1575-74-2

Usage

Uses

Used in Flavor Industry:
2-METHYL-4-PENTENOIC ACID is used as a raw material for fruit flavor, particularly enhancing the fruity fragrances in various products. Its natural, cheese-like odor adds a unique and appealing scent to the final product, making it a valuable component in the creation of diverse flavor profiles.
Used in Fragrance Industry:
In the fragrance industry, 2-METHYL-4-PENTENOIC ACID is used as an enhancer of fruity fragrances, contributing to the development of complex and long-lasting scents. Its ability to add depth and character to fragrances makes it a sought-after ingredient in the formulation of perfumes, colognes, and other scented products.

Synthesis Reference(s)

Chemistry Letters, 9, p. 571, 1980Tetrahedron Letters, 21, p. 2181, 1980 DOI: 10.1016/S0040-4039(00)78992-1

InChI:InChI=1/C6H10O2/c1-3-4-5(2)6(7)8/h3,5H,1,4H2,2H3,(H,7,8)/p-1/t5-/m1/s1

Upstream product

• 4441-96-7 3-Methyl-2-carboxy-penten-⁽⁴⁾-saeure 
• 3508-78-9 3-allyl-2,4-pentanedione 
• 5281-63-0 2-Allyl-2-methylmalonic acid 
• 53651-72-2 diethyl allylmethylmalonate 
• 107-05-1 3-chloroprop-1-ene 
• 609-08-5 Diethyl methylmalonate 
• 1823-54-7 α-methyl-β-propiolactone 
• 1826-67-1 vinyl magnesium bromide 
• 802294-64-0 propionic acid 
• 106-95-6 allyl bromide 
• 107-18-6 allyl alcohol 
• 115-80-0 Triethyl orthopropionate 
• 98-89-5 Cyclohexanecarboxylic acid 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 26118-97-8 2-allyl-3-pentanone 
• 53399-81-8 ethyl 2-methyl-4-pentenoate 
• 1949-38-8 α-Methyl-γ-phenyl-valeriansaeure 
• 33982-85-3 1-(2,3-dihydro-1H-inden-2-yl)ethanone 
• 88708-25-2 C₁₃H₁₆Cl₂O₃Te 
• 107971-37-9 (tetrahydro-4-methyl-5-oxofuran-2-yl)methyl 4-methylbenzenesulfonate 
• 112238-67-2 3-methyl-5-((phenylselanyl)methyl)dihydrofuran-2(3H)-one 
• 145051-45-2 3-benzoyl-1-diazo-3-methyl-2-oxo-5-hexene 
• 792921-52-9 2-methyl-pent-4-enoic acid (2,4,5-trimethoxy-3-tridec-12-enyl-phenyl)-amide 
• 141192-61-2 (+/-)-2-methylpent-4-enoic acid benzylamide 

Relevant academic research and scientific papers

Synthesis of S-(+)-4-methyl-3-heptanone, the principal alarm pheromone of Atta texana, and its enantiomer

The principal alarm pheromone of Atta texana S-(+)-4-methyl-3-heptanone, and its enantiomer have been prepared synthetically in high optical purity.

Why do thioureas and squaramides slow down the Ireland–Claisen rearrangement?

A range of chiral hydrogen-bond-donating organocatalysts was tested in the Ireland–Claisen rearrangement of silyl ketene acetals. None of these organocatalysts was able to impart any enantioselectivity on the rearrangements. Furthermore, these organocatalysts slowed down the Ireland–Claisen rearrangement in comparison to an uncatalyzed reaction. The catalyst-free reaction proceeded well in green solvents or without any solvent. DFT calculations showed that the activation barriers are higher for reactions involving hydrogen-donating organocatalysts and kinetic experiments suggest that the catalysts bind stronger to the starting silyl ketene acetals than to transition structures thus leading to inefficient rearrangement reactions.

Synthesis of 5-[(Pentafluorosulfanyl)methyl]-γ-butyrolactones via a Silver-Promoted Intramolecular Cyclization Reaction

The synthesis of 5-[(pentafluorosulfanyl)methyl]-γ-butyrolactones bearing different substituents at position 3 or 4 is reported. A silver-promoted intramolecular cyclization of substituted 4-chloro-5-(pentafluorosulfanyl)pentanoic acids allows the preparation of the substituted SF5-containing γ-butyrolactones in up to 96 % yield.

Copper(II)-Catalyzed Alkene Aminosulfonylation with Sodium Sulfinates for the Synthesis of Sulfonylated Pyrrolidones

A copper-catalyzed direct aminosulfonylation of unactivated alkenes with sodium sulfinates for the efficient synthesis of sulfonylated pyrrolidones is described. This reaction features good functional group tolerance and wide substrate scope, providing an efficient and straightforward protocol to access this kind of pyrrolidones. Moreover, preliminary mechanistic investigations disclosed that a free-radical pathway might be invovled in the process.

Direct oxidative lactonization of alkenoic acids mediated solely by NaIO4: Beyond a simple oxidant

Triflic acid-catalyzed direct oxidative lactonization of alkenoic acids mediated solely by NaIO4 without halogen salts is described. Sodium periodate works not only as an oxidant, but also as an active reagent and directly mediates the lactonization. A new cheap, green, and practical oxidative lactonization approach has been developed using NaIO4 as the sole reagent.

Synthesis of Enantiomerically Enriched 2-Hydroxymethylalkanoic Acids by Oxidative Desymmetrisation of Achiral 1,3-Diols Mediated by Acetobacter aceti

The stereoselective desymmetrisation of achiral 2-alkyl-1,3-diols is performed by oxidation of one of the two enantiotopic primary alcohol moieties by means of Acetobacter aceti MIM 2000/28 to afford the corresponding chiral 2-hydroxymethyl alkanoic acids (up to 94 % ee). The procedure, carried out in aqueous medium under mild conditions of pH, temperature and pressure, contributes to enlarge the portfolio of enzymatic oxidations available to organic chemists for the development of sustainable manufacturing processes.

N -Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/br?nsted acid Co-catalyzed allylic C-H oxidation

A Pd(II)/bis-sulfoxide/Br?nsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and π-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.

Use of ethyl (benzothiazol-2-ylsulfonyl)acetate for malonic ester-type syntheses of carboxylic acids and esters

A new methodology for the synthesis of substituted carboxylic acids is described. Alkylation of either ethyl (benzothiazol-2-ylsulfonyl)acetate or ethyl 2-(benzothiazol-2-ylsulfonyl)propionate was achieved with alkyl halides and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane solution. These products were then desulfinated and hydrolysed in one-pot under mild conditions to give substituted acetic acids in good-to-excellent yields.

Total synthesis of (+)-(2′S,3′R)-zoapatanol exploiting the B-alkyl Suzuki reaction and the nucleophilic potential of the sulfinyl group

A stereoselective synthesis of the diterpenoid oxepane (+)-zoapatanol is described. The key steps include a B-alkyl Suzuki cross-coupling reaction for the stereoselective synthesis of trisubstituted alkenes, creation of the two stereogenic centers on the oxepane ring by heterofunctionalization of an alkene through substrate control exploiting the nucleophilic potential of an intramolecular sulfinyl group, and transformation of a β-hydroxy sulfoxide into a terminal alkene. Copyright

Palladium-catalyzed allylic alkylation of doubly deprotonated carboxylic acids

Doubly deprotonated carboxylic acids undergo smooth palladium-catalyzed carbon alkylations with the allylic substrates methyl allyl carbonate and (E)-methyl (pent-3-en-2-yl) carbonate to give γ,δ-unsaturated carboxylic acids. A diastereoselective and enantioselective protocol leads to (2S,3R)-hexenoic acid in 87% ee. Copyright