1002103-54-9

Upstream product

• 75-52-5 nitromethane 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 4192-77-2 ethyl cinnamate 
• 100-52-7 benzaldehyde 
• 102-96-5 (2-nitroethenyl)benzene 
• 75-07-0 acetaldehyde 
• 78-84-2 isobutyraldehyde 
• 15241-23-3 (Z)-nitrostyrene 
• 5153-67-3 nitrostyrene 

Downstream Products

• 15346-08-4 3-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-4H-chromen-4-one 
• 34687-03-1 4-nitro-3-phenylbutanoic acid methyl ester 
• 41441-41-2 4-nitro-3-phenyl butanoic acid 
• 1001860-22-5 (S)-4-nitro-3-phenylbutan-1-ol 
• 1001860-37-2 (R)-4-nitro-3-phenylbutan-1-ol 

Relevant academic research and scientific papers

Functionalization of Fe3O4 magnetic nanoparticles for organocatalytic Michael reactions

(S)-α,α-Diphenylprolinol trimethylsilyl ether supported onto well-defined (5.7 ± 1.1 nm) superparamagnetic Fe3O4 nanoparticles was used as a highly active, magnetically recoverable and reusable catalyst for the asymmetric, organocata

An Unexpected Promiscuous Activity of 4-Oxalocrotonate Tautomerase: The cis-trans Isomerisation of Nitrostyrene

Serendipitous switch: While exploring cis-nitrostyrene as a potential electrophile in Michael-type addition reactions catalysed by the enzyme 4-oxalocrotonate tautomerase (4-OT), it was unexpectedly found that 4-OT catalyses the isomerisation of cis-nitrostyrene to trans-nitrostyrene (kcat/Km= 1.9×103M-1s-1).

Unexpected reactivity of graphene oxide with DBU and DMF

An unusual reaction between GO, DBU and DMF, that typically uses base and solvent, has been thoroughly analyzed providing valuable basic knowledge about the reactivity of GO, which is essential to control functionalization and therefore the properties of

The role of streptavidin and its variants in catalysis by biotinylated secondary amines

Here, we combine the use of host screening, protein crystallography and QM/MM molecular dynamics simulations to investigate how the protein structure affects iminium catalysis by biotinylated secondary amines in a model 1,4 conjugate addition reaction. Monomeric streptavidin (M-Sav) lacks a quaternary structure and the solvent-exposed reaction site resulted in poor product conversion in the model reaction with low enantio- and regioselectivities. These parameters were much improved when the tetrameric host T-Sav was used; indeed, residues at the symmetrical subunit interface were proven to be critical for catalysis through a mutagenesis study. The use of QM/MM simulations and the asymmetric dimeric variant D-Sav revealed that both Lys121 residues which are located in the hosting and neighboring subunits play a critical role in controlling the stereoselectivity and reactivity. Lastly, the D-Sav template, though providing a lower conversion than that of the symmetric tetrameric counterpart, is likely a better starting point for future protein engineering because each surrounding residue within the asymmetric scaffold can be refined for secondary amine catalysis. This journal is

Asymmetric synthesis of piperidines using the nitro-Mannich reaction☆

A method for the synthesis of functionalized piperidines containing 3 contiguous stereocentres in the 2-,3- and 4- positions uses a diastereoselective nitro-Mannich to control stereochemistry. The nitro-Mannich reaction between a β-aryl/heteroaryl substituted nitroalkanes and glyoxylate imine provides β-nitro-amines with good selectivity (70:30 to >95:5) for the syn, anti-diastereoisomers. Reductive cyclisation with BF3.OEt2 and Et3SiH gave, after purification, stereochemically pure piperidines in 19–57% yield for ten examples with different 4-aryl/heteroaryl substituents.

Structure-activity relationships for binding of 4-substituted triazole-phenols to macrophage migration inhibitory factor (MIF)

Macrophage migration inhibitory factor (MIF) is a versatile protein that plays a role in inflammation, autoimmune diseases and cancers. Development of novel inhibitors will enable further exploration of MIF as a drug target. In this study, we investigated structure-activity relationships of MIF inhibitors using a MIF tautomerase activity assay to measure binding. Importantly, we notified that transition metals such as copper (II) and zinc (II) interfere with the MIF tautomerase activity under the assay conditions applied. EDTA was added to the assay buffer to avoid interference of residual heavy metals with tautomerase activity measurements. Using these assay conditions the structure-activity relationships for MIF binding of a series of triazole-phenols was explored. The most potent inhibitors in this series provided activities in the low micromolar range. Enzyme kinetic analysis indicates competitive binding that proved reversible. Binding to the enzyme was confirmed using a microscale thermophoresis (MST) assay. Molecular modelling was used to rationalize the observed structure-activity relationships. The most potent inhibitor 2d inhibited proliferation of A549 cells in a clonogenic assay. In addition, 2d attenuated MIF induced ERK phosphorylation in A549 cells. Altogether, this study provides insights in the structure-activity relationships for MIF binding of triazole-phenols and further validates this class of compounds as MIF binding agents in cell-based studies.

A class of polysubstituted benzene compounds and synergistic catalytic preparation method thereof

The invention relates to a class of polysubstituted benzene compounds and a synergistic catalytic preparation method thereof. The method comprises: generating a compound represented by a formula I defined in the specification from a compound defined in th

Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut

The two-step flow asymmetric synthesis of chiral γ-nitrobutyric acids as key intermediates of the GABA analogues baclofen, phenibut, and fluorophenibut is reported on a multigram scale. The telescoped process comprises an enantioselective Michael-type add

Asymmetric Michael reaction between aldehydes and nitroalkanes promoted by pyrrolidine-containing C2-symmetric organocatalysts

Bifunctional C2-symmetric organocatalysts derived from chiral 1,2-diaminoethanes and (S)-2-aminomethylpyrrolidine were fi rst used for promoting the asymmetric Michael addition of aliphatic aldehydes to nitroalkenes. The synthesized enantioenri

Reactivity and Selectivity of Iminium Organocatalysis Improved by a Protein Host

There has been growing interest in performing organocatalysis within a supramolecular system as a means of controlling reaction reactivity and stereoselectivity. Here, a protein is used as a host for iminium catalysis. A pyrrolidine moiety is covalently linked to biotin and introduced to the protein host streptavidin for organocatalytic activity. Whereas in traditional systems stereoselectivity is largely controlled by the substituents added to the organocatalyst, enantiomeric enrichment by the reported supramolecular system is completely controlled by the host. Also, the yield of the model reaction increases over 10-fold when streptavidin is included. A 1.1 ? crystal structure of the protein–catalyst complex and molecular simulations of a key intermediate reveal the chiral scaffold surrounding the organocatalytic reaction site. This work illustrates that proteins can be an excellent supramolecular host for driving stereoselective secondary amine organocatalysis.