20259-49-8

Upstream product

• 5153-67-3 nitrostyrene 
• 102-96-5 (2-nitroethenyl)benzene 
• 6125-24-2 2-Phenylnitroethane 
• 122-78-1 phenylacetaldehyde 
• 100-52-7 benzaldehyde 

Downstream Products

• 140-29-4 phenylacetonitrile 
• 60-12-8 2-phenylethanol 
• 20268-21-7 (E)-2-phenylacetaldehyde oxime 

Relevant academic research and scientific papers

Chemo-promiscuity of alcohol dehydrogenases: reduction of phenylacetaldoxime to the alcohol

The reduction of phenylacetaldoxime was catalysed by alcohol dehydrogenases in the presence of NAD(P)H yielding finally the primary alcohol via the imine and aldehyde intermediates. This suggests that the hydride of the cofactor NAD(P)H is transferred to the N-atom of the oxime moiety and not to the carbon atom, as usual stated. This reaction represents the first example of a catalytic chemo-promiscuity of alcohol dehydrogenases.

Increasing Temperature Changes Flux into Multiple Biosynthetic Pathways for 2-Phenylethanol in Model Systems of Tea (Camellia sinensis) and Other Plants

2-Phenylethanol (2PE) is a representative aromatic aroma compound in tea (Camellia sinensis) leaves. However, its formation in tea remains unexplored. In our study, feeding experiments of [2H8]L-phenylalanine (Phe), [2Hsu

Improved Synthesis of Glucosinolates

Herein we describe an improved synthesis of glucosinolates, in which the quantity and cost of materials have been reduced by approximately an order of magnitude compared to typical literature procedures. This allowed us to produce multiple glucosinolates in 10-25 gram batches using vessel sizes no larger than 0.5 litres.

New insights into the catalytic reduction of aliphatic nitro compounds with hypophosphites under ultrasonic irradiation

This work describes an efficient process for the reduction of nitro compounds to the corresponding amines with a catalytic amount of Pd/C (0.6 mol%), and a mixture of sodium hypophosphite and hypophosphorous acid as a reducing agent in H2O/2-MeTHF at 60 °C. The reaction was optimized under silent conditions. The conditions for the in situ production of H2 using the mixture NaH2PO2/H3PO2 were studied. The influence of ultrasonic activation was investigated both in terms of efficiency and kinetics. The reaction was shown to be efficient in water, at 70 °C with a quantitative conversion and a maximal yield in only 15 min thanks to the ultrasonic activation. Finally, ultrasound was proved to act as a physical agent of phase transfer.

Cyanide-Free and Broadly Applicable Enantioselective Synthetic Platform for Chiral Nitriles through a Biocatalytic Approach

A cyanide-free platform technology for the synthesis of chiral nitriles by biocatalytic enantioselective dehydration of a wide range of aldoximes is reported. The nitriles were obtained with high enantiomeric excess of >90 % ee (and up to 99 % ee) in many cases, and a “privileged substrate structure” with respect to high enantioselectivity was identified. Furthermore, a surprising phenomenon was observed for the enantiospecificity that is usually not observed in enzyme catalysis. Depending on whether the E or Z isomer of the racemic aldoxime substrate was employed, one or the other enantiomer of the corresponding nitrile was formed preferentially with the same enzyme.

New approach to oximes through reduction of nitro compounds enabled by visible light photoredox catalysis

A range of nitro compounds are smoothly reduced to their corresponding oximes under the synergistic effects of visible light irradiation, the Ru(bpy)3Cl2 photocatalyst, Hünig's base, Mg(ClO 4)2 activation, and MeCN solvent. This remarkably mild and environmentally benign protocol, when orchestrated with classical Beckmann rearrangement, enables such high-value industrial feedstock as caprolactam to be readily accessed from simple precursor nitrocyclohexane.

Design, synthesis, and structure-activity relationships of 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazoles as TGR5 agonists

Given its role in the mediation of energy and glucose homeostasis, the G-protein-coupled bile acid receptor1 (TGR5) is considered a potential target for the treatment of type2 diabetes mellitus and other metabolic disorders. By thorough analysis of diverse structures of published TGR5 agonists, a hypothetical ligand-based pharmacophore model was built, and a new class of potent TGR5 agonists, based on the novel 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazole core, was discovered by rational design. Three distinct synthetic methods for constructing 4,5-dihydro-1,2,4-oxadiazoles and extensive structure-activity relationship studies are reported herein. Compound (R)-54n, the structure of which was determined by single-crystal X-ray diffraction and quantum chemical solid-state TDDFT-ECD calculations, showed the best potency, with an EC50 value of 1.4nM toward hTGR5. Its favorable properties invitro warrant further investigation.

Synthesis of highly substituted pyrroles via nucleophilic catalysis

Figure presented. A nucleophilic catalysis method providing a concise synthesis of di-, tri-, and tetrasubstituted pyrroles is described. This regioselective one-pot method relies on nucleophilic catalysis of the intermolecular addition of oximes to activ

Solventless rapid synthesis of oxime, semicarbazone, and phenylhydrazone derivatives from carbonyl compounds under microwave conditions

A rapid and efficient method for the synthesis of oximes, semicarbazones, and phenylhydrazones has been reported under solventless conditions using microwave irradiation. CSIRO 2005.

Emission of 2-phenylethanol from its β-D-glucopyranoside and the biogenesis of these compounds from [2H8] L-phenylalanine in rose flowers

The hydrolysis of 2-phenylethyl β-D-glucopyranoside (3) was found to be partially inhibited by feeding with 2-phenyl-N-glucosyl-acetamidiumbromide (8), a β-glucosidase inhibitor, resulting in a decrease in the diurnal emission of 2-phenylethanol (2) from