100330-50-5

Usage

Uses

Used in Flavor and Fragrance Industry:
Methyl 3-oxohept-6-ynoate is utilized as a flavoring and fragrance ingredient due to its distinctive fruity scent, enhancing the sensory experience in various consumer products.
Used in Pharmaceutical Development:
In the pharmaceutical industry, methyl 3-oxohept-6-ynoate is employed as a potential candidate for the development of drugs to treat Alzheimer's disease, capitalizing on its ability to inhibit the acetylcholinesterase enzyme, which is implicated in the progression of the disease.
Used as a Chemical Intermediate:
Methyl 3-oxohept-6-ynoate serves as an intermediate in the synthesis of various pharmaceuticals and organic compounds, facilitating the creation of a wide range of products across different industries.

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 106-96-7 propargyl bromide 
• 6089-09-4 4-pentynoic acid 
• 38330-80-2 monomethyl monopotassium malonate 
• 30414-53-0 methyl propanoyl acetate 
• 113647-42-0 3-Bromo-but-1-yne 
• 67-56-1 methanol 

Downstream Products

• 191329-60-9 [5-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-dihydro-furan-(2E)-ylidene]-acetic acid methyl ester 
• 646038-17-7 (S)-3-oxo-2-(3-oxocyclohexyl)hept-6-ynoic acid methyl ester 
• 646038-22-4 (S)-3-oxo-2-(3-oxocycloheptyl)hept-6-ynoic acid methyl ester 
• 23260-43-7 2-(methoxycarbonyl)-3-methyl-2-cyclopenten-1-one 
• 1396312-81-4 8-but-3-ynyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-10-one 
• 1396312-89-2 benzyl (S,S)-1-(1-methyl-2-{4-[2-(10-oxo-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-azabenzo[de]anthracen-8-yl)ethyl]-1,2,3-triazol-1-yl}ethylcarbamoyl)-2-phenylethylcarbamate 

Relevant academic research and scientific papers

Gallium(III)- and calcium(II)-catalyzed Meyer-Schuster rearrangements followed by intramolecular aldol condensation or endo-Michael addition

The first gallium- and calcium-catalyzed Meyer-Schuster rearrangements are described. Under substrate control, the incipient conjugated ketones can be trapped intramolecularly by β-keto esters or amides to yield cyclic products after aldol condensation or endo-Michael addition. An interesting additive effect that promotes the latter tandem process with calcium has been found.

Calcium-Catalyzed Synthesis of Polysubstituted 2-Alkenylfurans from β-Keto Esters Tethered to Propargyl Alcohols

An efficient synthesis of polysubstituted 2-alkenylfurans using Ca(NTf2)2/KPF6as a catalytic mixture is described. It is based on the cycloelimination of readily available propargyl alcohols tethered to β-keto esters under dry conditions to avoid competitive Meyer–Schuster rearrangement. The furan can be further functionalized in situ by a calcium-catalyzed Friedel–Crafts-type reaction with secondary and tertiary alcohols. The title reaction allows for the high-yielding preparation of di-, tri-, and tetrasubstituted 2-alkenylfurans, which are important subunits of bioactive compounds.

Ring-Enlarging Annulatons. A One-Step Conversion of Cyclic Silyl Acyloins and ω-Alkynyl Acetals to Polycyclic Enediones

A new sequence of cationic reactions that converts cyclic silyl acyloins and ω-alkynyl acetals to polycyclic enediones is reported.For example, treatment of bis-1,2-((trimethylsilyl)oxy)cyclobutene and 2-(ethylenedioxy)-5-heptyne with excess boron trifluoride etherate in methylene chloride for 2 days provides 4-acetyl-3,5,6,6a-tetrahydro-6a-methyl-1-(2H)-pentalenone in 58percent yield.This product is formed via a sequence involving a Mukaiyama aldol reaction, a pinacol ring expansion, and a 5-exo-dig alkynyl ketone cyclization.In the case of terminal alkynes, the last cyclization occurs in a 6-endo-dig fashion.The scope and limitations of this process are studied, and a number of bi- and tricyclic ring systems are formed.

Synthesis of carbazoles based on gold-copper tandem catalysis

An efficient synthetic method for carbazoles has been developed employing diazo anilinoalkynes as substrates. Sequential activation of the orthogonal functional groups embedded in diazo anilinoalkyne substrates by tandem gold-copper catalysis leads to the formation of highly substituted carbazoles. Substrate scope reveals a broad tolerability toward the substitution on aryl groups.

COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH NLRP ACTIVITY

In one aspect, compounds of Formula AA, or a pharmaceutically acceptable salt thereof, are featured.The variables shown in Formula AA are as defined in the claims. The compounds of formula AA are NLRP3 activity modulators and, as such, can be used in the treatment of metabolic disorders (e.g. Type 2 diabetes, atherosclerosis, obesity or gout), a disease of the central nervous system (e.g. Alzheimer's disease, multiple sclerosis, Amyotrophic Lateral Sclerosis or Parkinson's disease), lung disease (e.g. asthma, COPD or pulmonary idiopathic fibrosis), liver disease (e.g. NASH syndrome, viral hepatitis or cirrhosis), pancreatic disease (e.g. acute pancreatitis or chronic pancreatitis), kidney disease (e.g. acute kidney injury or chronic kidney injury), intestinal disease (e.g. Crohn's disease or Ulcerative Colitis), skin disease (e.g. psoriasis), musculoskeletal disease (e.g. scleroderma), a vessel disorder (e.g. giant cell arteritis), a disorder of the bones (e.g. osteoarthritis, osteoporosis or osteopetrosis disorders), eye disease (e.g. glaucoma or macular degeneration), a disease caused by viral infection (e.g. HIV or AIDS), an autoimmune disease (e.g. Rheumatoid Arthritis, Systemic Lupus Erythematosus or Autoimmune Thyroiditis), cancer or aging.

Fluorescence labeling of amino acids and peptides with 7-aminocoumarins

Pechmann condensation is a straightforward protocol for the synthesis of alkynyl- and azido-substituted 7-(dialkylamino)coumarins, which can be coupled to amino acid and peptide derivatives by copper-catalyzed [3+2]-cycloaddition (click reaction) in high yield. This allows the introduction of these efficient fluorescence labels into biologically relevant molecules. Georg Thieme Verlag Stuttgart ? New York.

Copper/silver-cocatalyzed conia-ene reaction of linear β-alkynic β-ketoesters

A novel and general copper/silver catalytic system has been developed for the Conia-ene intramolecular reaction of linear β-alkynic β-ketoesters. In the presence of (CuOTf)2·C 6H6 and AgSbF6 (or AgOAc), a variety of the linear β-alkynic β-ketoesters selectively underwent the Conia-ene intramolecular reaction in moderate to good yields.

Synthesis of 2,5-disubstituted furans via palladium-catalyzed annulation of alkyl 3-oxo-6-heptynoates

The reaction of the readily available alkyl 3-oxo-6-heptynoates with aryl halides in the presence of K2CO3 and catalytic amounts of Pd(PPh3)4 at 100 °C provides a valuable new route to 2,5-disubstituted furans 3. Most probably, the furan ring is generated through an annulation reaction promoted by δ-arylpalladium complexes generated in situ and involving the nucleophilic attack of the ketonic oxygen across the carbon-carbon triple bond coordinated to palladium, followed by the base-catalyzed isomerization of the resultant stereoisomeric 2,5-dialkylidenetetrahydrofuran intermediates 4 and 5. The reaction is highly chemoselective. No evidence was obtained of carboannulation products. The reaction temperature has proven to be crucial for the success of the methodology. The K2CO3:alkyne ratio also affects the reaction outcome. The highest yields of furan derivatives have been obtained with aryl halides containing electron-withdrawing substituents, very likely because the higher acidity of the methylene protons of 4 and 5 favors the isomerization step. Extension of the methodology to methyl 3-oxo-7- substituted-6-heptynoates leads to the formation of 2,5-disubstituted furans containing a branched side chain. The presence of an alkyl substituent on the C-2 of the staring alkyne, however, seems to prevent the isomerization step. Treatment of ethyl 2-methyl-3-oxo-6-heptynoate under our standard conditions produced in fact the 2,5-dialkylidene derivative 5p in 42% yield, and no evidence of the corresponding furan derivative was attained.

New cobalt-catalyzed cycloisomerization of ε-acetylenic β-keto esters. Application to a powerful cyclization reactions cascade

The full details of investigations into the cobalt(I)-catalyzed ene type reaction of ε-acetylenic β-keto esters to form highly functionalized methylenecyelopentanes are described. The observed regio-, chemo-, and stereoselectivities support a process of cycloisomerization which controls the relative stereochemistry of two contiguous stereogenic centers. An efficient route to the basic skeleton of the phyllocladane family has been achieved via a one-pot sequence of cyclizations: ene type, [2 + 2 + 2], [4 + 2]. This new cascade created six carbon-carbon bonds and four rings in a totally stereoselective manner from an easily accessible acyclic polyunsaturated precursor.