14886-54-5

Basic information

• Product Name: methyl 4-oxo-4-cyclohexylbutanoate
• Synonyms: methyl 4-oxo-4-cyclohexylbutanoate
• CAS NO: 14886-54-5
• Molecular Weight: 198.262
• Mol File: 14886-54-5.mol

Chemical Properties

• CAS DataBase Reference: methyl 4-oxo-4-cyclohexylbutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-oxo-4-cyclohexylbutanoate(14886-54-5)
• EPA Substance Registry System: methyl 4-oxo-4-cyclohexylbutanoate(14886-54-5)

Safety Data

• Hazardous Substances Data: 14886-54-5(Hazardous Substances Data)

Upstream product

• 16076-59-8 γ--γ-ketobuttersaeure-methylester 
• 201230-82-2 carbon monoxide 
• 626-62-0 Cyclohexyl iodide 
• 292638-85-8 acrylic acid methyl ester 
• 931-50-0 cyclohexylmagnesium bromide 
• 1490-25-1 succinic acid monomethylester chloride 
• 15971-95-6 4-cyclohexyl-4-oxo-butyric acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 516472-44-9 methyl (E)-4-cyclohexyl-4-hydroxybut-2-enoate 
• 7327-99-3 4-oxo-but-2-enoic acid methyl ester 
• 168051-58-9 methyl 4-hydroxy-4-cyclohexyl-but-2-ynoate 
• 931-51-1 cyclohexylmagnesiumchloride 
• 23684-13-1 4-oxo-hex-5-enoic acid methyl ester 

Downstream Products

• 15971-95-6 4-cyclohexyl-4-oxo-butyric acid 
• 18930-19-3 1-cyclohexylbutane-1,4-diol 

Relevant articles and documents

Photoredox-Catalyzed Isomerization of Highly Substituted Allylic Alcohols by C?H Bond Activation

Photoredox-catalyzed isomerization of γ-carbonyl-substituted allylic alcohols to their corresponding carbonyl compounds was achieved for the first time by C?H bond activation. This catalytic redox-neutral process resulted in the synthesis of 1,4-dicarbonyl compounds. Notably, allylic alcohols bearing tetrasubstituted olefins can also be transformed into their corresponding carbonyl compounds. Density functional theory calculations show that the carbonyl group at the γ-position of allylic alcohols are beneficial to the formation of their corresponding allylic alcohol radicals with high vertical electron affinity, which contributes to the completion of the photoredox catalytic cycle.

Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters

This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate from the easily accessible γ-hydroxy-α,β-alkenoic ester. The in situ generated dienolate can react with benzaldehyde and undergo a practical, useful tandem allylic isomerization-Aldol reaction to afford more functionalized compounds.

Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes

Cyanoborohydrides are efficient reagents in the reductive addition reactions of alkyl iodides and electron-deficient olefins. In contrast to using tin reagents, the reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine or carbon-chlorine bond. The reaction system was successfully applied to three-component reactions, including radical carbonylation. The rate constant for the hydrogen abstraction of a primary alkyl radical from tetrabutylammonium cyanoborohydride was estimated to be 4 M-1 s-1 at 25 °C by a kinetic competition method. This value is 3 orders of magnitude smaller than that of tributyltin hydride.

Gold-catalysed cyclic ether formation from diols

Gold(I) and (III) salts have been found to be highly effective at the catalysis of ether formation from alcohols. Intramolecular ether formation of a 1,5-diol was also achieved, with a stereoselectivity that indicates that an SN1 mechanism predominates. In an attempt to form a seven-membered ring, a stable 14-membered dimer product was also formed. Attempts to control the diastereoselectivity of the reaction using a chiral anionic counterion did not give products with a high de.

Tin-free giese reaction and the related radical carbonylation using Alkyl iodides and cyanoborohydrides

Tin-free Giese reaction and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. The reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine and carbon-chlorine bonds. The iodine atom transfer followed by hydride reduction of the resulting carbon-iodine bond is proposed as a possible mechanism.

THERAPEUTIC AGENT FOR DIABETES

A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4and R5are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6is a hydrogen atom or an amino-protecting group; R1is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.

A general and straightforward approach to α,ω-ketoesters

Chemoselective cross-coupling reactions of monoesters of dicarboxylic acid chlorides with organocopper reagents derived from Grignard reagents, cuprous bromide, and lithium bromide, provide a simple and straightforward method for synthesizing a variety of ketoesters.

Process for producing 3,4-dihydrocoumarin derivatives

A process for producing a 3,4-dihydrocoumarin compound represented by formula (II): STR1 wherein R1 to R4 are as defined in the specification, comprising the steps of: (1) heating a 3-(2-cyclohexanoyl)propionic acid ester compound represented by formula (I): STR2 wherein R1 R5 are as defined in the specification, in the presence of at least one solid metal catalyst, thereby to allow said compound of formula (I) to undergo ring formation and dehydrogenation to yield said 3,4-dihydrocoumarin compound of formula (II) and, as a by-product, a coumarin compound represented by formula (III): STR3 wherein R1 to R4 are as defined above; (2) adding a catalyst which is as defined above to said reaction mixture, or bringing said reaction mixture into contact with oxygen to activate said catalyst used in said ring formation and dehydrogenation, without separating said coumarin compound from the reaction mixture that has undergone said ring formation and dehydrogenation; and (3) partially hydrogenating said by-product coumarin compound in said reaction mixture with hydrogen so as to convert said coumarin compound to a 3,4-dihydrocoumarin compound.

Double Alkylation of Carbon Monoxide via Free Radicals: Synthesis of Unsymmetrical Ketones

A novel method for the synthesis of unsymmetrical ketones via the free radical carbonylation of alkyl halides is described.The mechanism of the reaction involves the trapping of an alkyl free radical by CO, the addition of the acyl free radical so formed to an alkene, and termination of the reaction by the abstraction of a hydrogen atom from tributyltin hydride by the product acyl-substituted free radical.