4439-53-6

Usage

Uses

Used in Pharmaceutical Industry:
BENZYL-FURAN-2-YLMETHYL-AMINE is used as a building block for the synthesis of various pharmaceuticals and biologically active compounds due to its distinctive structure and potential pharmacological activity. Its presence in drug design can contribute to the development of new therapeutic agents.
Used in Organic Chemistry:
In the field of organic chemistry, BENZYL-FURAN-2-YLMETHYL-AMINE is utilized as an important intermediate in the production of a variety of organic compounds and materials. Its reactivity and chemical properties make it a versatile component in organic synthesis processes.

InChI:InChI=1/C12H13NO/c1-2-5-11(6-3-1)9-13-10-12-7-4-8-14-12/h1-8,13H,9-10H2

Upstream product

• 4393-11-7 N-benzyl-1-(furan-2-yl)methanimine 
• 617-89-0 furan-2-ylmethanamine 
• 100-52-7 benzaldehyde 
• 42882-50-8 N-benzylidene-1-(furan-2-yl)methylamine 
• 10354-48-0 furan-2-carboxylic acid benzylamide 
• 98-01-1 furfural 
• 100-46-9 benzylamine 
• 100-47-0 benzonitrile 
• 617-90-3 2-furancarbonitrile 
• 100-51-6 benzyl alcohol 
• 527-69-5 2-furancarbonyl chloride 
• 98-00-0 (2-furyl)methyl alcohol 
• 124-38-9 carbon dioxide 
• 22661-25-2 (Z)-N-(furan-2-ylmethylene)-1-phenylmethanamine oxide 

Downstream Products

• 100142-58-3 benzyl-furfuryl-nitroso-amine 
• 182358-24-3 6-(Benzyl-furan-2-ylmethyl-amino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 
• 182358-35-6 6-(Benzyl-furan-2-ylmethyl-amino)-1,3-dimethyl-5-(phenyl-hydrazonomethyl)-1H-pyrimidine-2,4-dione 
• 1212092-04-0 3-benzyl-4-oxo-10-oxa-3-azatricyclo[5.2.1.0*1,5*]dec-8-ene-6-carboxylic acid 
• 1390623-33-2 (S)-1-(2-benzyl-3-oxoisoindoline-4-carbonyl)pyrrolidine-2-carbonitrile 
• 1390623-34-3 ZIN⁽⁰³⁸⁾C₀₀₅₉₄ 

Relevant academic research and scientific papers

The 3F Library: Fluorinated Fsp3-Rich Fragments for Expeditious 19F NMR Based Screening

Fragment-based drug discovery (FBDD) is a popular method in academia and the pharmaceutical industry for the discovery of early lead candidates. Despite its wide-spread use, the approach still suffers from laborious screening workflows and a limited diversity in the fragments applied. Presented here is the design, synthesis, and biological evaluation of the first fragment library specifically tailored to tackle both these challenges. The 3F library of 115 fluorinated, Fsp3-rich fragments is shape diverse and natural-product-like with desirable physicochemical properties. The library is perfectly suited for rapid and efficient screening by NMR spectroscopy in a two-stage workflow of 19F NMR and subsequent 1H NMR methods. Hits against four diverse protein targets are widely distributed among the fragment scaffolds in the 3F library and a 67 % validation rate was achieved using secondary assays. This collection is the first synthetic fragment library tailor-made for 19F NMR screening and the results demonstrate that the approach should find broad application in the FBDD community.

Inter- and intramolecular diels-alder reaction of ethenetricarboxylate derivatives

Inter- and intramolecular [4+2] cycloaddition reactions of highly electron-deficient ethenetricarboxylates have been studied. Intermolecular Diels-Alder reaction of ethenetricarboxylate esters and cyclopentadiene proceeded at room temperature or -20 °C to give cycloadducts with 1:1.5-1.9 endo:exo ratio. Lewis acids such as EtAlCl2, Zn(OTf)2 and Cu(OTf)2 catalyzed reaction at room temperature or -40 °C gave cycloadducts with 3.1-5.4:1 endo:exo ratio. Reaction of N-benzyl- or N-allyl-2-furylmethylamine and 1,1-diethyl 2-hydrogen ethenetricarboxylate in the presence of EDCI/HOBt/Et3N at room temperature led directly to an intramolecular Diels-Alder adduct stereoselectively. The observed stereoselectivities were explained by the use of DFT calculations.

Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions

A simple and efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine-BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to 95%. The strategy was applied to the synthesis of 15N labeled in 89% yield.

Sulfated polyborate: A dual catalyst for the reductive amination of aldehydes and ketones by NaBH4

An efficient, quick, and environment-friendly one-pot reductive amination of aldehydes or ketones was developed. In ethanol at 70 °C, a imination catalyzed by sulfated polyborate and further reduced by sodium borohydride yields various amines. The present method has many significant benefits, including a shorter reaction time, excellent yields, and a hassle-free, straightforward experimental process. The reaction has a wide range of applications due to its flexibility, including secondary amine for reductive amination.

Selective butyryl cholinesterase inhibitor or pharmaceutically acceptable salt thereof as well as preparation method and application thereof

The invention discloses a selective butyryl cholinesterase inhibitor or a pharmaceutically acceptable salt thereof, and a preparation method and application thereof, wherein the inhibitor has the selective butyrylcholinesterase inhibitor of the general formula (I) or the formula (II) or a pharmaceutically acceptable salt thereof. The compound or the pharmaceutically acceptable salt thereof disclosed by the invention has good in-vitro target activity and extremely high selectivity, and can be used as a leader substance for further developing an anti-'s disease through selective inhibition of butyrylcholine esterase.

Preparation and synthesis method of aromatic amine compound with function of specifically inhibiting HIF-2alpha

The invention relates to a preparation method of an HIF-2alpha small-molecule inhibitor (2-((benzyl(furan-2-yl methyl) amino) methyl)-8-methyl-4H-pyrido[1, 2-a]pyrimidine-4-ketone). The compound is characterized in that 4-methylpyridine-2-amine is used as an initial raw material, and 2-chloro-8-methyl-4H-pyrido [1, 2-a] pyrimidine-4-ketone is obtained through condensation cyclization of 4-methylpyridine-2-amine and the compound, furfural is taken as an initial raw material, an addition reaction is carried out on the furfural and benzylamine to obtain N-furan benzylamine, and a N-alkylation reaction is carried out on the obtained 2-chloro-8-methyl-4H-pyrido[1, 2-a]pyrimidine-4-ketone and N-furan benzylamine to obtain the HIF-2alpha small-molecule inhibitor. The invention discloses the preparation method of the HIF-2alpha small-molecule inhibitor for the first time, the method has the advantages of few steps, simple operation, rapid reaction and no need of high pressure, the yield and purity of the prepared compound are high, and the raw materials are easy to obtain.

Preparation of HIF-2alpha small-molecule inhibitor and application thereof

The invention belongs to the technical field of medicines, and relates to an HIF-2 alpha small-molecule inhibitor as well as a preparation method and an application thereof. The HIF-2alpha small-molecule inhibitor is a compound as shown in a structural general formula I and a stereoisomer, a pharmaceutically acceptable salt, a hydrate, a solvate or a prodrug thereof. According to the invention, molecular simulation drug design software MOE is used for screening and molecular docking of pharmacophores, according to a final docking dominant structure and an isosteric principle, a series of compounds are designed and synthesized, and an in-vitro anti-tumor activity screening test shows that the compounds have anti-tumor activity. The HIF-2 alpha small-molecule inhibitor provided by the invention has a relatively good application prospect in the aspect of preventing or treating cancers, particularly glioma.

Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines

Treatment of salicylaldiminato ligand L1H-L2H (L1H = 2,4-di-tert-butyl-6-((quinolin-8-ylimino)methyl)phenol; L2H = 2,4-di-tert-butyl-6-(((2-(diethylamino)ethyl)imino)methyl)phenol) with Ni(OAc)2·4H2O in refluxing ethanol afforded nickel complexes [(L1)Ni(OAc)] (1) and [(L2)Ni(OAc)] (2), respectively. Reaction of L3H (L3H = (2,4-di-tert-butyl-6-(((2-(pyridin-2-yl)ethyl)imino)methyl)phenol)) with Ni(OAc)2·4H2O in the presence of excess triethylanmine gave the dual ligands coordinated nickel complex [(L2)2Ni] (3). Complexes 1-3 were well characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine derivatives by employing an earth-abundant nickel salt and easily prepared salicylaldiminato ligands.

Aluminum Metal-Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis

The development of chemoselective and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal-organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under mild conditions. The nickel-hydride catalyst was prepared by the metalation of aluminum hydroxide secondary building units (SBUs) of DUT-5 having the formula of Al(μ2-OH)(bpdc) (bpdc = 4,4′-biphenyldicarboxylate) with NiBr2 followed by a reaction with NaEt3BH. DUT-5-NiH has a broad substrate scope with excellent functional group tolerance in the hydrogenation of aromatic and aliphatic nitro and nitrile compounds under 1 bar H2 and could be recycled and reused at least 10 times. By changing the reaction conditions of the hydrogenation of nitriles, symmetric or unsymmetric secondary amines were also afforded selectively. The experimental and computational studies suggested reversible nitrile coordination to nickel followed by 1,2-insertion of coordinated nitrile into the nickel-hydride bond occurring in the turnover-limiting step. In addition, DUT-5-NiH is also an active catalyst for chemoselective hydrogenolysis of carbon-oxygen bonds in aryl ethers to afford hydrocarbons under atmospheric hydrogen in the absence of any base, which is important for the generation of fuels from biomass. This work highlights the potential of MOF-based single-site earth-abundant metal catalysts for practical and eco-friendly production of chemical feedstocks and biofuels.

Polyoxometalate-Driven Ease Conversion of Valuable Furfural to trans- N, N-4,5-Diaminocyclopenten-2-ones

We investigated the catalytic efficacy of silicotungstic acid (H4SiW12O40) polyoxometalate (POM) toward the reaction between furfural and amines that selectively yields trans-N,N-4,5-substituted-diaminocyclopenten-2-ones (trans-DACPs). H4SiW12O40 facilita