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Usage

Uses

Used in Flavor and Fragrance Industry:
(R)-methyl(3,4-dimethoxyphenyl)methanol is used as a flavoring agent for imparting a vanilla-like aroma and taste to various products in the food, beverage, and pharmaceutical industries. Its natural and pleasant scent makes it a popular choice for enhancing the sensory experience of these products.
Used in Antimicrobial Applications:
In the field of antimicrobial applications, (R)-methyl(3,4-dimethoxyphenyl)methanol is used for its potential to inhibit the growth of microorganisms. This property can be beneficial in various industries, such as food preservation and pharmaceuticals, to maintain product quality and safety.
Used in Antioxidant Applications:
(R)-methyl(3,4-dimethoxyphenyl)methanol is also used as an antioxidant, which can help prevent the oxidation of other compounds, thereby extending the shelf life of products and maintaining their freshness. This application is particularly relevant in the food and pharmaceutical industries, where oxidation can lead to spoilage and degradation of active ingredients.

Upstream product

• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 6380-23-0 3,4-dimethoxystyrene 
• 5653-65-6 1-(3,4-dimethoxyphenyl)ethanol 

Relevant academic research and scientific papers

Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes

The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.

Manganese catalyzed asymmetric transfer hydrogenation of ketones

The asymmetric transfer hydrogenation (ATH) of a wide range of ketones catalyzed by manganese complex as well as chiral PxNy-type ligand under mild conditions was investigated. Using 2-propanol as hydrogen source, various ketones could be enantioselectively hydrogenated by combining cheap, readily available [MnBr(CO)5] with chiral, 22-membered macrocyclic ligand (R,R,R',R')-CyP2N4 (L5) with 2 mol% of catalyst loading, affording highly valuable chiral alcohols with up to 95% ee.

C1-Symmetric PNP Ligands for Manganese-Catalyzed Enantioselective Hydrogenation of Ketones: Reaction Scope and Enantioinduction Model

A family of ferrocene-based chiral PNP ligands is reported. These tridentate ligands were successfully applied in Mn-catalyzed asymmetric hydrogenation of ketones, giving high enantioselectivities (92%～99% ee for aryl alkyl ketones) as well as high efficiencies (TON up to 2000). In addition, dialkyl ketones could also be hydrogenated smoothly. Manganese intermediates that might be involved in the catalytic cycle were analyzed. DFT calculation was carried out to help understand the chiral induction model. The Mn/PNP catalyst could discriminate two groups with different steric properties by deformation of the phosphine moiety in the flexible 5-membered ring.

A Ferrocene-Based NH-Free Phosphine-Oxazoline Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones

A new type of ferrocene-based phosphine-oxazoline ligand has been prepared over a few simple steps. An iridium complex of this ligand is air stable and exhibits excellent performance for the asymmetric hydrogenation of simple ketones (up to 98% yield, up to 99% ee, and 20?000 S/C). Exo-α,β-unsaturated cyclic ketones could be regiospecifically hydrogenated to give chiral allylic alcohols with good results. This study indicates that P,N-ligands can also efficiently promote Ir-catalyzed asymmetric hydrogenation without NH-hydrogen-bonding assistance.

Chiral terpene auxiliaries III: Spiroborate esters from (1R,2S,3R,5R)-3-amino-apopinan-2-ol as highly effective catalysts for asymmetric reduction of ketones with borane

New spiroborate esters, derived from terpene amino alcohols, (S)-prolinol, and 2-aminoethanol, were employed as catalysts in the borane reduction of acetophenone and other aryl alkyl and halogenated ketones. The corresponding alcohols were obtained in high yields and with enantioselectivities up to 98% ee. The influence of the amino alcohol and the diol moieties of spiroborate on the reaction selectivity was examined. The catalyst load, the nature of the solvent, the borane source, and the reaction conditions were also investigated.

Iron catalyzed asymmetric hydrogenation of ketones

Chiral molecules, such as alcohols, are vital for the manufacturing of fine chemicals, pharmaceuticals, agrochemicals, fragrances, and novel materials. These molecules need to be produced in high yield and high optical purity and preferentially catalytically. Among all the asymmetric catalytic reactions, asymmetric hydrogenation with H2 (AH) is the most widely used in the industry. With few exceptions, these AH processes use catalysts based on the three critical metals, rhodium, ruthenium, and iridium. Herein we describe a simple, industrially viable iron catalyst that allows for the AH of ketones, a process currently dominated by ruthenium and rhodium catalysts. By combining a chiral, 22-membered macrocyclic ligand with the cheap, readily available Fe 3(CO)12, a wide variety of ketones have been hydrogenated under 50 bar H2 at 45-65 C, affording highly valuable chiral alcohols with enantioselectivities approaching or surpassing those obtained with the noble metal catalysts. In contrast to AH by most noble metal catalysts, the iron-catalyzed hydrogenation appears to be heterogeneous.

Enhancement of enantioselectivity by alcohol additives in asymmetric hydrogenation with bis(oxazolinyl)phenyl ruthenium catalysts

Bis(oxazolinyl)phenyl ruthenium(ii) complexes were found to catalyze asymmetric hydrogenation of ketones, in which chiral bulky alcohol additives showed significant enhancement of enantioselectivity even in protic solvents. The Royal Society of Chemistry 2012.

Iron- and cobalt-catalyzed asymmetric hydrosilylation of ketones and enones with bis(oxazolinylphenyl)amine ligands

Chiral bis(oxazolinylphenyl)amines proved to be efficient auxiliary ligands for iron and cobalt catalysts with high activity for asymmetric hydrosilylation of ketones and asymmetric conjugate hydrosilylation of enones.

A flexible route to chiral 2-endo-substituted 9-oxabispidines and their application in the enantioselective oxidation of secondary alcohols

A new and flexible route to enantiomerically pure bi-and tricyclic 9-oxabispidines has been developed with use of (1R,5S)-7-methyl-2-oxo-9-oxa-3,7- diazabicyclo[33.1]nonane-3-carboxylic acid tert-butyl ester as the common late-stage intermediate. The 9-oxabispidines synthesized were evaluated as the chiral ligands in the Pd(II)-catalyzed oxidative kinetic resolution of secondary alcohols giving good to excellent selectivity factors of up to 19.

Nonpeptide urotensin-II receptor antagonists: A new ligand class based on piperazino-phthalimide and piperazino-isoindolinone subunits

We have discovered two related chemical series of nonpeptide urotensin-II (U-II) receptor antagonists based on piperazino-phthalimide (5 and 6) and piperazino-isoindolinone (7) scaffolds. These structure types are distinctive from those of U-II receptor antagonist series reported in the literature. Antagonist 7a exhibited single-digit nanomolar potency in rat and human cell-based functional assays, as well as strong binding to the human U-II receptor. In advanced pharmacological testing, 7a blocked the effects of U-II in vitro in a rat aortic ring assay and in vivo in a rat ear-flushmodel. Adiscussion of U-II receptor antagonist pharmacophores is presented, and a specifically defined model is suggested from tricycle 13, which has a high degree of conformational constraint.