2960-66-9

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL TRANS-4-OXO-2-BUTENOATE is used as an intermediate for the synthesis of pharmaceutically active molecules. Its role in the creation of these molecules is essential, as it can be transformed into various compounds with potential therapeutic properties.
Used in Asymmetric Catalytic Alkynylation:
In the field of organic chemistry, ETHYL TRANS-4-OXO-2-BUTENOATE is used in the asymmetric catalytic alkynylation of acetaldehyde. This process produces attractive synthons, which are versatile building blocks for the synthesis of complex organic molecules. One notable example of a compound synthesized using this method is (+)-Tetrahydropyrenophorol, a compound with potential applications in various industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 3421, 1984 DOI: 10.1021/jo00192a047Synthetic Communications, 18, p. 1913, 1988 DOI: 10.1080/00397918808068257Tetrahedron Letters, 31, p. 2145, 1990 DOI: 10.1016/0040-4039(90)80094-3

InChI:InChI=1/C6H8O3/c1-2-9-6(8)4-3-5-7/h3-5H,2H2,1H3/b4-3+

Upstream product

• 623-70-1 ethyl (E)-crotonate 
• 10544-63-5 ethyl crotonate 
• 10080-68-9 (E)-ethyl 4-hydroxybut-2-enoate 
• 1617-18-1 ethyl 3-butenoate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 5344-23-0 diethoxyacetaldehyde 
• 64-17-5 ethanol 
• 2396-84-1 (2E,4E)-ethyl hexa-2,4-dienoate 
• 36680-28-1 (Z)-3-(ethoxycarbonyl)propenoyl chloride 
• 49653-17-0 ethyl 2-ethoxyglycolate 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 110-00-9 furan 
• 60-29-7 diethyl ether 
• 7664-93-9 sulfuric acid 

Downstream Products

• 103441-29-8 (+/-)-trans-6-formyl-cyclohex-3-enecarboxylic acid ethyl ester 
• 95892-50-5 4-(2,4-dinitro-phenylhydrazono)-trans-crotonic acid ethyl ester 
• 74525-65-8 dodeca-2t,4c,11-trienal 
• 82667-57-0 (2E,4Z)-2,4,10-Dodecatrien-1-al 
• 345619-05-8 (2E,4E)-2,4,10-Dodecatrien-1-al 
• 82667-58-1 (2E,4E)-2,4,11-Dodecatrien-1-al 
• 82667-56-9 (2E,4Z)-2,4,9-Dodecatrien-1-al 
• 345619-07-0 (2E,4E)-2,4,9-Dodecatrien-1-al 
• 3025-30-7 ethyl (2E,4Z)-2,4-decadienoate 
• 7328-34-9 ethyl 2E,4E-decadienoate 
• 497161-72-5 (2S,4R)-2-Ethoxy-3,4-dihydro-2H-pyran-4-carboxylic acid ethyl ester 
• 497161-72-5 (2R,4R)-2-Ethoxy-3,4-dihydro-2H-pyran-4-carboxylic acid ethyl ester 
• 101820-69-3 imidazo[1,2-α]pyridin-3-yl-acetic acid ethyl ester 
• 709043-77-6 (E)-(4R,5S)-6-((S)-4-Benzyl-2-thioxo-thiazolidin-3-yl)-4-hydroxy-5-(2-methyl-[1,3]dithiolan-2-ylmethyl)-6-oxo-hex-2-enoic acid ethyl ester 

Relevant academic research and scientific papers

Fabrication and degradation of polyperoxides by a radical chain process under mild conditions

We have fabricated polyperoxides as new kinds of environment-friendly and degradable polymers using 1,3-diene compounds and oxygen as the starting comonomers under mild temperature and pressure conditions. They degrade in a radical chain mechanism by various stimuli; for example, degradation induced by physical (heating or irradiation), chemical (redox), and biochemical (enzymatic) stimuli.

Total synthesis of the lycopodium alkaloid serratezomine a using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin

Serratezomine A is a member of the structurally diverse class of compounds known as the Lycopodium alkaloids. The key supporting studies and successful total synthesis of serratezomine A are described in this account. Significant features of the synthesis include the first application of free radical mediated vinyl amination and Hwu's oxidative allylation in a total synthesis and an intramolecular lactonization via a transannular SNi reaction. Minimal use of protecting groups and the highly diastereoselective formation of a hindered, quaternary stereocenter using an umpolung allylation are also highlights from a strategy perspective. Observation of quaternary carbon epimerization via a retro-Mannich/Mannich sequence highlights the additional challenge presented by the axial alcohol at C8 in serratezomine A.

Ring-opening reactions of cyclopropanes. Part 8.1 Nitrosation of donor-acceptor cyclopropanes

The reaction of 2,2-dialkoxycyclopropane-1-carboxylates 1a-d and monoalkoxycyclopropane 1e with NOCl gives isoxazoline- and/or isoxazole-3-carboxylates by regioselective ring-opening at C1-C2 bond. A mechanistic interpretation suggests the intermediacy of well-stabilised dipolar species.

Diastereoselectivity in the epoxidation of γ-hydroxy α,β-unsaturated esters: Temperature and solvent effect

The diastereoselectivity in the nucleophilic epoxidation of γ-hydroxy α,β-unsaturated compounds using lithium-tert-butylperoxide is highly dependent on the reaction solvent but not influenced by the temperature. The free hydroxyl is key for stereoselection.

Bromination and iodination of donor-acceptor cyclopropanes. Evidence for an ET mechanism

Ethyl 2,2-dimethoxycyclopropanecarboxylates 1a-d react easily with Br2 and I2 in CCl4 or CH2Cl2 leading, in high yields, to 1-ethyl-4-methyl 2-halobutanedioates 2 and 3, respectively. Bromination in the presence of pyridine, NBS, trimethyl phosphate, and iodination with ICl and ICl/pyridine has been also performed. A common SET mechanism may be proposed for both halogenations; depending on the reaction conditions, bromination can also occur via acid-catalysed or SE2 routes. The reaction of the 2-ethoxyanalogues cis-12 and trans-12 with the same halogens proceeds in a similar manner, giving 3-formyl-2-haloesters along with the corresponding diethylacetals as main products. Iodination of 12 with the catalytic system NaI/m-CPBA/18-crown-6 has also been investigated.

The first example of a singlet oxygen induced double bond migration during sulfide photooxidation. Experimental evidence for sulfone formation via a hydroperoxy sulfonium ylide

The first example of the formation of a sulfone concomitant with double bond migration aunng photooxidation of a sulfide is reported. Evidence is presented which demonstrates that the double bond migration is not a result of a prior acid-catalyzed rearrangement of an unrearranged sulfone precursor. This unusual observation is used to argue that the sulfone is formed via rearrangement of a hydroperoxy sulfonium ylide intermediate.

Stereoselective synthesis of methyl and ethyl (2E,4Z)-2,4-decadienoates from (E)-4,4-dimethoxy-2-butenal

Methyl and ethyl (2E,4Z)-2,4-decadienoates were synthesized starting from (E)-4,4-dimethoxy-2-butenal.

Catalytic oxidation of furan and hydrofuran compounds. 5. Hydroxy- and ethoxydihydrofurans and ethoxyfuran - New products from the reaction of furan with hydrogen peroxide

It was established for the first time by chromato-mass spectrometry that 2-X-5-Y-2,5-dihydrofurans (X, Y = OH, OEt) and 2-ethoxyfuran are formed during the oxidation of furan by hydrogen peroxide in a mixture of water and ethanol in the presence of VOSO4. Stable tautomeric forms of 2-hydroxy- and 2,5-dihydroxyfurans - 2(5H)-furanone and 5-ethoxy-2(5H)-furanone respectively - were isolated from the reaction mixture. A probable scheme for the main reaction paths is proposed. 1999 Kluwer Academic/Plenum Publishers.

Catalytic asymmetric carbonyl-ene reactions with alkynylogous and vinylogous glyoxylates: Application to controlled synthesis of chiral isocarbacyclin analogues

The asymmetric carbonyl-ene reaction with alkynylogous and vinylogous glyoxylates (1, 2) catalyzed by a binaphthol-derived chiral titanium complex is described. The catalytic asymmetric ene reaction with aldehyde (1) can be applied to the double asymmetric synthesis of isocarbacyclin analogues bearing a 2-allenyl side chain.