2439-43-2

Usage

Uses

Used in Organic Synthesis:
2-Phenylbutyraldehyde is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a valuable building block for the creation of more complex molecules, which can be utilized in different fields such as pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Phenylbutyraldehyde is used as a starting material for the synthesis of various drugs and drug candidates. Its reactivity and structural features make it a suitable candidate for the development of new therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Flavor and Fragrance Industry:
2-Phenylbutyraldehyde is also used in the flavor and fragrance industry due to its unique aroma and flavor profile. It can be used to create a wide range of scents and flavors, adding depth and complexity to perfumes, colognes, and other fragrance products, as well as enhancing the taste and aroma of various food and beverage items.
Used in Chemical Research:
As a colorless oil with distinct chemical properties, 2-Phenylbutyraldehyde is also used in chemical research for studying various reaction mechanisms and exploring new synthetic pathways. Researchers can use 2-Phenylbutyraldehyde to gain insights into the behavior of similar molecules and develop new strategies for organic synthesis and compound design.

InChI:InChI=1/C10H12O/c1-2-9(8-11)10-6-4-3-5-7-10/h3-9H,2H2,1H3

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 108-86-1 bromobenzene 
• 3400-56-4 α-bromobutyraldehyde diethyl acetal 
• 2035-94-1 2-phenylbutan-1-ol 
• 53516-61-3 β-(n-Butyl-isobutylamino)-styrol 
• 75-03-6 ethyl iodide 
• 65439-59-0 3-(2-phenyl-butyryl)-thiazolidine-2-thione 
• 60860-46-0 trans-3-ethyl-3-phenyloxiranecarboxylic acid ethyl ester 
• 36854-57-6 2-Phenylbutyryl chloride 
• 1519-21-7 2-phenylbutyric anhydride 
• 75-24-1 trimethylaluminum 
• 78571-81-0 (3-benzyloxiran-2-yl)methanol 
• 75591-38-7 t-butyl β-ethyl-β-phenylglycidate 

Downstream Products

• 97234-84-9 3-phenyl-4-octanone 
• 4564-82-3 erythro-3-phenylpentan-2-ol 
• 4564-82-3 threo-3-phenylpentan-2-ol 
• 58343-21-8 3-phenylheptan-4-one 
• 138841-48-2 2-Methyl-4-phenyl-hexan-3-ol 
• 6006-69-5 4-phenylhexan-3-ol 
• 107847-29-0 (5RS,6RS)-5-hydroxy-2,2-dimethyl-6-phenyloctan-3-one 
• 107847-29-0 (5SR,6RS)-5-hydroxy-2,2-dimethyl-6-phenyloctan-3-one 
• 132278-77-4 (3,3-Dibromo-1-ethyl-allyl)-benzene 
• 106268-77-3 (4S,5S)-5-phenyl-1-hepten-4-ol 
• 106268-80-8 (4R,5R)-5-phenyl-1-hepten-4-ol 
• 106268-79-5 (4S,5R)-5-phenyl-1-hepten-4-ol 
• 106268-77-3 (4RS,5SR)-5-phenyl-1-hepten-4-ol 
• 106268-77-3 (4RS,5RS)-5-phenyl-1-hepten-4-ol 

Relevant academic research and scientific papers

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.

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.

A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.

Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds

A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines

The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).

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.

Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals

In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.

Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem-Diborylalkanes by an Asymmetric Allylic Substitution

We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X=Br, Cl) and their application in the synthesis of enantioenriched gem-diborylalkanes bearing a stereogenic center at the β-position of the diboryl groups by an asymmetric allylic substitution reaction. The reaction has a broad substrate scope, and various enantioenriched gem-diborylalkanes can be obtained in good yields with excellent enantioselectivity. Further elaboration of the enantioenriched gem-diborylalkanes provides access to a diverse set of valuable chiral building blocks.

Agent for reduction of sensory irritation

Provision of a TRPA1 activity inhibitor capable of reducing sensory irritation to skin or mucous membrane and an agent for reduction of sensory irritation for skin or mucous membrane. A TRPA1 inhibitor and an agent for reduction of sensory irritation for skin or mucous membrane comprising as an active ingredient a compound represented by the following formula (1) wherein R1 and R3 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R2 represents an alkyl group having 1 to 6 carbon atoms, R4 represents a hydrogen atom, a methyl group or an ethyl group, and a double line composed of a dotted line and a solid line represents a single bond or a double bond.