5406-12-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-METHYLPHENYL)PROPIONALDEHYDE is used as a reagent for the treatment and prevention of rabies and cancer. It plays a crucial role in the development of vaccines and therapeutic agents targeting these diseases. Its chemical properties allow it to interact with specific biological targets, making it a valuable component in the formulation of medicines.
In the context of rabies, 3-(4-METHYLPHENYL)PROPIONALDEHYDE is used as a key component in the synthesis of vaccines that stimulate the immune system to produce antibodies against the rabies virus. This helps in preventing the onset of the disease and provides protection to individuals who have been exposed to the virus.
In the fight against cancer, 3-(4-METHYLPHENYL)PROPIONALDEHYDE is utilized in the development of therapeutic agents that target cancer cells. It may be involved in the synthesis of drugs that can inhibit the growth and proliferation of cancer cells, thereby contributing to the treatment of various types of cancer.

InChI:InChI=1/C10H12O/c1-9-4-6-10(7-5-9)3-2-8-11/h4-8H,2-3H2,1H3

Upstream product

• 108-88-3 toluene 
• 107-02-8 acrolein 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 201230-82-2 carbon monoxide 
• 122-51-0 orthoformic acid triethyl ester 
• 50-00-0 formaldehyd 
• 123-63-7 paracetaldehyde 
• 20461-86-3 2,2-diethoxy acetic acid 
• 64-18-6 formic acid 
• 56578-35-9 4-methyl-cinnamaldehyde 
• 624-31-7 4-tolyl iodide 
• 107-18-6 allyl alcohol 
• 1866-39-3 trans-p-methylcinnamic acid 
• 56955-36-3 methyl 3-(p-tolyl)propionate 

Downstream Products

• 75676-87-8 6-(p-tolyl)-trans-3-hexen-2-one 
• 1180845-22-0 C₁₆H₁₉NO₂ 
• 1370589-96-0 (E)-ethyl-5-(p-tolyl)pent-2-enoate 
• 1357295-67-0 1-(2-bromobenzyl)-5-(4-methylbenzyl)-3,4-dihydropyridin-2(1H)-one 
• 1357295-70-5 1-(2-bromo-5-methoxybenzyl)-5-(4-methylbenzyl)-3,4-dihydropyridin-2(1H)-one 
• 1357295-71-6 1-(2-bromo-4,5-dimethoxybenzyl)-5-(4-methylbenzyl)-3,4-dihydropyridin-2(1H)-one 
• 1357295-77-2 1-(4-methylbenzyl)-2,6-dihydropyrido[2,1-a]isoindol-4(3H)-one 
• 1357295-81-8 8-methoxy-1-(4-methylbenzyl)-2,6-dihydropyrido[2,1-a]isoindol-4(3H)-one 
• 1357295-82-9 8,9-dimethoxy-1-(4-methylbenzyl)-2,6-dihydropyrido[2,1-a]isoindol-4(3H)-one 
• 1357295-64-7 ethyl 4-formyl-5-(4-methylphenyl)pentanoate 
• 1126906-47-5 (R)-2-(3-oxo-1-(4-methylphenyl)propyl)malonic acid diethyl ester 
• 1449418-64-7 (R)-2-ethoxycarbonyl-3-(4-methylphenyl)pentane-1,5-dioic acid 1,5-diethyl ester 
• 56578-35-9 4-methyl-cinnamaldehyde 

Relevant academic research and scientific papers

Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis

Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).

Synthesis of rac-ɑ-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst

This work detailed the preparation of a class of water-soluble PNP ligands that differed by the nature of the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic transformation demonstrated synthetic application of this methodology for non-steroidal antiinflammatory drugs.

Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalysts

Here, the streptavidin-biotin technology was applied to enable organocatalytic transfer hydrogenation. By introducing a biotin-tethered pyrrolidine (1) to the tetrameric streptavidin (T-Sav), the resulting hybrid catalyst was able to mediate hydride transfer from dihydro-benzylnicotinamide (BNAH) to α,β-unsaturated aldehydes. Hydrogenation of cinnamaldehyde and some of its aryl-substituted analogues was found to be nearly quantitative. Kinetic measurements revealed that the T-Sav:1 assembly possesses enzyme-like behavior, whereas isotope effect analysis, performed by QM/MM simulations, illustrated that the step of hydride transfer is at least partially rate-limiting. These results have proven the concept thatT-Savcan be used to host secondary amine-catalyzed transfer hydrogenations.

Insight into decomposition of formic acid to syngas required for Rh-catalyzed hydroformylation of olefins

Formic acid (FA) is one kind of important bulk chemicals, which is recognized as a sustainable and eco-friendly energy carrier to transport H2 via dehydrogenation or CO via decarbonylation. Expectantly, FA upon decomposition into H2 and CO could be used as the syngas alternative for hydroformylation. In this paper, the behaviors of FA to release H2 as well as CO following the distinct pathways were carefully investigated for the first time, and then established a new hydroformylation protocol free of syngas. It was found that the atmospheric hydroformylation of olefins with formic acid (FA) as syngas alternative was smoothly fulfilled over Xantphos (L1) modified Rh-catalyst under mild conditions (80 °C, Rh concentration 1 mol %, 14 h), resulting in >90% conversion of the olefins along with the high selectivity to the target aldehydes (>93%). By using FA as syngas source, the side-reaction of olefin-hydrogenation was greatly depressed. The in situ FT-IR and the high-pressure 1H NMR spectroscopic analyses were applied to reveal how FA behaves dually as CO surrogate and hydrogen source over L1-Rh(acac)(CO)2 catalytic system, based on which the deeply insight into the catalytic mechanism of hydroformylation of olefins with FA as syngas alternative was offered.

CoPd Nanoalloys with Metal–Organic Framework as Template for Both N-Doped Carbon and Cobalt Precursor: Efficient and Robust Catalysts for Hydrogenation Reactions

In this work, a series of metal–organic framework (MOF)-derived CoPd nanoalloys have been prepared. The nanocatalysts exhibited excellent activities in the hydrogenation of nitroarenes and alkenes in green solvent (ethanol/water) under mild conditions (H2 balloon, room temperature). Using ZIF-67 as template for both carbon matrix and cobalt precursor coating with a mesoporous SiO2 layer, the catalyst CoPd/NC@SiO2 was smoothly constructed. Catalytic results revealed a synergistic effect between Co and Pd components in the hydrogenation process due to the enhanced electron density. The mesoporous SiO2 shell effectively prevented the sintering of hollow carbon and metal NPs at high temperature, furnishing the well-dispersed nanoalloy catalysts and better catalytic performance. Moreover, the catalyst was durable and showed negligible activity decay in recycling and scale-up experiments, providing a mild and highly efficient way to access amines and arenes.

Diaza-Crown Ether-Bridged Chiral Diphosphoramidite Ligands: Synthesis and Applications in Asymmetric Catalysis

A small library of diaza-crown ether-bridged chiral diphosphoramidite ligands was prepared. In the rhodium-catalyzed asymmetric hydrogenation and hydroformylation reactions, these ligands exhibited distinct properties in catalytic activity and/or enantioselectivity. Hydrogenated products with opposite absolute configurations could be obtained in high yields with excellent ee values by utilizing (S,S)-L1 and (S,S)-L3, respectively. Meanwhile, the addition of alkali metal cations caused variations in catalytic outcomes, showing the supramolecular tunability of these Rh/diphosphoramidite catalytic systems.

Styrene Hydroformylation with In Situ Hydrogen: Regioselectivity Control by Coupling with the Low-Temperature Water–Gas Shift Reaction

The hydroformylation of olefins is one of the most important homogeneously catalyzed industrial reactions for aldehyde synthesis. Various ligands can be used to obtain the desired linear aldehydes in the hydroformylation of aliphatic olefins. However, in the hydroformylation of aromatic substrates, branched aldehydes are formed preferentially with common ligands. In this study, a novel approach to selectively obtain linear aldehydes in the hydroformylation of styrene and its derivatives was developed by coupling with a water–gas shift reaction on a Rh single-atom catalyst without the use of ligands. Detailed studies revealed that the hydrogen generated in situ from the water–gas shift is critical for the highly regioselective formation of linear products. The coupling of a traditional homogeneous catalytic process with a heterogeneous catalytic reaction to tune product selectivity may provide a new avenue for the heterogenization of homogenous catalytic processes.

Rhodium-Catalyzed Remote C(sp3)?H Borylation of Silyl Enol Ethers

A rhodium-catalyzed remote C(sp3)?H borylation of silyl enol ethers (SEEs, E/Z mixtures) by alkene isomerization and hydroboration is reported. The reaction exhibits mild reaction conditions and excellent functional-group tolerance. This method is compatible with an array of SEEs, including linear and branched SEEs derived from aldehydes and ketones, and provides direct access to a broad range of structurally diverse 1,n-borylethers in excellent regioselectivities and good yields. These compounds are precursors to various valuable chemicals, such as 1,n-diols and aminoalcohols.

Carbene-Catalyzed α-Carbon Amination of Chloroaldehydes for Enantioselective Access to Dihydroquinoxaline Derivatives

An NHC-catalyzed α-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.

Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ-Diolcarbonate Aldehydes to (E)-γ-Hydroxy-α,β-enals

A tandem IBX-promoted oxidation of primary alcohol to aldehyde and opening of intermediate β,γ-diolcarbonate aldehyde to (E)-γ-hydroxy-α,β-enal has been developed. Remarkably, the carbonate opening delivered exclusively (E)-olefin and no over-oxidation of γ-hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both (S)- and (R)-coriolides and d-xylo- and d-arabino-C-20 guggultetrols.