51424-01-2

Usage

Uses

Used in Food and Beverage Industry:
2-Hexenoic acid, 5-methyl-, (E)is used as a flavoring ingredient in the food and beverage industry. Its unique combination of fruity, fatty, and garlic-like notes adds depth and complexity to a wide range of products, enhancing their taste and aroma.
Used in Perfume and Cosmetics Production:
In the perfume and cosmetics industry, 2-Hexenoic acid, 5-methyl-, (E)is utilized for its distinctive scent profile. It contributes to the creation of various fragrances and helps in formulating unique and appealing cosmetic products.
Used in Pharmaceutical and Personal Care Products:
2-Hexenoic acid, 5-methyl-, (E)has been studied for its potential antimicrobial and antifungal properties. This makes it a promising candidate for use in pharmaceutical and personal care products, where it can help combat harmful microorganisms and support overall hygiene and health.

Upstream product

• 20859-10-3 (3E)-6-methylhept-3-en-2-one 
• 628-46-6 5-methylhexanoic acid 
• 590-86-3 isovaleraldehyde 
• 141-82-2 malonic acid 
• 75513-56-3 (E)-methyl 5-methyl-2-hexenoate 
• 1006691-39-9 (S)-2-(9-fluorenylmethoxycarbonyloxy)-4-methylpentanoic acid 
• 904891-61-8 Carbonic acid (S)-1-(2-diazo-acetyl)-3-methyl-butyl ester 9H-fluoren-9-ylmethyl ester 
• 904891-65-2 (S)-1-diazo-3-hydroxy-5-methylhexan-2-one 
• 631-64-1 dibromoacetic acid 
• 34993-63-0 ethyl (E)-5-methylhex-2-enoate 

Downstream Products

• 75513-56-3 (E)-methyl 5-methyl-2-hexenoate 
• 370064-66-7 3-(S)-isobutyl-aziridine-2-(R)-carboxylic acid benzyl ester 
• 370064-68-9 3-(S)-isobutyl-1-(4-methoxybenzenesulfonyl)aziridine-2-(R)-carboxylic acid 
• 370064-63-4 (E)-1,5-(S)-dimethyl-3-(5-methylhex-2-enoyl)-4-(R)-phenylimidazolidin-2-one 
• 370064-65-6 1-(3-(S)-isobutyl-aziridine-2-(R)-carbonyl)-3,4-(S)-dimethyl-5-(R)-phenylimidazolidin-2-one 
• 370064-67-8 3-(S)-isobutyl-1-(4-methoxybenzenesulfonyl)aziridine-2-(R)-carboxylic acid benzyl ester 
• 370064-69-0 3-(S)-isobutyl-1-(4-methoxybenzenesulfonyl)aziridine-2-(R)-carboxylic acid benzyloxyamide 
• 1860-39-5 5-methylhexanal 
• 1346518-38-4 tert-butyl (E)-7-methyl-3-oxooct-4-enoate 
• 261896-46-2 (R,E)-3-(5-methylhex-2-enoyl)-4-phenyl-1,3-oxazolidine-2-one 
• 1531586-72-7 (S)-4-methyl-2-(2-oxo-2-((R)-2-oxo-4-phenyloxazolidin-3-yl)ethyl)pentanenitrile 

Relevant academic research and scientific papers

A protocol for accessing the β-azidation of α,β-unsaturated carboxylic acids

This contribution reports the preparation and use of a new immobilized catalyst, PS-DABCOF (9), which has been specifically designed to access for the first time the efficient β-azidation of α,β-unsaturated carboxylic acids.

Ligand-controlled divergent dehydrogenative reactions of carboxylic acids via C–H activation

Dehydrogenative transformations of alkyl chains to alkenes through methylene carbon-hydrogen (C–H) activation remain a substantial challenge. We report two classes of pyridine-pyridone ligands that enable divergent dehydrogenation reactions through palladium-catalyzed b-methylene C–H activation of carboxylic acids, leading to the direct syntheses of a,b-unsaturated carboxylic acids or g-alkylidene butenolides. The directed nature of this pair of reactions allows chemoselective dehydrogenation of carboxylic acids in the presence of other enolizable functionalities such as ketones, providing chemoselectivity that is not possible by means of existing carbonyl desaturation protocols. Product inhibition is overcome through ligand-promoted preferential activation of C(sp3)–H bonds rather than C(sp2)–H bonds or a sequence of dehydrogenation and vinyl C–H alkynylation. The dehydrogenation reaction is compatible with molecular oxygen as the terminal oxidant.

Mechanistic Studies of the Deslongchamps Annulation

The Cs2CO3-mediated annulations ("Deslongchamps annulations") of three spirocyclic benzoquinone monoketals 5b-d with an ester or acyl substituent at C-2 to two tert-butyl esters of λδ-unsaturated β-ketocarboxyl acids ("Nazarov reagents" 2a,b) were monitored 1H NMR spectroscopically. This revealed that a primary product, by all likelihood the Michael adduct, forms fast and prior to the appearance of the Deslongchamps adduct. These primary products form reversibly. This was proved by two crossover and four scavenging experiments. Therein, components already incorporat.

Diasteroselective conjugate addition of diethylaluminum cyanide to a conjugated N -enoyl system: An alternative synthesis of (S)-pregabalin

We have explored in this work the conjugate addition of diethylaluminum cyanide (Nagata's reagent) to an N-enoyl system bearing the (R)-4-phenyl-2- oxazolidinone chiral auxiliary. Since this method provided a practical synthesis of γ-amino acids, we report the conjugate addition of diethylaluminum cyanide as the key step in the synthesis of (S)-pregabalin 1 in a five-step sequence of reactions from commercially available starting materials.

METHOD FOR THE DECARBOXYLATIVE HYDROFORMYLATION OF ALPHA, BETA- UNSATURATED CARBOXYLIC ACIDS

The present invention relates to a process for preparing aldehydes by reacting an α,β-unsaturated carboxylic acid or a salt thereof with carbon monoxide and hydrogen in the presence of a catalyst comprising at least one complex of a metal of transition group VIII of the Periodic Table of the Elements with at least one compound of the formula (I), where Pn is pnicogen; W is a divalent bridging group having from 1 to 8 bridge atoms between the flanking bonds; R1 is a functional group capable of forming at least one intermolecular, noncovalent bond with the —X(═O)OH group of the compound of the formula (I); R2, R3 are each in each case optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl or together with the pnicogen atom and together with the groups Y2 and Y3 if present form an optionally fused and optionally substituted 5- to 8-membered heterocycle; a, b and c are each 0 or 1; and Y1,2,3 are each, independently of one another, O, S, NRa or SiRbRc, where Ra,b,c are each H or in each case optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl; and the use of the above-described catalyst for the decarboxylative hydroformylation of α,β-unsaturated carboxylic acids.

A supramolecular catalyst for the decarboxylative hydroformylation of α,β-unsaturated carboxylic acids

(Chemical Equation Presented) Head 'em up, move 'em out, aldehyde! A catalytic transformation of α,β-unsaturated carboxylic acids into aldehydes through a hydroformylation-decarboxylation process has been developed (see scheme; Do = donor ligand, FG1 and FG2 = complementary functional groups). The reaction proceeds at mild conditions, tolerates many functional groups, and liberates CO2 as the only stoichiometric by-product.

Enantioselective intramolecular hydroarylation of alkenes via directed C-H bond activation

(Chemical Equation Presented) Highly enantioselective catalytic intramolecular ortho-alkylation of aromatic imines containing alkenyl groups tethered at the meta position relative to the imine directing group has been achieved using [RhCl(coe)2]2 and chiral phosphoramidite ligands. Cyclization of substrates containing 1,1- and 1,2-disubstituted as well as trisubstituted alkenes were achieved with enantioselectivities >90% ee for each substrate class. Cyclization of substrates with Z-alkene isomers proceeded much more efficiently than substrates with E-alkene isomers. This further enabled the highly stereoselective intramolecular alkylation of certain substrates containing Z/E-alkene mixtures via a Rh-catalyzed alkene isomerization with preferential cyclization of the Z-isomer.

Homologation of α-hydroxy acids to α-unsubstituted β-hydroxy carboxamides via Arndt-Eistert reaction

Here we studied the homologation of leucic and phenyl lactic acid via Wolff-rearrangement of their diazoketones to the corresponding β-hydroxy acids. This reaction requires distinct conditions to that of their amino acid analogues. The choice of the Oα-substituent can selectively direct the reaction to α-unsubstituted β-hydroxy carboxamides or (E)-α,β-unsaturated carboxamides and offers a new route from α-hydroxy acids to such compounds.

Direct reaction of dibromoacetic acid with aldehydes promoted by samarium diiodide: An easy, efficient, and rapid synthesis of (E)-α,β- unsaturated carboxylic acids with total stereoselectivity

A promoted SmI2 direct reaction of dibromoacetic acid with different aldehydes, followed by an elimination reaction also promoted by samarium diiodide, affords (E)-α,β-unsaturated carboxylic acids 2 with total stereoselectivity. A mechanism to explain this transformation is proposed.

Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the Rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium

The Rodionov reaction of 49 available aliphatic and aromatic aldehydes with malonic acid and ammonium acetate in alcoholic medium, resulting in formation of β-amino acids, propenoic, and ylidenemalonic acids, was studied. Certain regioselectivity regularities of the reaction were revealed. Among the variety of ketones studied, cyclohexanone is the only whose reaction yields a β-amino acid. Unusual dehydrofluorination of 6-chloro-2-fluorocinnamic acid under the Rodionov reaction was discovered. 2005 Pleiades Publishing, Inc.