20401-88-1

Usage

Uses

Used in Chemical Synthesis:
3-(4-METHOXY-PHENYL)-PROPIONALDEHYDE is used as a reactant/reagent for facilitating various organic reactions and syntheses. Its chemical properties make it a versatile compound in the creation of different organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(4-METHOXY-PHENYL)-PROPIONALDEHYDE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its reactivity and structural features contribute to the development of new drugs and medications.
Used in Flavor and Fragrance Industry:
3-(4-METHOXY-PHENYL)-PROPIONALDEHYDE is also utilized as a component in the flavor and fragrance industry. Its unique chemical structure allows it to contribute distinct and desirable scents to various products.
Used in Research and Development:
In the field of research and development, 3-(4-METHOXY-PHENYL)-PROPIONALDEHYDE serves as a key compound for studying organic chemistry and exploring new synthetic pathways. Its properties and reactivity make it an essential tool for scientists and researchers in their quest for new discoveries and innovations.

Synthesis Reference(s)

Synthesis, p. 526, 1976 DOI: 10.1055/s-1976-24106

InChI:InChI=1/C10H12O2/c1-12-10-6-4-9(5-7-10)3-2-8-11/h4-8H,2-3H2,1H3

Upstream product

• 15893-42-2 3-(4-methoxyphenyl)propionyl chloride 
• 637-69-4 4-Methoxystyrene 
• 201230-82-2 carbon monoxide 
• 115755-20-9 2-[2-(4-Methoxy-phenyl)-ethyl]-3-methyl-thiazolidine 
• 122901-00-2 1-Methoxy-3-(4-methoxyphenyl)-1-(4-nitrophenixy)propane 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 100-66-3 methoxybenzene 
• 107-02-8 acrolein 
• 15795-54-7 5-(4-methoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 15823-04-8 methyl 3-(4-methoxyphenyl)propionate 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 634-36-6 1,2,3-trimethoxybenzene 
• 61958-46-1 5-(4-methoxybenzyl)-2,2-dimethyl[1,3]dioxane-4,6-dione 

Downstream Products

• 91337-83-6 3-(4-methoxy-phenyl)-propionaldehyde-semicarbazone 
• 82267-46-7 DL-2-amino-4-(p-methoxyphenyl)butanoic acid 
• 74185-15-2 1,7-bis(4-methoxyphenyl)heptan-3-ol 
• 122948-44-1 3-(p-methoxyphenyl)propanal dimethylacetal 
• 210173-44-7 N-[3-(4-methoxy-phenyl)-propylidene]-N'-pyridin-4-yl-hydrazine 
• 477773-68-5 ethyl (E)-5-(4-methoxyphenyl)pent-2-enoate 
• 177616-01-2 5-(4'-methoxyphenyl)-2(E)-pentenoic acid 
• 375856-74-9 (R)-3-(4-methoxyphenyl)propane-1,2-diol 
• 922167-77-9 acetic acid 2-acetoxymethyl-6-hydroxy-8-(4-methoxy-phenyl)-oct-3-enyl ester 
• 922167-79-1 2-{4-hydroxy-2-(4-methoxy-phenyl)-6-[2-(4-methoxy-phenyl)-ethyl]-tetrahydro-pyran-3-yl}-propane-1,3-diol 
• 922167-78-0 acetic acid 3-(2-acetoxy-1-acetoxymethyl-ethyl)-2-(4-methoxy-phenyl)-6-[2-(4-methoxy-phenyl)-ethyl]-tetrahydro-pyran-4-yl ester 
• 922167-80-4 thiocarbonic acid O-(3-hydroxy-2-{4-hydroxy-2-(4-methoxy-phenyl)-6-[2-(4-methoxy-phenyl)-ethyl]-tetrahydro-pyran-3-yl}-propyl) ester O-phenyl ester 
• 922167-89-3 5-(4-methoxy-phenyl)-2,7-bis-[2-(4-methoxy-phenyl)-ethyl]-hexahydro-pyrano[4,3-b]pyran-4-carbaldehyde 
• 922167-87-1 5-(4-methoxy-phenyl)-2,7-bis-[2-(4-methoxy-phenyl)-ethyl]-hexahydro-pyrano[4,3-b]pyran-4-carbaldehyde 

Relevant academic research and scientific papers

Conjugate addition of electron-rich aromatics to acrolein in the confined space of zeolite Y

Acrolein gas was spontaneously entrapped in supercages of NaY zeolite and the sorption was confirmed by solid 13C MAS NMR spectra. In the confined cavities, acrolein smoothly underwent conjugate addition with electron-rich aromatics such as ind

Asymmetric Multifunctional Modular Organocatalysis: One-Pot Direct Strategy to Enantiopure α,β-Disubstituted γ-Butyrolactones

A simple and efficient approach to enantioenriched α,β-disubstituted γ-butyrolactones has been developed through multifunctional modular organocatalysis in a highly enantioselective (>99% ee) and diastereoselective (>30:1) manner following a one-pot sequential Michael-hemiacetalization-oxidation reaction. The catalytic process has great substrate compatibility, and the products have been transformed to synthetically useful molecules. The methodology has also been applied to the formal synthesis of (+)-Pilocarpine.

Magnetic nanoparticles as a catalyst vehicle for simple and easy recycling

The surface of magnetic ferrite nanoparticles (CoFe2O4) was coated with a Rh-based cationic complex, [Rh(cod)(η6-benzoic acid)]BF4, to make them homogeneously dispersable and thermodynamically stable without an

A practical procedure for the synthesis of multifunctional aldehydes through the Fukuyama reduction and elucidation of the reaction site and mechanism

A highly efficient heterogeneous Pd/C catalyst D1 was found to effect the reduction of thiol esters 1 to the corresponding aldehydes 2 with such a low catalyst loading as 0.5-1.0mol%. The chemical properties of the Pd/C catalysts together with the XRF analysis reveal that the reduction is most likely to proceed on the solid surface of the Pd/C catalyst rather than in the solution phase outside the pores. A reaction mechanism through oxidative addition of Pd to the thiol esters 1 was postulated by detection of the oxidative addition intermediate by React IR analysis. A practical purification of 2 was accomplished by conversion to water-soluble bisulfite adducts 7.

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.

Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades

Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.

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.

The first one-pot metathesis-hydroformylation procedure: a straight synthesis of 2-arylpropanals from renewable 1-propenylbenzenes

Hydroformylation is a consolidated synthetic tool in the chemical industry, both in commodity and in the fine chemicals industry. Olefin metathesis has been largely employed in the petrochemical sector, and, more recently, in the synthesis of specialty chemicals. Although these reactions may be involved in the same synthetic route for various industrial chemicals, to the best of our knowledge, they have never been combined in a one-pot procedure. As a proof of concept, we have demonstrated in the present work that the ruthenium-catalyzed ethenolysis of renewable 1-propenylbenzenes followed by the rhodium-catalyzed hydroformylation of functionalized styrenes formed in the first step could be done in one pot. The integration of these reactions was not straightforward once the catalyst of the first step interfered with the catalyst of the second step. Under optimized conditions, it was possible to synthesize 2-arylpropanals, a class of compounds valuable as synthetic intermediates to access non-steroidal anti-inflammatory drugs, in overall yields of 85-90%, at low catalyst loadings.

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.).

Catalytic δ-hydroxyalkynone rearrangement in the stereoselective total synthesis of centrolobine, engelheptanoxides A and C and analogues

A catalytic stereoselective total synthesis of centrolobine and engelheptanoxides A and C has been completed via a metal-free catalytic δ-hydroxyalkynone rearrangement to 2,3-dihydro-4H-pyran-4-one and diastereoselective hydrogenation to the all syn-2,4,6-trisubstituted pyran strategy. The onliest required chirality was introduced by Jacobsen kinetic resolution, which further directed the diastereoselective hydrogenation. A first stereoselective synthesis of engelheptanoxide A is also accomplished. The analogues and derivatives of centrolobine and engelheptanoxides prepared were evaluated for antitubercular activity against M. tuberculosis H37Rv ATCC 27294.