2832-10-2

Usage

Uses

Used in Pharmaceutical Synthesis:
ETHYL 4-ACETYL-5-OXOHEXANOATE is used as a key intermediate in the synthesis of curcumin analogs with potential antiandrogenic activity. These analogs include [7-(4-hydroxy-3-methoxyphenyl)-4-[3-(4-hydroxy-3-methoxyphenyl)acryloyl]-5-oxohepta-4,6-dienoic acid ethyl ester] and [7-(4-hydroxy-3-methoxyphenyl)-4-[3-(4-hydroxy-3-methoxyphenyl)acryloyl]5-oxohepta-4,6-dienoic acid], which are being explored for their potential therapeutic effects in treating conditions related to androgen excess.
Used in Chemical Research:
In the field of chemical research, ETHYL 4-ACETYL-5-OXOHEXANOATE is utilized as a versatile building block for the development of novel compounds with diverse applications, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique chemical properties make it a valuable asset in the design and synthesis of complex molecular structures.

Synthesis Reference(s)

Synthesis, p. 1062, 1990 DOI: 10.1055/s-1990-27094

InChI:InChI=1/C10H16O4/c1-4-14-10(13)6-5-9(7(2)11)8(3)12/h11H,4-6H2,1-3H3/b9-7+

Upstream product

• 15435-71-9 sodium acetoacetonate 
• 623-71-2 ethyl 3-chloropropanoate 
• 123-54-6 acetylacetone 
• 140-88-5 ethyl acrylate 
• 1142402-23-0 ethyl 3-(1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptan-7-yl)-propanoate 

Downstream Products

• 54278-10-3 ethyl 5-(ethoxycarbonyl)-2,4-dimethyl-1H-pyrrole-3-propanoate 
• 98885-86-0 (4Z,6E)-5-Hydroxy-7-phenyl-4-[(E)-(3-phenyl-acryloyl)]-hepta-4,6-dienoic acid ethyl ester 
• 98886-22-7 (E)-5-Oxo-7-phenyl-4-[(E)-(3-phenyl-acryloyl)]-hept-6-enoic acid ethyl ester 
• 3128-06-1 5-ketohexanoic acid 
• 64-19-7 acetic acid 
• 666181-84-6 (E)-ethyl-7-(3,4-dimethoxyphenyl)-4-((E)-3-(3,4-dimethoxyphenyl)acryloyl)-5-oxohept-6-enoate 
• 54605-46-8 4-acetyl-5-oxohexanoic acid 
• 1082060-37-4 3'-(4-fluorophenyl)-4-[3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-propyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine hydrochloride 

Relevant academic research and scientific papers

Synthesis and tautomerism of curcumin derivatives and related compounds

1,7-Bis(4′-hydroxy-3′-trifluoromethoxyphenyl)-1,6-heptadiene-3,5-dione (2a), related to curcumin, and thirteen 4-substituted derivatives were prepared and their keto/enol ratio in DMSO[D6] was determined by 19F NMR because the enolic form of these related curcumins had been shown to bind to amyloid plaques in the Alzheimer brain. The parent compound and the 4-ethoxycarbonyl derivative were almost 100% in the enolic form that contains a conjugated hepta-1,4,6-trien-3-on-5-ol backbone. Enolisation decreased to varying amounts in the derivatives that had 4-substituted alkyl groups. Attempts to prepare the 4-hydroxypropyl derivative by hydrolysis of O-methoxymethyl 2m or O-tetrahydropyranyloxy 2n protected derivatives led to cyclised products. A related pyrimidine compound 6b that mimicked a fixed enol form was also prepared.

ONE-STEP, FAST, 18F-19F ISOTOPIC EXCHANGE RADIOLABELING OF DIFLUORO-DIOXABORININS AND USE OF SUCH COMPOUNDS IN TREATMENT

A compound according to Formula (I) or a pharmaceutically acceptable salt and/or solvate thereof, wherein X1 and X2 are each independently 18F or 19F; R1 and R2 are each independently alkyl, amine, perfluoroalkyl, alkenyl, alkynyl, aryl, or aralkenyl; and R3 is H, halo, alkyl, alkyl ester, alkenyl, alkynyl, aryl, or aralkenyl; or wherein: R1 and R3 or R2 and R3 join to form a 6-membered cycloalkyl or heterocyclyl; or R1 and R3, R2 and R3, or R1, R2, and R3 join to form a substituted or unsubstituted polycyclic ring, wherein the polycyclic ring comprises fused cycloalkyl, heterocycloalkyl, aryl, or heteroaryl rings.

Chemiluminescence in decomposition of bridged 1,2,4,5-tetraoxanes catalyzed by ferrocene

Chemiluminescence was observed in ferrocene-catalyzed decomposition of bridged 1,2,4,5-tetraoxanes, namely, 2,3,5,6-tetraoxabicyclo[2.2.1]heptanes. The chemi- and photoluminescence spectra revealed the main products and luminescence emitters to be β-diket

Direct imine acylation for molecular diversity in heterocyclic synthesis

Imines and carboxylic acids have been directly coupled using propylphosphonic acid anhydride and NEt(i-Pr)2 to give N-acyliminium ions, which were intramolecularly trapped with oxygen, nitrogen, sulfur, and carbon nucleophiles to provide a wide range of structurally diverse heterocycles.

An efficient route to dipyrrinones: Synthesis of xanthobilirubic acid methyl ester

Structurally interesting and complicated dipyrrinones, such as xanthobilirubic acid methyl ester (9), can be synthesized on a large scale from simple, inexpensive starting materials like ethyl acetoacetate, 2,4-pentanedione (1) and ethyl acrylate in 8 steps with an average yield of 80% at each step and an overall 17% yield.

ALKYLATION OF CH ACIDS IN THE PRESENCE OF POTASSIUM CARBONATE. IV. ALKYLATION OF 2,4-PENTANEDIONE AND 3-METHYL-2,4-PENTANEDIONE

The reaction of 2,4-pentanedione and 3-methyl-2,4-pentanedione with ethyl acrylate in the presence of potassium carbonate gave the Michael adducts.The acylotropic rearrangement of the products from the reaction of 3-methyl-2,4-pentanedione with ethyl α-bromoacrylate and dibromoethane under the influence of potassium carbonate was investigated.

Xanthobilirubic Acid and Its Amides. Synthesis, Spectroscopy, and Solution Structures

Xanthobilirubic acid, 5--2,4-dimethyl-1H-pyrrol-3-propanoic acid, its methyl ester, amide, N-methylamide and dimethylamide, and kryptopyrromethenone have been synthesized and characterized spectroscopically.In d6-DMSO solution all pyrromethenones were monomeric, with lactam and pyrrole N-Hs H-bonded to solvent.In deuteriochloroform, the pyrromethenones preferred a dimeric form, with intramolecular H-bonding between the lactam C=O of one unit and the lactam and pyrrole N-Hs of the second.

Nickel-Catalyzed Michael Additions of β-Dicarbonyls

Bis(2,4-pentanedionato)nickel(II) is found to be a mild, efficient, and simple to use catalyst for the Michael additions of β-dicarbonyls.Yields are higher than with traditional strongly basic catalysts, unwanted side reactions are reduced, and workup procedures are greatly simplified.The reactions appear to be quite general as β-diketones, β-keto esters, β-keto amides, and β-diesters are all found to react.A rational mechanism which suggests further research is presented.