5579-73-7

Usage

InChI:InChI=1/C10H18O2/c1-3-5-7-9(11)10(12)8-6-4-2/h3-8H2,1-2H3

Upstream product

• 1942-46-7 5-decyne 
• 2165-61-9 trans-2,3-dibutyloxirane 
• 109-72-8 n-butyllithium 
• 201230-82-2 carbon monoxide 
• 108-94-1 cyclohexanone 
• 591-51-5 phenyllithium 
• 156909-31-8 1,4-Didecylpiperazine-2,3-dione 
• 59417-06-0 1,4-dimethyl-2,3-dioxopiperazine 
• 6540-98-3 6-hydroxydecan-5-one 
• 56-23-5 tetrachloromethane 
• 10028-15-6 ozone 
• 64-19-7 acetic acid 
• 84298-28-2 1H-1,2,3-benzotriazol-1-yl(n-butyl)methanone 
• 7433-56-9 (E)-5-decene 

Downstream Products

• 109-52-4 valeric acid 

Relevant academic research and scientific papers

Requirements for mammalian carboxylesterase inhibition by substituted ethane-1,2-diones

Carboxylesterases (CE) are ubiquitous enzymes found in both human and animal tissues and are responsible for the metabolism of xenobiotics. This includes numerous natural products, as well as a many clinically used drugs. Hence, the activity of these agents is likely dependent upon the levels and location of CE expression. We have recently identified benzil is a potent inhibitor of mammalian CEs, and in this study, we have assessed the ability of analogues of this compound to inhibit these enzymes. Three different classes of molecules were assayed: One containing different atoms vicinal to the carbonyl carbon atom and the benzene ring [PhXC(O)C(O)XPh, where X = CH2, CHBr, N, S, or O]; a second containing a panel of alkyl 1,2-diones demonstrating increasing alkyl chain length; and a third consisting of a series of 1-phenyl-2-alkyl-1,2-diones. In general, with the former series of molecules, heteroatoms resulted in either loss of inhibitory potency (when X = N), or conversion of the compounds into substrates for the enzymes (when X = S or O). However, the inclusion of a brominated methylene atom resulted in potent CE inhibition. Subsequent analysis with the alkyl diones [RC(O)C(O)R, where R ranged from CH3 to C8H17] and 1-phenyl-2-alkyl-1,2-diones [PhC(O)C(O)R where R ranged from CH3 to C6H13], demonstrated that the potency of enzyme inhibition directly correlated with the hydrophobicity (c log P) of the molecules. We conclude from these studies that that the inhibitory power of these 1,2-dione derivatives depends primarily upon the hydrophobicity of the R group, but also on the electrophilicity of the carbonyl group.

Ruthenium-catalyzed alkyne oxidation with part-per-million catalyst loadings

Using a catalytic system of the (cymene)ruthenium dichloride dimer, [Ru(cymene)Cl2]2, (0.001 mol%) and iodine (10 mol%), a variety of alkynes bearing different functional groups were oxidized with tert-butyl hydroperoxide (TBHP; 70% solution in water) under mild conditions to give 1,2diketones in good to excellent yields. Two noteworthy features of the method are the extremely high catalyst productivity (TON up to 420,000) and scale-up to 1 mol. Preliminary mechanism investigations showed that iodonium ion and water were involved in the transformation.

Samarium diiodide promoted formation of 1,2-diketones and 1-acylamido-2-substituted benzimidazoles from N-acylbenzotriazoles

N-Acylbenzotriazoles, when treated with samarium diiodide in THF, undergo self-coupling reaction to afford 1,2-diketones in good to excellent yields; while when treated with samarium diiodide in CH3CN, they undergo ring-opening reaction to afford 1-acylamido-2-alkyl (or aryl) benzimidazoles in reasonable to good yields. A plausible mechanism was suggested.

Formation of 1,2-diketones by samarium diiodide promoted reaction of N-acylbenzotriazoles

Transformation of N-acylbenzotriazoles 1 into 1,2-diketones 2 in good to excellent yields has been realized by the use of samarium diiodide at room temperature.

Difluoroboroxymolybdenum fischer carbene complexes as precursors of acyl radicals: Dimerization and trapping with electron-deficient alkenes

Pentacarbonyl acyl molybdates 1 react with boron trifluoride to give difluoroboroxy Fischer carbene complexes 2, which undergo loss of the metal fragment at room temperature to form 1,2-diketones 3, 1,2-hydroxy ketones 4, or dimers 5 through a dimerization or decarbonylation-dimerization process of acyl radicals. Decomposition of 2 in the presence of electron-deficient alkenes 11 and 18 furnishes the two-, three-, and four-component coupling products 12, 13, 19, 20, and 21.

Synthesis of Symmetrically and Unsymmetrically Substituted α-Diones from Organometallic Reagents and 1,4-Dialkylpiperazine-2,3-diones

The reaction of an equimolar mixture of N,N'-dialkylethylenediamines and diethyl oxalate in diethyl ether or 2-propanol leads to 1,4-dialkylpiperazine-2,3-diones.As cyclic and nearly planar tetraalkyl oxamides, these compounds are able to react with 2 equiv of organolithium or Grignard compounds to form, after hydrolysis, symmetrically substituted α-diones in excellent yields.The sequential addition of 1 equiv each ot two different organolithium compounds affords unsymmetrically substituted α-diones when the more soluble longer chain dialkyl derivatives of piperazine-2,3-dione are employed.The dialkylethylenediamines can conveniently be recovered and recycled to the 1,4-dialkylpiperazine -2,3-diones in good yields.

Bi(III)-mandelate/DMSO : A New Oxidizing System for the Catalyzed C-C Cleavage of Epoxides

Bi(III)-mandelate was found to be an effective catalyst for the oxidative C-C bond cleavage of epoxides and their transformation into carboxylic acids in anhydrous DMSO medium.

A simple synthesis of symmetrical α-diones from organometallic reagents and 1,4-dimethyl-piperazine-2,3-dione

Short reflux of an equimolar mixture of N-N′-dimethyl ethylenediamine and diethyl oxalate in ipropanol or diethyl ether leads to 1,4-dimethyl-piperazine-2,3-dione, which is able to react with two equivalent of organolithium or Grignard compounds to form symmetrically substituted α-diones in excellent yields.

Synthesis of α-Hydroxy Ketones by Direct, Low-Temperature, in Situ Nucleophilic Acylation of Aldehydes and Ketones by Acyllithium Reagents

The reaction of n-, sec-, and tert-butyllithium with CO at atmospheric pressure at -110 and -135 deg C in the appropriate solvent system in the presence of ketones and aldehydes generates the acyllithium, RC(O)Li, which reacts with the carbonyl compound to give the α-hydroxy ketone, generally in good yield.Reactions with aldehydes are limited in scope, working well with the t-BuLi-derived acyllithium reagents, but not with n-BuC(O)Li.