2035-94-1

Usage

Uses

Used in Pharmaceutical Industry:
BETA-ETHYLPHENETHYL ALCOHOL 98 is used as a reagent for the synthesis of carbamate derivatives of Felbamate (F231000), which are potential anticonvulsant agents. This application is crucial for the development of new treatments for seizure disorders and epilepsy.
Additionally, BETA-ETHYLPHENETHYL ALCOHOL 98 is used to prepare analogs of O-(2-phenylethyl)-N-phenylthiocarbamate, which can serve as non-nucleoside HIV-1 reverse transcriptase inhibitors. This application is vital in the ongoing fight against HIV/AIDS, as it contributes to the development of new antiviral drugs that can help manage the disease and improve the quality of life for those affected.

InChI:InChI=1/C10H14O/c1-2-9(8-11)10-6-4-3-5-7-10/h3-7,9,11H,2,8H2,1H3/t9-/m1/s1

Upstream product

• 5453-68-9 1-(2-phenyl-butyryl)-piperidine 
• 99074-90-5 (2-ethyl-phenyl)-acetic acid amide 
• 2294-71-5 methyl 2-phenylbutanoate 
• 119-43-7 ethyl 2-phenylbutanoate 
• 2439-43-2 (2RS)-2-phenylbutanal 
• 96-09-3 styrene oxide 
• 2397-68-4 sodium tetraethylaluminate 
• 90-27-7 2-Phenylbutyric acid 
• 90-26-6 2-phenylbutyramide 
• 101-97-3 Ethyl 2-phenylethanoate 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 872045-33-5 (1-methoxybut-1-en-2-yl)benzene 
• 100-52-7 benzaldehyde 
• 444575-79-5 carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester 

Downstream Products

• 61257-27-0 4-nitro-benzoic acid-(2-phenyl-butyl ester) 
• 2439-43-2 (2RS)-2-phenylbutanal 
• 33442-47-6 (S)-2-phenylbutan-1-ol 
• 16460-75-6 (R)-2-phenyl-butan-1-ol 
• 172585-58-9 (S)-2-phenylbutyl acetate 
• 128126-09-0 (3,5-Dinitro-phenyl)-carbamic acid (R)-2-phenyl-butyl ester 
• 137037-10-6 (3,5-Dinitro-phenyl)-carbamic acid (S)-2-phenyl-butyl ester 
• 109114-13-8 (+/-)-2-phenylbutyl acetate 
• 93-55-0 1-phenyl-propan-1-one 
• 824-90-8 1-phenylbut-1-ene 
• 2039-93-2 1-ethylstyrene 
• 66050-89-3 (2R)-2-phenylbutyl (R)-α-methoxy-α-trifluoromethylphenylacetate 
• 66050-90-6 (2S)-2-phenylbutyl (R)-α-methoxy-α-trifluoromethylphenylacetate 
• 1171948-15-4 O-(2-phenyl-butyl)-O'-phenyl carbonate 

Relevant academic research and scientific papers

Highly efficient NHC-iridium-catalyzed β-methylation of alcohols with methanol at low catalyst loadings

The methylation of alcohols is of great importance since a broad number of bioactive and pharmaceutical alcohols contain methyl groups. Here, a highly efficient β-methylation of primary and secondary alcohols with methanol has been achieved by using bis-N-heterocyclic carbene iridium (bis-NHC-Ir) complexes. Broad substrate scope and up to quantitative yields were achieved at low catalyst loadings with only hydrogen and water as by-products. The protocol was readily extended to the β-alkylation of alcohols with several primary alcohols. Control experiments, along with DFT calculations and crystallographic studies, revealed that the ligand effect is critical to their excellent catalytic performance, shedding light on more challenging Guerbet reactions with simple alcohols. [Figure not available: see fulltext.].

Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides

We present a highly efficient convergent asymmetric hydrogenation of E/Z mixtures of enamides catalyzed by N,P-iridium complexes supported by mechanistic studies. It was found that reduction of the olefinic isomers (E and Z geometries) produces chiral amides with the same absolute configuration (enantioconvergent hydrogenation). This allowed the hydrogenation of a wide range of E/Z mixtures of trisubstituted enamides with excellent enantioselectivity (up to 99% ee). A detailed mechanistic study using deuterium labeling and kinetic experiments revealed two different pathways for the observed enantioconvergence. For α-aryl enamides, fast isomerization of the double bond takes place, and the overall process results in kinetic resolution of the two isomers. For α-alkyl enamides, no double bond isomerization is detected, and competition experiments suggested that substrate chelation is responsible for the enantioconvergent stereochemical outcome. DFT calculations were performed to predict the correct absolute configuration of the products and strengthen the proposed mechanism of the iridium-catalyzed isomerization pathway.

syn-Selective Michael Reaction of α-Branched Aryl Acetaldehydes with Nitroolefins Promoted by Squaric Amino Acid Derived Bifunctional Br?nsted Bases

Here we describe a direct access to 2,2,3-trisubstituted syn γ-nitroaldehydes by addition of α-branched aryl acetaldehydes to nitroolefins promoted by a cinchona based squaric acid-derived amino acid peptide. Different α-methyl arylacetaldehydes react with β-aromatic and β-alkyl nitroolefins to afford the Michael adducts in high enantioselectivity and syn-selectivity. NMR experiments and DFT calculations predict the reaction to occur through the intermediacy of E-enolate. The interaction between the substrates and the catalyst follows Pápai's model, wherein an intramolecular H-bond interaction in the catalyst between the NH group of one of the tert-leucines and the squaramide oxygen seems to be key for discrimination of the corresponding reaction transition states.

Copper-catalyzed hydroformylation and hydroxymethylation of styrenes

Hydroformylation catalyzed by transition metals is one of the most important homogeneously catalyzed reactions in industrial organic chemistry. Millions of tons of aldehydes and related chemicals are produced by this transformation annually. However, most of the applied procedures use rhodium catalysts. In the procedure described here, a copper-catalyzed hydroformylation of alkenes has been realized. Remarkably, by using a different copper precursor, the aldehydes obtained can be further hydrogenated to give the corresponding alcohols under the same conditions, formally named as hydroxymethylation of alkenes. Under pressure of syngas, various aldehydes and alcohols can be produced from alkenes with copper as the only catalyst, in excellent regioselectivity. Additionally, an all-carbon quaternary center containing ethers and formates can be synthesized as well with the addition of unactivated alkyl halides. A possible reaction pathway is proposed based on our results. This journal is

Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction

The development of a C2-extension of primary alcohols with ethanol as the C2 source and catalysis by [Cp*IrCl2]2 (where Cp? = pentamethylcyclopentadiene) is described. This new extension system was used for a range of benzylic alcohol substrates and for aliphatic alcohols with ethanol as an alkyl reagent to generate the corresponding C2-extended linear alcohols. Mechanistic studies of the reaction by means of intermediates and deuterium labeling experiments suggest the reaction is based on hydrogen autotransfer.

Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation

A magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product formation.

Manganese-catalysed transfer hydrogenation of esters

Manganese catalysed ester reduction using ethanol as a hydrogen transfer agent in place of dihydrogen is reported. High yields can be achieved for a range of substrates using 1 mol% of a Mn(i) catalyst, with an alkoxide promoter. The catalyst is derived from a tridentate P,N,N ligand.

Highly Enantioselective Catalytic Kinetic Resolution of α-Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides

A new catalytic methodology was developed to promote an efficient one-pot kinetic resolution of racemic aldehydes with selectivity (s*) of up to 91 (99:1 d.r., >99 % ee) in a cycloaddition reaction with enolizable anhydrides to afford dihydroisocoumarin products (a core prevalent in natural products and molecules of medicinal interest) containing three contiguous stereocentres.

A is by aromatic carboxylic acid non-catalytic reaction of alcohol compound (by machine translation)

The present invention discloses a non-catalytic reaction of the aromatic carboxylic acid preparation of alcohol compound. In an inert gas atmosphere, after dehydration and deoxidation treatment of the reaction bottle [...] borane and carboxylic acid stirring and mixing, reaction 6 - 12 hours to obtain borate, further hydrolyzed into alcohol; said carboxylic acid is benzoic acid, 4 - bromobenzoic acid, 4 - fluoro benzoic acid, 1 - naphthoic acid, 2 - methoxybenzene formic acid and the like. The invention for the first time in the absence of catalyst under the conditions of high-efficiently using carboxylic acid with borane generating borohydrite reaction, carbonyl compound with borane generating borohydrite reaction preparation borate, further hydrolysis alcohol, provides new programme. (by machine translation)

Method for preparing alcoholic compound from anilino lithium compound as catalyst

The invention relates to an application of an anilino lithium compound, in particular to a method for preparing an alcoholic compound from the anilino lithium compound as a catalyst. The catalyst, borane and carboxylic acid are stirred and mixed uniformly, subjected to a reaction and exposed to air to terminate the reaction, a reacted liquid is subjected to reduced-pressure treatment for solvent removal, silica gel and methanol are added, and the alcoholic compound is obtained by hydrolysis. The anilino lithium compound can perform high-activity catalysis on the reaction between carboxylic acid and borane at room temperature, dose of the catalyst is only 0.8mol% of the mole ratio of carboxylic acid, compared with the conventional catalysis system, the commercial reagent anilino lithium compound is used, reaction conditions are mild, and yield of borate with different substituents under limit conditions can reach 90% or higher.