorenones in water

A series of amphiphilic PEG-functionalized nitrogen ligands were developed for the highly efficient copper-catalyzed aerobic oxidation of 9-fluorenes, with molecular oxygen as the sole oxidant in neat water. A broad range of functional groups are well tolerated and thus offer the opportunity for further functionalization.

Method for synthesizing fluorenone ketone compound through molecular oxygen oxidation in water phase

Aiming at the technical problems that in the prior art a method for synthesizing a fluorenone ketone compound has organic solvent pollution and byproducts can be generated, the invention provides a method for synthesizing a fluorenone ketone compound through molecular oxygen oxidation in a water phase. The method comprises the following steps: by taking a fluorenone compound as a substrate, dispersing into an alkali solution, and at 40-120 DEG C, in the presence of oxygen, and with a water-soluble transition metal compound as a catalyst, stirring to carry out reactions, thereby obtaining the fluorenone ketone compound. By adopting the method, molecular oxygen is adopted as an oxidant, and water is adopted as a solvent, so that an organic solvent is avoided, and the problem that multiple byproducts are generated because of peroxidation can be avoided.

Hydrogenation of Functionalized Nitroarenes Catalyzed by Single-Phase Pyrite FeS2 Nanoparticles on N,S-Codoped Porous Carbon

Catalytic hydrogenation of nitroarenes is an industrially very important and environmentally friendly process for the production of anilines; however, highly chemoselective reduction of nitroarenes decorated with one or more reducible groups in a nitroarene molecule remains a challenge. Herein, a novel hybrid non-noble iron-based nanocatalyst (named as FeS2/NSC) was developed, which was prepared from biomass as C and N source together with inexpensive Fe(NO3)3 as Fe source through high-temperature pyrolysis in a straightforward and cost-effective procedure. Comprehensive characterization revealed that single-phase pyrite FeS2 nanoparticles with precisely defined composition and uniform size were homogeneously dispersed on N,S-codoped porous carbon with large specific surface area, hierarchical porous channels, and high pore volume. The resultant catalyst FeS2/NSC demonstrated good catalytic activity for hydrogenation of functionalized nitroarenes with good tolerance of various functional groups in water as a sustainable and green solvent. Compared with bulk pyrite FeS2 and other non-noble metal-based heterogeneous catalysts reported in the literature, a remarkably enhanced activity was observed under mild reaction conditions. More importantly, FeS2/NSC displayed exclusive chemoselectivity for the reduction of nitro groups for nitroarenes bearing varying readily reducible groups.

Transition-metal-free C(sp3)–H oxidation of diarylmethanes

An efficient direct C(sp3)–H oxidation of diarylmethanes has been demonstrated by this study. This method employs environment-friendly O2 as an oxidant and is promoted by commercially available MN(SiMe3)2 [M = K, Na or Li], which provides a facile method for the synthesis of various diaryl ketones in excellent yields. This protocol is metal-free, mild and compatible with a number of functional groups on substrates.

Improved synthetic method of 2-amino-9-fluorenone

The invention discloses an improved synthetic method of 2-amino-9-fluorenone. The improved synthetic method comprises the following steps: (1) adding dimethyl sulfoxide which is used as a solvent and 2-amino fluorine which is used as a solute into a reactor under an alkaline condition, and adding an oxidizing agent; (2) stirring for 1 hour to 5 days under a room temperature; (3) fractionally filtering, thus obtaining a brown solid 2-amino-9-fluorenone product. According to the improved synthetic method disclosed by the invention, the technical scheme is simple and economic, raw materials are easy to obtain, the preparation time is short, the yield is up to 98 percent, the content of byproducts is smaller than or equal to 2 percent, the improved synthetic method is particularly suitable for a pilot scale test and a large scale production of the 2-amino-9-fluorenone, and a good industrial application prospect is obtained.

With Wnt signal path to inhibit the active heterocyclic compounds (by machine translation)

The invention relates to a signal path with Wnt inhibiting activity of a heterocyclic compound, including the compound and its pharmaceutically acceptable salt, various isotope, various isomers or various crystal structure, having the general formula I of the structure shown in: the invention relates to a compound and its joint application composition can effectively inhibit the Wnt signal path, can be used for the treatment or prevention of a disorder associated with a Wnt signal path. (by machine translation)

NHC-Catalyzed Benzylic Csp3–H Bond Activation of Alkylarenes and N-Benzylamines for the Synthesis of 3H-Quinazolin-4-ones: Experimental and Theoretical Study

An N-heterocyclic carbene catalyzed benzylic Csp3–H bond activation of alkylarenes and N-benzylamines under metal-free conditions was developed. This organocatalyzed oxidative transformation afforded the corresponding carbonyl derivatives in good to excellent yields. A variety of alkylarenes and N-benzylamines were tolerated under the optimized reaction conditions. The established method was further extended to the synthesis of biologically important 3H-quinazolin-4-ones in good yields. For example, NPS 53574, a potent calcium receptor antagonist, was successfully synthesized by using this oxidative protocol. DFT studies show that the benzylic C–H bond activation proceeds through the nucleophilic attack of the free carbene on the benzylic carbon atom.