37160-77-3

Usage

InChI:InChI=1/C8H16O2/c1-3-4-5-6-8(10)7(2)9/h8,10H,3-6H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 818-72-4 1-Octyn-3-ol 
• 20653-90-1 (+/-)-2,3-octanediol 
• 24251-77-2 3-chloro-octan-2-one 
• 82215-74-5 2-diethylaminopropionitrile 
• 66-25-1 hexanal 
• 127-17-3 2-oxo-propionic acid 
• 111-13-7 hexyl-methyl-ketone 
• 57-60-3 piruvate 
• 57648-55-2 (E)-oct-3-en-2-ol 
• 3391-86-4 1-octen-3-ol 
• 415900-45-7 tert-butyl 2-acetoxy-2-acetylheptanoate 
• 36959-98-5 acetic acid 1-acetyl-hexyl ester 
• 113-24-6 sodium pyruvate 

Downstream Products

• 152519-33-0 (S)-2-hydroxyhexan-⁽³⁾-one 
• 84435-13-2 (+)-(2S)-2-hydroxyoctan-3-one 
• 585-25-1 octane-2,3-dione 

Relevant academic research and scientific papers

Thermodynamic favorable CO2 conversion via vicinal diols and propargylic alcohols: A metal-free catalytic method

Organocatalysis represents a promising field in chemical fixation of CO2. Herein, a facile metal-free strategy was reported for the one-pot preparation of cyclic carbonates and α-hydroxy ketones from vicinal diols, propargylic alcohols and CO2. Wide scope of vicinal diols and propargylic alcohols was demonstrated to be efficient under the DBU-catalyzed conditions. A plausible mechanism was proposed, which included detailed main and side reactions under the metal-free conditions.

The gold-catalyzed formal hydration, decarboxylation, and [4+2] cycloaddition of alkyne derivatives featuring L2/Z-type diphosphinoborane ligands

The catalytic formal hydration of alkynes and decarbox-ylation of alkynoic acid were developed using a Au catalyst featuring a Z-ligand. Furthermore, the intramolecular [4+2] cycloaddition of the alkynoic acid-alkene derivative for the formation of the oxabicyclo[4.4.0] skeleton also proceeded.

Selective Synthesis of Unsymmetrical Aliphatic Acyloins through Oxidation of Iridium Enolates

The first method to access unsymmetrical aliphatic acyloins is presented. The method relies on a fast 1,3-hydride shift mediated by an IrIII complex in allylic alcohols followed by oxidation with TEMPO+. The direct conversion of allylic alcohols into acyloins is achieved in a one-pot procedure. Further functionalization of the Cα′ of the α-amino-oxylated ketone products gives access to highly functionalized unsymmetrical aliphatic ketones, which further highlights the utility of this transformation.

Synthesis and Characterization of Urofuranoic Acids: In Vivo Metabolism of 2-(2-Carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic Acid (CMPF) and Effects on in Vitro Insulin Secretion

CMPF (2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid) is a metabolite that circulates at high concentrations in type 2 and gestational diabetes patients. Further, human clinical studies suggest it might have a causal role in these diseases. CMPF inhibits insulin secretion in mouse and human islets in vitro and in vivo in rodents. However, the metabolic fate of CMPF and the relationship of structure to effects on insulin secretion have not been significantly studied. The syntheses of CMPF and analogues are described. These include isotopically labeled molecules. Study of these materials in vivo has led to the first observation of a metabolite of CMPF. In addition, a wide range of CMPF analogues have been prepared and characterized in insulin secretion assays using both mouse and human islets. Several molecules that influence insulin secretion in vitro were identified. The molecules described should serve as interesting probes to further study the biology of CMPF.

Α - hydroxy ketone compound low priced high-efficient synthetic method

The invention discloses a cheap and efficient synthesis method of an alpha-hydroxyketone compound. The synthesis method is characterized in that a carbonyl compound undergoes an oxidation hydroxylation reaction at 10-120DEG C under normal pressure with iodine simple substance, N-bromosuccimide, copper bromide, bromine simple substance, hydrogen bromide, N-iodosuccimide or hydrogen iodide as a catalyst, sulfoxide as an oxidant, water or sulfoxide as a hydroxy source and sulfoxide, ethyl acetate, N,N-dimethyl formamide, acetonitrile, toluene, 1,4-dioxane, 1,2-dichloroethane, tetrahydrofuran or H2O as a solvent, and converts into the alpha-hydroxyketone compound in a high selectivity manner. Compared with traditional synthesis methods, the method disclosed in the invention has the advantages of simple operation, high yield, simple conditions, easy purification, small waste discharge amount, simple reaction apparatus, and easy industrial production. The method has wide applicability and can be used for synthesizing various alpha-hydroxyketone compounds.

I2- or NBS-catalyzed highly efficient α-hydroxylation of ketones with dimethyl sulfoxide

An efficient method for the direct preparation of high synthetic valuable α-hydroxycarbonyls is described. The simple and readily available I2 or NBS was used as catalyst. DMSO acts as the oxidant, oxygen source, and solvent. A diverse range of tertiary Csp3-H bonds as well as more challenging secondary Csp3-H bonds could be hydroxylated in this transformation. The reaction is mild, less toxic and easy to perform.

Palladium-catalyzed selective anti-markovnikov oxidation of allylic esters

An aldol alternative: The palladium(II)-catalyzed anti-Markovnikov oxidation of allylic esters to aldehydes at room temperature provides a viable alternative to valuable cross aldol products. High regioselectivity towards the aldehyde product was achieved using the ester protecting group for the allylic alcohol. Rapid isomerization and the much higher rate of oxidation of the branched isomer result in the same product forming from both linear and branched allylic esters. Copyright

Revealing substrate promiscuity of 1-deoxy-D-xylulose 5-phosphate synthase

A study of DXP synthase has revealed flexibility In the acceptor substrate binding pocket for nonpolar substrates and has uncovered new details of the catalytic mechanism to show that pyruvate can act as both donor and acceptor substrate.

Isolable gold(I) complexes having one low-coordinating ligand as catalysts for the selective hydration of substituted alkynes at room temperature without acidic promoters

Hydration of a wide range of alkynes to the corresponding ketones has been afforded in high yields at room temperature by using gold(I)-phosphine complexes as catalyst, with no acidic cocatalysts required. Suitable substrates covering alkyl and aryl terminal alkynes, enynes, internal alkynes, and propargylic alcohols, including enantiopure forms, are cleanly transformed to the corresponding ketones in nearly quantitative yields. Acid-labile groups present in the substrates are preserved. The catalytic activity strongly depends on both the nature of the phosphine coordinated to the gold (I) center and the softness of the counteranion, the complex AuSPhOsNTf2 showing the better activity. A plausible mechanism for the hydration of alkynes through ketal intermediates is proposed on the basis of kinetic studies. The described catalytic system should provide an efficient alternative to mercury-based methodologies and be useful in synthetic programs.

A new route to protected acyloins and their enzymatic resolution with lipases

A series of 16 different 3-acyloxy methyl ketones, the acyloin acetates and butyrates (±)-5, was synthesised by a straight-forward new method through alkylation of tert-butyl 2-acyloxyacetoacetates 3, followed by chemoselective dealkoxy-carbonylation of the tert-butyloxycarbonyl group in the presence of other ester groups. Subsequent hydrolysis of (±)-5 can be achieved with base to give racemic acyloins 6, or with lipase catalysis to afford the corresponding non-racemic acyloins (S)-6. The remaining (R)-acyloin esters 5 can be racemised and resubjected to the procedure, or hydrolysed chemically. The kinetic resolution with two of the six tested enzymes, CAL-B and BCL (PS) lipase, proceeded selectively [enantiomeric ratio (E) values between 50 and > 200] and most of the acyloins (S)-6 were obtained in very high enantiomeric excesses (up to > 99% ee). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.