119718-89-7

Usage

Uses

Used in Chemical Synthesis:
(R)-ALPHA-CYANOBENZYL ACETATE is used as a model compound for [chemical synthesis] for [its unique structure and reactivity]. It is particularly useful in the synthesis of secondary amides through an aryl?N-addition reaction to the -CN group of nitriles. This process can be promoted by iodine or t-BuONO, which facilitates the formation of the desired products.
Used in Pharmaceutical Research:
(R)-ALPHA-CYANOBENZYL ACETATE is used as a key intermediate in the development of new pharmaceutical compounds for [various therapeutic applications]. Its unique structure and reactivity make it a valuable building block for the synthesis of novel drug candidates, potentially leading to the discovery of new treatments for various diseases and conditions.
Used in Research and Development:
(R)-ALPHA-CYANOBENZYL ACETATE is used as a research tool in [academic and industrial laboratories] for [exploring new reaction pathways and understanding the fundamental chemistry of nitriles and amides]. Its use in research can lead to the development of new synthetic methods, improved reaction conditions, and a deeper understanding of the underlying chemical processes.

InChI:InChI=1/C10H9NO2/c1-8(12)13-10(7-11)9-5-3-2-4-6-9/h2-6,10H,1H3/t10-/m0/s1

Upstream product

• 532-28-5 (RS)-mandelonitrile 
• 108-24-7 acetic anhydride 
• 18942-90-0 2-nitro-1-phenylethyl acetate 
• 613-90-1 benzoyl cyanide 
• 151-50-8 potassium cyanide 
• 100-52-7 benzaldehyde 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 140-29-4 phenylacetonitrile 
• 631-57-2 Acetyl cyanide 
• 2408-36-8 lithium cyanide 
• 75-36-5 acetyl chloride 
• 7677-24-9 trimethylsilyl cyanide 
• 581-55-5 benzylidene 1,1-diacetate 
• 143-33-9 sodium cyanide 

Downstream Products

• 40060-76-2 (±)-phenyl(1H-tetrazol-5-yl)methanol 
• 4442-85-7 2-cyclohexylethylamine 
• 64-04-0 phenethylamine 
• 22094-21-9 2-acetoxy-2-phenylacetaldehyde 
• 10020-96-9 (R)-Mandelonitrile 
• 28549-12-4 (S)-mandelonitrile 
• 119718-88-6 O-acetyl (S)-mandelonitrile 
• 1823-91-2 1-phenylethyl cyanide 
• 7568-93-6 2-Amino-1-phenylethanol 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 279685-83-5 (2R)-phenyl[(tetrahydropyran-2-yloxy)]acetonitrile 
• 129313-24-2 O-butyryl-(S)-2-hydroxy-2-phenylacetonitrile 
• 120390-75-2 (R)-(+)-α-<(tert-butyldimethylsilyl)oxy>-benzeneacetonitrile 
• 147329-37-1 (S)-(-)-α-<(tert-butyldimethylsilyl)oxy>benzeneacetonitrile 

Relevant academic research and scientific papers

Combination of the Lipase-Catalysed Resolution with Mitsunobu Esterification in One Pot

A chemo-enzymatic method for the preparation of homochiral esters of 14 secondary alcohols with 100percent theoretical yields is described in one pot through two steps: the lipase-catalysed kinetic resolution followed by the Mitsunobu esterification of the free alcohol enantiomer in situ in the resolution mixture.Mathematical equations which link the enzymatic and chemical steps were derived, resulting in an enantioconvergent synthetic tool for the preparation of chiral intermediates.

Asymmetric Cyanosilylation of Aldehydes by a Lewis Acid/Base Synergistic Catalyst of Chiral Metal Clusters

Metal clusters with well-defined crystal structures are extremely useful for studying the synergistic catalytic effects and associated catalytic mechanisms. In this study, two pairs of chiral lanthanide-transition metal clusters (R)/(S)-Co3Ln2(Ln = Tb or Dy) were synthesized using Schiff-base ligands [(R)- or (S)-H3L] with multiple Lewis base sites (O sites). The as-prepared (R)/(S)-Co3Ln2chiral metal clusters exhibited good catalytic functionality in the asymmetric synthesis of chiral cyanohydrins, with high conversions of up to 99% and medium-to-high enantiomeric excess values of up to 78%. The catalysis process followed a mechanism in which the bifunctional metal clusters of (R)/(S)-Co3Ln2, containing Lewis acid sites and Lewis base sites, simultaneously activated the aldehydes and trimethylsilyl cyanide, respectively. Consequently, synergistic catalysis was realized. The enantioselectivity of the different aldehydes and stereochemical configuration of the resulting products are attributed to the formation of a steric chiral pocket via the external chiral ligands on the clusters. In addition, heterogeneous asymmetric cyanosilylation using (R)/(S)-Co3Ln2chiral metal clusters achieved high chemoselectivity and regioselectivity under mild conditions.

A High-Throughput Screening Method for the Directed Evolution of Hydroxynitrile Lyase towards Cyanohydrin Synthesis

Chiral cyanohydrins are useful intermediates in the pharmaceutical and agricultural industries. In nature, hydroxynitrile lyases (HNLs) are a kind of elegant tool for enantioselective hydrocyanation of carbonyl compounds. However, currently available methods for demonstrating hydrocyanation are still stalled at precise, but low-throughput, GC or HPLC analyses. Herein, we report a chromogenic high-throughput screening (HTS) method that is feasible for the cyanohydrin synthesis reaction. This method was highly anti-interference and sensitive, and could be used to directly profile the substrate scope of HNLs either in cell-free extract or fermentation clear broth. This HTS method was also validated by generating new variants of PcHNL5 that presented higher catalytic efficiency and stronger acidic tolerance in variant libraries.

Constructing a triangular metallacycle with salen-Al and its application to a catalytic cyanosilylation reaction

A triangular metallosalen-based metallacycle was constructed in quantitative yield by the self-assembly of a 180° bis(pyridyl)salen-Al complex and a 60° diplatinum(ii) acceptor in a 1?:?1 stoichiometric ratio. This metallacycle was then successfully used to cyanosilylate a wide range of benzaldehydes with trimethylsilyl cyanide.

Palladium-catalyzed C-H activation of simple arenes and cascade reaction with nitriles: access to 2,4,5-trisubstituted oxazoles

An efficient and straightforward protocol for the assembly of the pharmaceutically and biologically valuable oxazole skeleton is achieved for the first time from readily available simple arenes and functionalized aliphatic nitriles. This transformation in

Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles

We herein report an efficient approach for the assembly of multiply substituted imidazoles and oxazoles in a single-step manner. These transformations are based on a decarboxylation addition and annulation of readily accessible aromatic carboxylic acids a

Divergent Palladium-Catalyzed Tandem Reaction of Cyanomethyl Benzoates with Arylboronic Acids: Synthesis of Oxazoles and Isocoumarins

A palladium-catalyzed tandem reaction of cyanomethyl benzoates with arylboronic acids has been achieved. Substitution at the 2-position of cyanomethyl benzoates was found to be crucial for the selective synthesis of oxazoles and isocoumarins. Cyanomethyl

Preparation method and application of a chiral Zr-MOF catalyst

The invention relates to a preparation method and application of a chiral Zr-MOF catalyst and belongs to the technical field of chiral catalyst preparation. The structural formula of an organic ligandL of the chiral Zr-MOF catalyst is (R)-4,4'-dimethoxyca

Homochiral BINAPDA-Zr-MOF for Heterogeneous Asymmetric Cyanosilylation of Aldehydes

A new homochiral BINAPDA-Zr-MOF was prepared by a new chiral organic linker of (R)-4,4′-(6,6′-dichloro-2,2′-diethoxyl-[1,1′-binaphthalene]-4,4′-diyl)dibenzoic acid (R-L) and ZrCl4 under solvothermal conditions. Its structure was determined by P

Supported Ionic Liquid-Like Phases (SILLPs) as Immobilised Catalysts for the Multistep and Multicatalytic Continuous Flow Synthesis of Chiral Cyanohydrins

Supported Ionic Liquid-Like Phases have been found to be efficient organocatalysts for the synthesis of cyanohydrin esters under solvent-free conditions by an “electrophile-nucleophile dual activation” based on hydrogen bond formation. The combination of