17422-12-7

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-methyl-3-oxopentanoate is used as an intermediate in the synthesis of antiproliferative polyketide (+)-R-aureothin, which has potential applications in the development of anti-cancer drugs. Its role in the synthesis process is crucial for creating compounds with therapeutic properties.

InChI:InChI=1/C7H12O3/c1-4-6(8)5(2)7(9)10-3/h5H,4H2,1-3H3

Upstream product

• 554-12-1 propanoic acid methyl ester 
• 23426-63-3 2-bromo-2-methylpropionic acid methyl ester 
• 895167-75-6 2-(4-morpholinyl)-2-(N,N-bis(trimethylsilyl)aminothio)iminoacetonitrile 
• 30414-53-0 methyl propanoyl acetate 
• 74-88-4 methyl iodide 
• 108-12-3 isopentanoyl chloride 
• 67-56-1 methanol 
• 79-03-8 propionyl chloride 
• 60-29-7 diethyl ether 
• 5445-17-0 Methyl 2-bromopropionate 
• 71-43-2 benzene 
• 174534-00-0 1-(2'-methyl-3'-oxo)pentanoyl-3,5-dimethylpyrazole 

Downstream Products

• 116868-95-2 (+/-)-methyl 1,3-dimethyl-2-oxo-3-cyclohexene-1-carboxylate 
• 40790-56-5 2,6-dimethyl-2-cyclohexen-1-one 
• 187266-01-9 methyl (-)-(1R)-1,3-dimethyl-2-oxocyclohex-3-ene-1-carboxylate 
• 473236-96-3 2-ethyl-3-methyl-4-hydroxy-6,7-difluoroquinoline 
• 473236-97-4 2-ethyl-3-methyl-4-hydroxy-5,6-difluoroquinoline 
• 1352662-72-6 4-ethyl 1-methyl 3-(4-methoxyphenylamino)-2-methyl-2-propionylsuccinate 
• 1225789-07-0 1-(4-bromophenyl)-2-methylpentan-3-one 
• 6137-11-7 4-methyl-3-heptanone 
• 26118-97-8 2-allyl-3-pentanone 
• 23936-95-0 2-Methyl-1-phenylpentan-3-one 
• 17042-16-9 4-methyl-3-hexanone 
• 244027-76-7 methyl 6-benzyloxy-2,4-dimethyl-3,5-dioxohexanoate 
• 244024-64-4 6-(6-(benzyloxy)benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one 
• 96843-12-8 Thiolactone 

Relevant academic research and scientific papers

Antitubercular agents. Part 2: New thiolactomycin analogues active against Mycobacterium tuberculosis

Structurally modified analogues of naturally occurring antibiotic thiolactomycin, substituted at 4-position of the thiolactone ring have been prepared and evaluated for their antitubercular activity. Some of the compounds have exhibited potential activity against Mycobacterium tuberculosis.

Origins of stereoselectivity in the α-alkylation of chiral hydrazones

Density functional theory calculations and experiment reveal the origin of stereoselectivity in the deprotonation-alkylation of chiral N-amino cyclic carbamate (ACC) hydrazones. When the ACC is a rigid, camphor-derived carbamate, the two conformations of the azaenolate intermediate differ in energy due to conformational effects within the oxazolidinone ring and steric interactions between the ACC and the azaenolate. An electrophile adds selectively to the less-hindered π-face of the azaenolate. Although it was earlier reported that use of ACC auxiliaries led to α-alkylated ketones with er values of 82:18 to 98:2, B3LYP calculations predict higher stereoselectivity. Direct measurement of the dr of an alkylated hydrazone prior to removal of the auxiliary confirms this prediction; the removal of the auxiliary under the reported conditions can compromise the overall stereoselectivity of the process.

Convenient and efficient syntheses of β-keto esters and β-keto amides directly from α-alkylacetyl chlorides

The α-alkylacetyl chlorides were slowly treated with dried triethylamine, followed by treatment with alcohols or amines, to produce β-keto esters or β-keto amides, respectively. The process is a convenient alternative to prepare β-keto esters and β-keto amides.

Chemoenzymatic synthesis of (5S)- and (5R)-hydroxymethyl-3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one: a precursor of thiolactomycin and determination of its absolute configuration

A convenient enantioselective synthesis of (5S)- and (5R)-hydroxymethyl-3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one, a key intermediate in the synthesis of thiolactomycin has been carried out by a Carica papaya lipase-mediated resolution protocol to

Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones

The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.

On the regioselectivity and diastereoselectivity of ACC hydrazone alkylation

The asymmetric α-allylation of 3-pentanone using several different N-amino cyclic carbamate (ACC) auxiliaries is described. The level of asymmetric induction was found to range from er?=?93:7 to er?=?99:1. The factors that lead to compromised selectivity

Synthesis, antimalarial evaluation and molecular docking studies of some thiolactone derivatives

In present study novel thiolactone derivatives were designed, synthesized and characterized by various analytical techniques such as IR, 1H NMR, 13C NMR, mass spectral data and elemental analysis. All synthesized compounds were evaluated for in?vitro antimalarial activity against Dd2 and 3d7 strain of P.?falciparum. All synthesized compounds were also subjected for molecular docking study with pf KASI/II enzyme to analyze their binding orientation in the active site of the enzyme. Compounds 5d, 5e, and 5i found to be most potent with IC50 in the range of 0.09–0.19?μM and 0.03–0.04?μM against the Dd2 strain and 3D7 strain respectively as well as they showed good binding affinities with the residues of the active site of pf KASI/II.

Unexpected Direct Synthesis of N-Vinyl Amides through Vinyl Azide–Enolate [3+2] Cycloaddition

The unexpected synthesis of industrially important N-vinyl amides directly from aldehydes and α,β-unsaturated N-vinyl amides from esters is reported. This reaction probably proceeds through an initial [3+2] azide–enolate cycloaddition involving a vinyl azide generated in situ. A survey of the reaction scope and preliminary mechanistic findings supported by quantum computational analysis are reported, with implications for the future development of atom-efficient amide synthesis. Intriguingly, this study suggests that (cautious) reevaluation of azidoethene as a synthetic reagent may be warranted.

Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations

Abstract A flexible route to piperidine-2,4-diones variously substituted at the 6-, 5,6- and 2,6-positions, both with and without 1-substitution, is described; no N-protective group is required. A related regioselective Dieckmann cyclisation is also described that uses Davies' α-methylbenzylamine auxiliary and affords 6-substituted piperidine-2,4-diones enantioselectively.

Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases

α-Alkyl-β-hydroxy esters were obtained via dynamic kinetic resolution (DKR) employing purified or crude E. coli overexpressed alcohol dehydrogenases (ADHs). ADH-A from R. ruber, CPADH from C. parapsilosis and TesADH from T. ethanolicus afforded syn-(2R,3S) derivatives with very high selectivities for sterically not impeded ketones ('small-bulky' substrates), while ADHs from S. yanoikuyae (SyADH) and Ralstonia sp. (RasADH) could also accept bulkier keto esters ('bulky-bulky' substrates). SyADH also provided preferentially syn-(2R,3S) isomers and RasADH showed in some cases good selectivity towards the formation of anti-(2S,3S) derivatives. With anti-Prelog ADHs such as LBADH from L. brevis or LKADH from L. kefir, syn-(2S,3R) alcohols were obtained with high conversions and diastereomeric excess in some cases, especially with LBADH. Furthermore, due to the thermodynamically favoured reduction of these substrates, it was possible to employ just a minimal excess of 2-propanol to obtain the final products with quantitative conversions. Copyright