601-79-6

Usage

Uses

Used in Pharmaceutical Industry:
Isopropylmalonic acid is used as an intermediate in the synthesis of various pharmaceuticals for its ability to form a wide range of derivatives with different properties and applications. Its role in creating bioactive compounds, such as antibiotics and anti-inflammatory drugs, underscores its importance in developing new medications and therapies.
Used in Agrochemical Industry:
Isopropylmalonic acid is utilized as a key component in the production of agrochemicals, contributing to the development of effective and innovative products for agricultural applications.
Used in Organic Synthesis:
As a starting material for the synthesis of complex molecules, isopropylmalonic acid is employed in organic synthesis to create a variety of chemical entities with diverse uses across different industries.
Used in Chiral Building Blocks Production:
Isopropylmalonic acid is used as a precursor in the production of chiral building blocks, which are crucial for the synthesis of enantiomerically pure compounds, essential in various chemical and pharmaceutical processes.

InChI:InChI=1/C6H10O4/c1-3(2)4(5(7)8)6(9)10/h3-4H,1-2H3,(H,7,8)(H,9,10)/p-2

Upstream product

• 75-30-9 2-iodo-propane 
• 996-82-7 sodium diethylmalonate 
• 55459-50-2 isopropylmalonyl dichloride 
• 30989-71-0 2-diethoxymethyl-1,1-diethoxy-3-methylbutane 
• 72651-95-7 5-isopropyl-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 108-12-3 isopentanoyl chloride 
• 103495-93-8 2-isopropyl-3-methoxy-3-oxopropanoic acid 
• 543-27-1 isobutyl chloroformate 
• 2033-24-1 cycl-isopropylidene malonate 
• 67-63-0 isopropyl alcohol 
• 759-36-4 diethyl isopropylmalonate 
• 51122-91-9 dimethyl isopropylmalonate 
• 4431-61-2 2-isopropyl-malonamic acid 
• 7782-77-6 cis-nitrous acid 

Downstream Products

• 51122-91-9 dimethyl isopropylmalonate 
• 7358-62-5 1,3-dimethyl-5-isopropylbarbituric acid 
• 503-74-2 3-methylbutyric acid 
• 15719-64-9 methylammonium carbonate 
• 921-08-4 2-chloro-3-methylbutanoic acid 
• 860375-51-5 isopropyl-malonic acid diphenyl ester 
• 16797-40-3 3-isopropyl-5-phenyl-1-oxa-5-aza-spiro[5.5]undecane-2,4-dione 
• 1215-09-4 5-isopropyl-2-phenyl-[1,3]oxazine-4,6-dione 
• 122778-25-0 (1R,3R,4S)-p-menthan-3-yl hydrogen isopropylmalonate 
• 111042-78-5 (1R,3R,4S)-8-phenyl-p-menthan-3-yl hydrogen isopropylmalonate 
• 94330-56-0 Isopropylmalonsaeure-bis-(2,4-dichlorphenylester) 
• 74610-79-0 5-isopropyl-5-(p-methoxyphenyl)-2,2-dimethyl-1,3-dioxan-4,6-dione 
• 15071-36-0 (2S)-(+)-2,3-dimethyl-1-butanol 
• 122778-53-4 (S)-2,3-Dimethyl-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 

Relevant academic research and scientific papers

Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates

An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.

Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation

The rhodium(III)-catalyzed coupling of C-H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C-H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol % in a gram-scale reaction. Representative products exhibit cytotoxicity toward human cancer cells at nanomolar levels.

Exploring the Promiscuous Enzymatic Activation of Unnatural Polyketide Extender Units in Vitro and in Vivo for Monensin Biosynthesis

The incorporation of new-to-nature extender units into polyketide synthesis is an important source for diversity yet is restricted by limited availability of suitably activated building blocks in vivo. We here describe a straightforward workflow for the biogenic activation of commercially available new-to-nature extender units. Firstly, the substrate scope of a highly flexible malonyl co-enzyme A synthetase from Streptomyces cinnamonensis was characterized. The results were matched by in vivo experiments in which the said extender units were accepted by both the polyketide synthase and the accessory enzymes of the monensin biosynthetic pathway. The experiments gave rise to a series of predictable monensin derivatives by the exploitation of the innate substrate promiscuity of an acyltransferase and downstream enzyme functions.

Computational and experimental studies on copper-mediated selective cascade C-H/N-H annulation of electron-deficient acrylamide with arynes

An efficient and convenient copper-mediated method has been developed to achieve direct cascade C-H/N-H annulation to synthesize 2-quinolinones from electron-deficient acrylamides and arynes. This method highlights an emerging but simple strategy to transform inert C-H bonds into versatile functional groups in organic synthesis to provide a new method of synthesizing 2-quinolinones efficiently. Mechanistic investigations by experimental and density functional theory (DFT) studies suggest that an organometallic C-H activation via a Cu(iii) intermediate is likely to be involved in the reaction.

Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling

A Ni-catalyzed enantioselective reductive diarylation of activated alkenes by domino cyclizative/cross-coupling of two aryl bromides is developed. This reaction proceeds under very mild conditions and shows broad substrate scope, without requiring the use of preformed organometallic reagents. Moreover, this approach provides direct access to various bis-heterocycles bearing all-carbon quaternary centers in synthetically useful yields (up to 81%) with excellent enantioselectivity (>30 examples, 90-99% ee).

Bifunctional Iminophosphorane Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α-Substituted Acrylate Esters

The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated α-substituted acrylate esters catalyzed by a bifunctional iminophosphorane organocatalyst under mild conditions is described. The strong Br?nsted basicity of the iminophosphorane moiety of the catalyst provides the necessary activation of the alkyl thiol pro-nucleophile, while the two tert-leucine residues flanking a central thiourea hydrogen-bond donor facilitate high enantiofacial selectivity in the protonation of the transient enolate intermediate. The reaction is broad in scope with respect to the alkyl thiol, the ester moiety, and the α-substituent of the α,β-unsaturated ester, affords sulfa-Michael adducts in excellent yields (up to >99%) and enantioselectivities (up to 96% ee), and is amenable to decagram scale-up using catalyst loadings as low as 0.05 mol %.

PROCESS FOR PREPARING BETA- (FLUOROPHENYL) -PROPANOATE ESTER DERIVATIVES

A process for preparing a compound of formula (I) comprising reacting a compound of formula (II) with a fluorinated boron species of formula (III) in the presence of: an alcohol; a rhodium (I) pre-catalyst species; a suitable ligand that binds to the rhodium (I) pre-catalyst species to form a catalyst complex; a base; and, a suitable solvent; the process being carried out at a temperature in the range 40 to 110oC. The compounds of formula (I) are useful in the preparation of pharmaceutically active compounds.

Microwave assisted hydrolysis of Meldrum's acid derivatives and decarboxylation of derived malonic acids

Microwave induced hydrolysis of alkyl Medrum's acids and decarboxylation of derived malonic acids using poly-4-vinylpyridine as a catalyst gives high yields of carboxylic acids in a short time.

Antiretroviral hydrazine derivatives

The invention relates to compounds of formula STR1 and salts, pharmaceutical compositions, intermediates and processes of preparation thereof.