2046-21-1

Usage

Synthesis Reference(s)

Chemistry Letters, 11, p. 1607, 1982The Journal of Organic Chemistry, 48, p. 1133, 1983 DOI: 10.1021/jo00155a051Tetrahedron Letters, 14, p. 827, 1973

InChI:InChI=1/C8H14O3/c1-7(9)5-3-4-6-8(10)11-2/h3-6H2,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 110-83-8 cyclohexene 
• 67-56-1 methanol 
• 591-49-1 1-methylcyclohex-1-ene 
• 106-73-0 methyl heptanoate 
• 583-60-8 2-Methylcyclohexanone 
• 1686-22-2 vanadium(V) oxytriethoxide 

Downstream Products

• 102590-03-4 6,6-bis-(4-hydroxy-3,5-dimethyl-phenyl)-heptanoic acid 
• 227751-46-4 5-[1,8]-naphthyridin-2-yl-pentanoic acid methyl ester 
• 501-02-0 (-)-pinidine 
• 148372-19-4 (2R,6R)-1-<(benzyloxy)methoxy>-6-methylpiperidine-2-methanol 
• 148372-20-7 (2R,6R)-1-Benzyloxymethoxy-6-methyl-piperidine-2-carbaldehyde 
• 238432-36-5 toluene-4-sulfonic acid 5-(2-methyl-[1,3]dioxolan-2-yl)-pentyl ester 
• 36651-23-7 5-(2-methyl-[1,3]dioxolan-2-yl)-pentan-1-ol 
• 253309-50-1 7-(triphenylmethoxy)-2-heptanol 
• 227751-47-5 5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-pentanoic acid methyl ester 
• 55099-47-3 (+/-)-Ethyl 6-hydroxyheptanoate 
• 110663-28-0 6,6-bis-(4-hydroxy-3-methyl-phenyl)-heptanoic acid 

Relevant academic research and scientific papers

Iron-catalyzed oxidative functionalization of C(sp3)-H bonds under bromide-synergized mild conditions

An efficient oxidation and functionalization of C-H bonds with an inorganic-ligand supported iron catalyst and hydrogen peroxide to prepare the corresponding ketones was achieved using the bromide ion as a promoter. Preliminary mechanistic investigations indicated that the bromide ion can bind to FeMo6 to form a supramolecular species (FeMo6·2Br), which can effectively catalyze the reaction.

Combined effects on selectivity in Fe-catalyzed methylene oxidation

Methylene C-H bonds are among the most difficult chemical bonds to selectively functionalize because of their abundance in organic structures and inertness to most chemical reagents. Their selective oxidations in biosynthetic pathways underscore the power of such reactions for streamlining the synthesis of molecules with complex oxygenation patterns. We report that an iron catalyst can achieve methylene C-H bond oxidations in diverse natural-product settings with predictable and high chemo-, site-, and even diastereoselectivities. Electronic, steric, and stereoelectronic factors, which individually promote selectivity with this catalyst, are demonstrated to be powerful control elements when operating in combination in complex molecules. This small-molecule catalyst displays site selectivities complementary to those attained through enzymatic catalysis.

Reaction of 3,5-disubstituted 4,5-dihydroisoxazoles with hexacarbonylmolybdenum

Depending on the reaction conditions and structure of the 5-substituent, reactions of substituted 4,5-dihydroisoxazoles with hexacarbonylmolybdenum involve cleavage of the heteroring at the N-O bond, its aromatization, or/and 1,3-decyclization.

Oxidation of 2-alkylcycloalkanones with iodine-cerium(IV) salts in alcohols

The reaction of 2-alkylcycloalkanones with iodine-cerium(IV) salts in alcohols (methanol, ethanol, propan-1-ol or propan-2-ol) gave the respective oxo ester in 28-98% yields.

Oxovanadium(V)-Induced Ring-Opening Oxygenation of Cyclic Ketones in Alcohol

Cyclic ketones underwent ring-opening oxygenation on treatment with VO(OEt)Cl2 in alcohol under oxygen to give the corresponding keto ester or diesters depending on the substituent at 2-position.This system was applicable to a catalytic reaction.

Oxidative Cleavage of Olefins into Carboxylic Acids with Hydrogen Peroxide by Tungstic Acid

A facile conversion of olefins into carboxylic acids could be achieved by using aqueous hydrogen peroxide (35percent-H2O2) in the presence of catalytic amounts of tungstic acid (5 wtpercent).The oxidation was markedly influenced by the acidity of the reaction medium, and it was found to proceed favorably under a weak acidic condition (pH 4-5).

OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XVIII. INVESTIGATION OF A NEW OZONOLYTIC SYNTHESIS OF CARBOXYLIC ACIDS

By identification of the 18O isotope label in the oligomeric peroxide obtained by ozonization of a cyclic olefin in the presence of heavy oxygen and also in the product from catalytic isomerization of this peroxide ( the α,ο-dicarboxylic acids or its dimethyl ester ) it was shown that oxygen enters the ozonolysis product when the reaction is carried out in ether solvents.It is suggested that the increased content of active oxygen in the ozonolysis peroxy product is due to oxidation of the ether solvent to form α-hydroperoxide and addition of the latter to the oligomeric zwitterion, solvated by the polar solvents.It was established that the catalytic and thermal isomerization of the oligomeric peroxides and ozonides of cyclic olefins to the α,ο-dicarboxylic acids and ο-formyl carboxylic acids occurs through the oligomeric α-hydroxy peresters and α-hydroxy esters respectively.