55514-48-2

Usage

Uses

Used in Food and Beverage Industry:
Ethyl 2-methyl-2-butenoate is used as a flavoring agent for its fruity and sweet odor, enhancing the taste and aroma of various food and beverage products.
Used in Perfumes and Cosmetics Industry:
Ethyl 2-methyl-2-butenoate is used as a fragrance ingredient in perfumes and cosmetics, providing a pleasant aroma to these products.
Used in Organic Synthesis:
Ethyl 2-methyl-2-butenoate is used as a precursor in organic synthesis, contributing to the production of various compounds.

InChI:InChI=1/C7H12O2/c1-4-6(3)7(8)9-5-2/h4H,5H2,1-3H3

Upstream product

• 3070-65-3 ethyl 2-methylenebutyrate 
• 29820-55-1 Bicyclo<1.1.0>butan-1-carbonsaeure-ethylester 
• 81171-50-8 (2-Chloro-1-ethoxy-2,3-dimethyl-cyclopropoxy)-trimethyl-silane 
• 74-96-4 ethyl bromide 
• 75-03-6 ethyl iodide 
• 139564-43-5 Aethyl-3-acetoxy-2-methylbutyrat 
• 66069-77-0 (E)-3-bromo-2-methyl-but-2-enoyl chloride 
• 91-22-5 quinoline 
• 5398-71-0 2-bromo-2-ethyl-2-methyl acetic acid ethyl ester 
• 80-59-1 Tiglic acid 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 873421-51-3 3-methyl-hexane-2,4,4-tricarboxylic acid triethyl ester 
• 141-52-6 sodium ethanolate 

Downstream Products

• 41159-39-1 6,6,12,12-Tetrakis(trifluormethyl)-6,12-dihydrodibenzo<1,5>-naphthyridin 
• 565-78-6 3,4-dimethyl-2-pentanone 
• 3354-39-0 4,5-dimethyl-1,2-dithiole-3-thione 
• 55514-49-3 ethyl (E)-γ-bromo-α-methylbut-2-enoate 
• 62097-05-6 ethyl (E)-2-(bromomethyl)but-2-enoate 
• 37715-41-6 2,3-Dimethyl-4,6-dioxo-<1-14C>-cyclohexancarbonsaeureethylester 
• 114996-08-6 ethyl 2-methyl-5-hydroxy-5-phenyl-2-pentenoate 
• 74826-91-8 4-(2-Isocyano-phenyl)-2,3-dimethyl-butyric acid ethyl ester 
• 16509-44-7 ethyl (Z)-2-methyl-2-butenoate 
• 161152-65-4 (Z)-3-Methyl-1-phenyl-pent-3-en-1-one 
• 57253-29-9 3-bromo-2-methyl-1-methyl-1-propene 

Relevant academic research and scientific papers

Asymmetric synthesis of α,β-substituted γ-amino acids via conjugate addition

The first conjugate addition reaction of organocuprates to N-enoyl oxazolidinone where a N-protected γ-nitrogen atom and an α-methyl group are present into α, β-unsaturated system is described. This reaction gave anti-products in moderate yields and high diastereomeric ratios. The anti-products have two contiguous stereogenic centers, one formed by the conjugate addition reaction and the other by a diastereoselective protonation reaction. The removal of chiral oxazolidinone moiety and N-deprotection of amino group furnished chiral α, β-disubstituted γ-amino acids.

Catalytic Asymmetric Vinylogous Mukaiyama-Aldol (CAVM) reactions: The enolate activation

The Catalytic Asymmetric Vinylogous Mukaiyama (CAVM) reactions of various aldehydes with dienolate 1 using different enolate activations (CuF·(S)-TolBinap, t-BuOCu·(S)-Tol-Binap, and various chiral nonracemic ammonium fluorides derived from cinchona alkal

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones

Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.

Asymmetric Aza-Wacker-Type Cyclization of N-Ts Hydrazine-Tethered Tetrasubstituted Olefins: Synthesis of Pyrazolines Bearing One Quaternary or Two Vicinal Stereocenters

We have developed an asymmetric aza-Wacker-type cyclization of N-Ts hydrazine-tethered tetrasubstituted olefins, affording optically active pyrazolines bearing chiral tetrasubstituted carbon stereocenters. This reaction is tolerant to a broad range of substrates under mild reaction conditions, giving the desired chiral products with high enantioselectivities. Generation of two vicinal stereocenters on the C=C double bonds was also achieved with high selectivities, a process which has been rarely studied for Wacker-type reactions. A mechanistic study revealed that this aza-Wacker-type cyclization undergoes a syn-aminopalladation process. It was also found that for substrates bearing two linear alkyl substituents on the outer carbon atom of the olefin, both of which are larger than a methyl group, the alkyl substituent that is cis to the intranucleophilic group participates more readily in β-hydride elimination. When one of the two alkyl substituents on the outer carbon atom of the olefin is a methyl group, β-hydride elimination proceeds selectively at the methylene side, thus both diastereomers can be prepared via switching the configuration of the olefin. Furthermore, the product can be converted to a pharmaceutical compound in high yields over three steps.

2-alkyl substituted crotonic acid and ester synthesis method thereof

The invention provides a 2-alkyl substituted crotonic acid and an ester synthesis method thereof.The ester synthesis methodincludes the following steps that 2-alkyl butyric acid, a first catalyst and halogen are used as raw materials to synthesize 2-halogeneated-alkyln-butyric acid; the 2-halogeneated-alkyln-butyric acid, a solvent and inorganic base are used as raw materials to synthesize 2-alkyl crotonic acid; the 2-alkyl crotonic acid, a second catalyst and alcohol are used as raw materials to synthesize 2-alkyl crotonic acid ester. The 2-alkyl substituted crotonic acid and the ester synthesis method have the advantages that the solvents used in all reaction steps are recyclable, a water phase is recycled after finished product filtering, no wastewater is discharged, and a byproduct haloid acid (particularly referring to hydrobromic acid and hydrochloric acid) is obtained after halogen hydridetail gas is absorbed.

Highly enantioselective iridium-catalyzed hydrogenation of α,β-unsaturated esters

α,β-Unsaturated esters have been employed as substrates in iridium-catalyzed asymmetric hydrogenation. Full conversions and good to excellent enantioselectivities (up to 99 % ee) were obtained for a broad range of substrates with both aromatic- and aliphatic substituents on the prochiral carbon. The hydrogenated products are highly useful as building blocks in the synthesis of a variety of natural products and pharmaceuticals. Asymmetric hydrogenation: A variety of α,β-unsaturated esters were hydrogenated with high enantioselectivities (see scheme). The hydrogenated products have been used in synthetic transformations as well as in formal total syntheses. Copyright

Rh-catalyzed asymmetric hydroformylation of functionalized 1,1-disubstituted olefins

The first method for the highly enantioselective rhodium-catalyzed hydroformylation of 1,1-disubstituted olefins has been developed. By employing either of the P-chirogenic phosphine ligands BenzP* and QuinoxP*, linear aldehydes with β-chirality can be prepared in a highly enantioselective fashion with good chemo- and regioselectivities.

Efficient preparation of α,α-dialkyl-α-(phenylselanyl) acetates and α,β-unsaturated esters from the corresponding α,α-dialkyl-α-cyanoacetates by a lithium naphthalenide induced reductive selenenylation process

An array of α,α-dialkyl-α-(phenylselanyl)acetates has been synthesized very efficiently from readily available α,α- dialkyl-α-cyanoacetates, by use of lithium naphthalenide induced reductive α-selenenylation as a key operation. Moreover, the selanyl esters thus generated in situ could be converted further, in a one-pot treatment with hydrogen peroxide and acetic acid, into the corresponding α,β- unsaturated esters in moderate to high yields. The C=C bond formation was highly regio- and/or diastereoselective in some cases. Georg Thieme Verlag Stuttgart.

A concise synthesis of siphonodictidine

Siphonodictidine (1) has been synthesized for the first time in a concise and regiocontrolled manner by using 2-(tert-butyldimethylsiloxy)-3-methylfuran (6) as the crucial building block. The silver trifluoro-acetate-induced alkylation of 6 with Ω-bromogeranyl acetate 7 gave the key γ-lactone intermediate 8, which on subsequent reduction, conversion of the hydroxyl into the amino group, and amidination afforded siphonodictidine (1) in an overall yield of 25.7% from 6.