2177-77-7

Usage

Uses

Used in Flavor and Fragrance Industry:
METHYL 2-METHYLPENTANOATE is used as a flavoring agent for its sweet fruity, maple, hazelnut, and strawberry odor. Its unique taste and aroma make it a popular choice for enhancing the flavor of various food products, such as baked goods, beverages, and confectioneries.
Used in Perfumery:
METHYL 2-METHYLPENTANOATE is used as a fragrance ingredient due to its pleasant and versatile scent. It can be used to create a wide range of fragrances, from fruity and green apple to more complex and sophisticated scents, making it a valuable addition to the perfumer's palette.
Used in the Cosmetic Industry:
METHYL 2-METHYLPENTANOATE is used as a component in the formulation of cosmetics, such as lotions, creams, and body care products, for its pleasant and appealing scent. Its ability to provide a sweet fruity, maple, hazelnut, and strawberry odor enhances the sensory experience of these products, making them more appealing to consumers.
Used in the Pharmaceutical Industry:
METHYL 2-METHYLPENTANOATE can be used as an additive in the pharmaceutical industry to improve the taste and aroma of medications, making them more palatable for patients. Its distinct flavor profile can help mask unpleasant tastes, improving patient compliance and overall experience with medication.

InChI:InChI=1/C7H14O2/c1-4-5-6(2)7(8)9-3/h6H,4-5H2,1-3H3/t6-/m1/s1

Upstream product

• 64-67-5 diethyl sulfate 
• 408538-16-9 1,1-dimethoxy-pent-1-ene 
• 77-78-1 dimethyl sulfate 
• 20459-96-5 2-Methyl-4-pentensaeuremethylester 
• 80-62-6 methacrylic acid methyl ester 
• 67-56-1 methanol 
• 1575-74-2 (+-)-2-methyl-pent-4-enoic acid 
• 109-67-1 1-penten 
• 201230-82-2 carbon monoxide 
• 53531-14-9 (R)-(+)-2-methylpentanal 
• 82043-22-9 (S)-(-)-2-methylpentanal 
• 97-61-0 2-Methylpentanoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 123-15-9 2-methylvaleraldehyde 

Downstream Products

• 67-56-1 methanol 
• 97-61-0 2-Methylpentanoic acid 
• 94759-84-9 2-Methyl-1,1-bis-(4-methoxy-phenyl)-penten-⁽¹⁾ 
• 105-30-6 2-methylpentan-1-ol 
• 95164-83-3 2-Methyl-1,1-bis-(4-acetoxy-phenyl)-penten-⁽¹⁾ 
• 39255-48-6 2-Methyl-1,1-bis-(4-hydroxy-phenyl)-penten-⁽¹⁾ 

Relevant academic research and scientific papers

C?Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3-Enynes

A new family of carbon-bound boron enolates, generated by a kinetically controlled halogen exchange between chlorocatecholborane and silylketene acetals, is described. These C?boron enolates are demonstrated to activate 1,3-enyne substrates in the presence of a Pd0/Senphos ligand complex, resulting in the first examples of a carboboration reaction of an alkyne with enolate-equivalent nucleophiles. Highly substituted dienyl boron building blocks are produced in excellent site-, regio-, and diastereoselectivity by the described catalytic cis-carboboration reaction.

A biocatalytic method for the chemoselective aerobic oxidation of aldehydes to carboxylic acids

Herein, we present a study on the oxidation of aldehydes to carboxylic acids using three recombinant aldehyde dehydrogenases (ALDHs). The ALDHs were used in purified form with a nicotinamide oxidase (NOx), which recycles the catalytic NAD+ at the expense of dioxygen (air at atmospheric pressure). The reaction was studied also with lyophilised whole cell as well as resting cell biocatalysts for more convenient practical application. The optimised biocatalytic oxidation runs in phosphate buffer at pH 8.5 and at 40 °C. From a set of sixty-one aliphatic, aryl-Aliphatic, benzylic, hetero-Aromatic and bicyclic aldehydes, fifty were converted with elevated yield (up to >99%). The exceptions were a few ortho-substituted benzaldehydes, bicyclic heteroaromatic aldehydes and 2-phenylpropanal. In all cases, the expected carboxylic acid was shown to be the only product (>99% chemoselectivity). Other oxidisable functionalities within the same molecule (e.g. hydroxyl, alkene, and heteroaromatic nitrogen or sulphur atoms) remained untouched. The reaction was scaled for the oxidation of 5-(hydroxymethyl)furfural (2 g), a bio-based starting material, to afford 5-(hydroxymethyl)furoic acid in 61% isolated yield. The new biocatalytic method avoids the use of toxic or unsafe oxidants, strong acids or bases, or undesired solvents. It shows applicability across a wide range of substrates, and retains perfect chemoselectivity. Alternative oxidisable groups were not converted, and other classical side-reactions (e.g. halogenation of unsaturated functionalities, Dakin-Type oxidation) did not occur. In comparison to other established enzymatic methods such as the use of oxidases (where the concomitant oxidation of alcohols and aldehydes is common), ALDHs offer greatly improved selectivity.

Branched Selectivity in the Pd-Catalysed Methoxycarbonylation of 1-Alkenes

The methoxycarbonylation of alkenes by palladium(II) complexes with P,O-donor ligands [(2-methoxyphenyl)diphenylphosphine (L-2), bis(2-methoxyphenyl) phenyl phosphine (L-3) and tris(2-methoxyphenyl) phosphine (L-4)] has been investigated. The results show that the Pd complexes derived from these ligands provide high regioselectivity for the branched esters from 1-pentene and 1-hexene (>80 %). Various parameters (including temperature, pressure, acid concentration) were optimized to improve the performance of the catalyst system. Higher temperatures afforded higher regioselectivity; but effected rapid catalyst decomposition. Acceptable turnover frequencies, conversions as well as catalyst stability could be obtained at higher L/Pd ratios. The dramatic change in regioselectivity is rationalised on the basis of the hemi-lability of the o-methoxy moiety, which may lead to ligand dissociation from L2PdX2 (L=ligand, X=Cl) rather than the expected dissociation of X. In support of our hypothesis, direct evidence for the coordination of the o-methoxy to the Pd centre was demonstrated by the crystal structure. To the best of our knowledge, this work provides the first reported route to valuable branched esters through the methoxycarbonylation of alkenes at suitable rates.

The scope and mechanism of palladium-catalysed Markovnikov alkoxycarbonylation of alkenes

Hydroesterification reactions represent a fundamental type of carbonylation reaction and constitute one of the most important industrial applications of homogeneous catalysis. Over the past 70 years, numerous catalyst systems have been developed that allow for highly linear-selective (anti-Markovnikov) reactions and are used in industry to produce linear carboxylates starting from olefins. In contrast, a general catalyst system for Markovnikov-selective alkoxycarbonylation of aliphatic olefins remains unknown. In this paper, we show that a specific palladium catalyst system consisting of PdX2/N-phenylpyrrole phosphine (X, halide) catalyses the alkoxycarbonylation of various alkenes to give the branched esters in high selectivity (branched selectivity up to 91%). The observed (and unexpected) selectivity has been rationalized by density functional theory computation that includes a dispersion correction.

Systematic methodology for the development of biocatalytic hydrogen-borrowing cascades: Application to the synthesis of chiral α-substituted carboxylic acids from α-substituted α,β-unsaturated aldehydes

Ene-reductases (ERs) are flavin dependent enzymes that catalyze the asymmetric reduction of activated carbon-carbon double bonds. In particular, α,β-unsaturated carbonyl compounds (e.g. enals and enones) as well as nitroalkenes are rapidly reduced. Conversely, α,β-unsaturated esters are poorly accepted substrates whereas free carboxylic acids are not converted at all. The only exceptions are α,β-unsaturated diacids, diesters as well as esters bearing an electron-withdrawing group in α- or β-position. Here, we present an alternative approach that has a general applicability for directly obtaining diverse chiral α-substituted carboxylic acids. This approach combines two enzyme classes, namely ERs and aldehyde dehydrogenases (Ald-DHs), in a concurrent reductive-oxidative biocatalytic cascade. This strategy has several advantages as the starting material is an α-substituted α,β-unsaturated aldehyde, a class of compounds extremely reactive for the reduction of the alkene moiety. Furthermore no external hydride source from a sacrificial substrate (e.g. glucose, formate) is required since the hydride for the first reductive step is liberated in the second oxidative step. Such a process is defined as a hydrogen-borrowing cascade. This methodology has wide applicability as it was successfully applied to the synthesis of chiral substituted hydrocinnamic acids, aliphatic acids, heterocycles and even acetylated amino acids with elevated yield, chemo- and stereo-selectivity. A systematic methodology for optimizing the hydrogen-borrowing two-enzyme synthesis of α-chiral substituted carboxylic acids was developed. This systematic methodology has general applicability for the development of diverse hydrogen-borrowing processes that possess the highest atom efficiency and the lowest environmental impact. This journal is

Aluminum triflate as a highly active and efficient nonprotic cocatalyst in the palladium-catalyzed methoxycarbonylation reaction

(Chemical Equation Presented) Lewis does it better: Aluminum triflate readily replaces Bronsted acid cocatalysts in the palladium-catalyzed methoxycarbonylation reaction of styrene and 1-pentene, producing catalysts that are stable and more active than those using traditional acids. Catalyst loadings of 0.02% allow conversions of up to 100% to be achieved within three hours with no loss of linear/branched ester selectivity.

Catalytic synthesis of oxygenate from alcohol

The present invention discloses a method for catalytic synthesis of oxygenate from alcohol. At first, a feeding material comprising at least one alcohol is provided. Next, a copper-containing catalyst is provided and the catalyst further comprises at least one metal element selected from the group consisting of the following: zinc, magnesium, and aluminum elements. Following that, a catalytic reaction of the feeding material over the copper-containing catalyst is carried out to synthesize at least one oxygenate.

Tetramethylammonium phenyltrialkylborates in the photoinduced electron transfer reaction with benzophenone. Generation of alkyl radicals and their addition to activated alkenes

Photoinduced one electron oxidation of tetramethylammonium phenyltrialkylborates by the excited state of benzophenone in an acetonitrile/benzene solution containing an excess of activated alkene produces substantially more than one equivalent of the alkyl radicals. The corresponding adducts of alkyl radicals to the alkenes are produced in good yields. No phenyl radical adducts are observed.

Oxidative Rearrangement of Alkynes to Carboxylic Acid Esters by benzene in Methanol

A direct synthesis of methyl aryl alkanoate via oxidative rearrangement of alkynes using benzene in methanol is described.

Selective carbonylation of olefinically unsaturated hydrocarbons using palladium-arsine or -stibine catalysts

A carbonylation process is provided for conversion of olefinically unsaturated hydrocarbons to a mixture of esters or acids with a high ratio of iso:normal ester or acid by reaction with carbon monoxide and a hydroxylic compound, said process being carried out in the absence of added hydrogen or oxygen and in the presence of a palladium salt complexed with an arsine or stibine ligand as catalyst; 2-10 additional moles of arsine or stibine ligand per mole of catalyst may be present in said process to further enhance the ratio of iso:normal product and to promote catalyst stability. The catalyst, for example, may be palladium dichloride bis(triphenylarsine) or palladium dichloride bis(tri-p-tolyl arsine).