24241-74-5

Upstream product

• 107-13-1 acrylonitrile 
• 100-51-6 benzyl alcohol 
• 96-09-3 styrene oxide 
• 2517-76-2 3-iodopropanenitrile 
• 100-52-7 benzaldehyde 
• 75-05-8 acetonitrile 
• 100-42-5 styrene 
• 590-17-0 cyanomethyl bromide 
• 7555-67-1 1-phenylmethylenecyclopropane 
• 42436-86-2 2-phenylcyclobutanone 
• 624-75-9 iodoacetonitrile 
• 591-51-5 phenyllithium 
• 5343-98-6 4-oxo-4-phenylbutanenitrile 

Downstream Products

• 22050-10-8 (+/-)-5-phenyl-2-pyrrolidinone 
• 72335-16-1 4-chloro-4-phenylbutyronitrile 
• 111138-03-5 (R)-4-phenylbutyrolactone 
• 34674-93-6 4-hydroxy-4-phenylbutanoic acid 
• 1201-92-9 (S)-4-hydroxy-4-phenyl butyramide 
• 111138-02-4 (-)-(S)-5-phenyl-4,5-dihydrofuran-2(3H)-one 
• 154968-27-1 (R)-4-hydroxy-4-phenylbutanenitrile 

Relevant academic research and scientific papers

Expanding the Scope of Photocatalysis: Atom Transfer Radical Addition of Bromoacetonitrile to Aliphatic Olefins

An efficient photocatalyzed bromocyanomethylation of alkenes is reported. Among a range of organocatalysts and metal complexes, Ir(ppy)3 proved to be the best photocatalyst in promoting the addition of BrCH2CN to olefins. This photocatalytic atom transfer protocol can be expanded into a wide substrate scope of aliphatic olefins bearing various functional groups, leading to the corresponding products in good to excellent yields. In addition, linchpin catalysis was developed, since the bromo group can undergo further transformation into useful functional groups, such as the synthesis of amino acids.

Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles

A chemodivergent copper-catalyzed ring opening of cycloketone oximes via radical-mediated C-C bond cleavage under redox-neutral conditions is described. This method allows the divergent synthesis of γ- and δ-acyloxylated, alkoxylated, and hydroxylated nitriles while avoiding the use of toxic cyanide reagents. Moreover, these reactions proceed under very mild conditions with good functional group tolerance. Notably, ring-opening reactions of the less-strained substrate cyclopentanone oxime also proceeded well under the established conditions.

Radical-polar crossover reactions of vinylboron ate complexes

Vinyl boronic esters are valuable substrates for Suzuki-Miyaura cross-coupling reactions. However, boron-substituted alkenes have drawn little attention as radical acceptors, and the radical chemistry of vinylboron ate complexes is underexplored. We show here that carbon radicals add efficiently to vinylboron ate complexes and that their adduct radical anions undergo radical-polar crossover: A 1,2-alkyl/aryl shift from boron to the α-carbon sp2 center provides secondary or tertiary alkyl boronic esters. In contrast to the Suzuki-Miyaura coupling, a transition metal is not required, and two carbon-carbon bonds are formed. The valuable boronic ester moiety remains in the product and can be used in follow-up chemistry, enlarging the chemical space of the method. The cascade uses commercial starting materials and provides access to perfluoroalkylated alcohols, γ-lactones, γ-hydroxy alkylnitriles, and compounds bearing quaternary carbon centers.

Discovery of phenoxybutanoic acid derivatives as potent endothelin antagonists with antihypertensive activity

A series of phenoxybutanoic acid derivatives were synthesized and tested for their antagonistic activity on the contraction of the rat thoracic aortic ring induced by endothelin-1. Preliminary screening results showed that 6e and 6g with benzoheterocycles demonstrated significant antagonistic activities when compared to the reference compound BQ123. The results from additional assays for the binding affinity and selectivity for endothelin receptors showed that 6e was a selective ETA antagonist with a nanomolar IC50. Moreover, 6e was effective in relieving hypoxia-induced pulmonary arterial hypertension and right ventricular weight ratio. Therefore, 6e may have potential for further development as a therapeutic agent for the treatment of cardiovascular diseases.

Ene-carbonyl reductive coupling mediated by zinc and ammonia for the synthesis of γ-hydroxybutyric acid derivatives

The reductive coupling of an aryl carbonyl group with an activated alkene to give the corresponding γ-hydroxybutyric acid (GHBA) derivative was achieved in the presence of zinc and ammonia. A board scope of GHBA derivatives could be synthesized under ambient conditions by this method. A mechanism involving a Zn-ketyl radical as the key intermediate is proposed. Copyright

Zinc metal-promoted cross-coupling reaction of non-activated alkyl halides with aldehydes in the presence of chlorotrimethylsilane

Treatment of non-activated alkyl halides 1 with aldehydes 3 in the presence of zinc metal and chlorotrimethylsilane (TMSC1), DMA and/or NMP in THF brought about highly facile and effective cross-coupling to give the corresponding alcohols in good yield. These reactions are assumed to proceed through zinc reagent intermediates generated in situ.

Synthesis of Optically Active 4-Hydroxyalkanenitriles via an Enzymatic Reaction

Lipase-catalyzed enantioselective hydrolysis of esters of 4-hydroxyalkanenitriles was demonstrated for the first time.Efficient optical resolution was achieved when (+/-)-3-cyano-1-phenylpropyl 2-(phenylthio)acetate was hydrolyzed by lipase PS (Pseudomona

2-CYANOETHYLZINC IODIDE: A NEW REAGENT WITH REACTIVITY UMPOLUNG

2-Cyanoethylzinc iodide 1 generated in over 90percent yield from 3-iodopropionitrile and zinc in THF can be transmetallated to the copper and titanium derivatives 3 and 4 which react in good yields, respectively, with acyl chlorides, enones, allylic halides and benzaldehyde.

SYNTHESE VON γ-HYDROXYNITRILEN, γ-BUTYROLACTONEN UND α-METHYLENO-γ-BUTYROLACTONEN AUS EPOXIDEN UND NATRIUM-

The highly nucleophilic ylide-anion of sodium- attacks oxiranes by ring-opening.Depending on the work-up-conditions and the further reactions being employed, γ-hydroxynitriles, γ-butyrolactones or α-methyleno-γ-butyrolactones are obtained from the primary products thus formed.