5837-78-5

Usage

Uses

Used in Flavor and Fragrance Industry:
Ethyl tiglate is used as a flavor and fragrance ingredient for its fruity, caramel odor. It is particularly valued in the creation of artificial fruit flavors and fragrances due to its natural occurrence in various fruits.
Used in Pheromone Research:
In the field of biological research, ethyl tiglate is used as a pheromone for studying the mating behavior and communication of certain Drosophila species. Its role as a male-specific pheromone makes it an important compound for understanding the chemical ecology and reproductive strategies of these insects.
Used in Chemical Synthesis:
Ethyl tiglate is also utilized in the synthesis of other compounds, such as grandisol and fraganol. These synthesized products have their own specific applications in various industries, further expanding the utility of ethyl tiglate as a starting material in chemical synthesis.
Used in the Study of Microbial Metabolism:
The production of ethyl tiglate by Saprochaete suaveolens through the metabolism of isoleucine provides an opportunity for researchers to study the metabolic pathways and capabilities of this microorganism. This knowledge can be applied to develop new biotechnological applications and improve our understanding of microbial processes.

Preparation

By direct esterification of tiglic acid with ethyl alcohol in the presence of concentrated H2SO4 or by reaction of bromomethylethyl acetic acid ethyl ester with dimethylaniline.

InChI:InChI=1/C7H12O2/c1-4-6(3)7(8)9-5-2/h4H,5H2,1-3H3/b6-4+

Upstream product

• 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 
• 565-63-9 Angelic acid 
• 121-69-7 N,N-dimethyl-aniline 
• 77-70-3 α-hydroxy-α-methylbutyric acid ethyl ester 
• 14002-73-4 3-hydroxy-2,2-dimethyl-propionic acid ethyl ester 
• 1647-12-7 ethyl 2-methyl-but-3-enoate 
• 58518-19-7 2-(1-Chloro-ethyl)-2-methyl-malonic acid diethyl ester 
• 75-07-0 acetaldehyde 
• 14273-06-4 1-ethoxy-1-propyne 
• 62097-05-6 ethyl (E)-2-(bromomethyl)but-2-enoate 
• 16509-44-7 ethyl (Z)-2-methyl-2-butenoate 

Downstream Products

• 123-51-3 i-Amyl alcohol 
• 108-64-5 Ethyl isovalerate 
• 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 
• 52050-79-0 1r-benzyl-4c,5t-dimethyl-1-oxo-2ξ-phenyl-1λ⁵-phospholan-3-one 
• 497-02-9 2-methyl-2-buten-1-ol 
• 51263-63-9 Ethyl esters of 4-bromoisoangelic acid + 4-bromoangelic acid 
• 37715-41-6 2,3-Dimethyl-4,6-dioxo-<1-14C>-cyclohexancarbonsaeureethylester 
• 74826-91-8 4-(2-Isocyano-phenyl)-2,3-dimethyl-butyric acid ethyl ester 
• 7452-79-1 ethyl 2-methylbutyrate 
• 16509-44-7 ethyl (Z)-2-methyl-2-butenoate 
• 3070-65-3 ethyl 2-methylenebutyrate 

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.

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.

Synthesis and resolution of 2-methyl analogues of GABA

E-4-Amino-2-methylbut-2-enoic acid, (±)-4-amino-2-methylbutanoic acid, (+)-(S)- and (-)-(R)-4-amino-2-methylbutanoic acid, which are analogues of the inhibitory neurotransmitter GABA (γ-aminobutyric acid, 4-aminobutanoic acid), were synthesised from ethyl 2-methyl-4-phthalimidobut-2- enoate, ethyl 2-methyl-4-phthalimidobutanoate, (+)-[(2R-(3,3-dimethylbutyro-1,4- lactonyl)]-(2S)-methyl-4-phthalimidobutanoate and (-)-[(2R-(3,3-dimethylbutyro- 1,4-lactonyl)]-(2R)-methyl-4-phthalimidobutanoate, respectively. The assignment of the absolute configuration of (+)-(S)- and (-)-(R)-4-amino-2-methylbutanoic acid was based on the X-ray crystallographic structure of the (+)-(R,S)-diastereoisomer, and direct comparison of specific rotations with the published data for (-)-(R)-4-amino-2-methylbutanoic acid.

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.

Structure-cytoprotective activity relationship of simple molecules containing an α,β-unsaturated carbonyl system

In previous reports we attributed the cytoprotective activity of several sesquiterpene lactones to the presence of a nonhindered electrophilic acceptor in their structure. We suggested that the mechanism of protection would be, at least in part, mediated through a reaction between the electrophilic acceptor and the sulfhydryl-containing groups of the mucosa. We report here the gastric cytoprotective effect of simple molecules containing an α,β-unsaturated carbonyl group. In the present paper, we undertake the study of molecular accessibility and molecular shape, in addition to conformational, electronic, and steric factors. Our results helped to establish two important facts connecting chemical structure with cytoprotective effect. Firstly, an adequate molecular accessibility appears to be necessary to produce the biological response, and secondly, the α,β- unsaturated carbonyl system has to be included in a cyclic structure or, at least, in the proximity of a cyclic system.

Stereocontrol of stereogenic centres para on a benzene ring using the SE2″ reaction of a pentadienylsilane

The pentadienylsilane 9 and the dimethyl acetal 2 of isobutyraldehyde react with high (80:20) anti stereospecificity to give largely the diene 10a, which was converted into the Para-disubstituted benzene 11a, having 1,6-related stereogenic centres.

Preparation et etude de nouveaux derives organozinciques allyliques fonctionnels

Stable organozinc compounds derived from alkyl-3-alkyl-2-(bromomethyl)-propenoates have been prepared.NMR 13C, 1H and IR studies show only one Z stereoisomer (no methylenic form) with a strong chelation between zinc and the carbonyl oxygen of the ester and solvated by only one solvent molecule.Hydrolysis can be achieved by two concurrent mechanisms with or without transposition.