21633-78-3

Usage

Uses

Diethylisobutyroylmalonate is a useful compound for preparing housefly GABA receptors.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 2622, 1985 DOI: 10.1021/jo00215a003

InChI:InChI=1/C11H18O5/c1-5-15-10(13)8(9(12)7(3)4)11(14)16-6-2/h7-8H,5-6H2,1-4H3

Upstream product

• 996-82-7 sodium diethylmalonate 
• 79-30-1 isobutyryl chloride 
• 105-39-5 chloroacetic acid ethyl ester 
• 7152-15-0 ethyl 4-methyl-3-oxo-pentanoate 
• 105-53-3 diethyl malonate 
• 35227-78-2 diethyl (ethoxymagnesio)malonate 
• 19967-55-6 1-bromo-3-methyl-2-butanone 

Downstream Products

• 67590-55-0 3-isopropyl-2,6,7-trioxa-1-phospha-bicyclo[2.2.2]octane 1-oxide 
• 778580-45-3 2-[1-(3-fluorophenyl)-2-methylpropylidene]malonic acid diethyl ester 
• 7152-15-0 ethyl 4-methyl-3-oxo-pentanoate 
• 10203-58-4 (2-methylpropyl)-propanedioic acid, diethyl ester 

Relevant academic research and scientific papers

Preparation process of isobutyryl ethyl acetate

The invention provides an isobutyryl ethyl acetate preparation process which is characterized by comprising the following specific steps: step one, adding 125 mL of ethyl acetate and 13.6 g (80 mmol)of potassium mono-ethyl malonate into a three-neck flask, stirring and cooling to 0-5 DEG C, then sequentially adding 9.12 g (96 mmol) of anhydrous magnesium chloride and 27.8 mL (0.2 mol) of triethylamine, heating to 65 DEG C within 0.5 h, and stirring for 6 hours at the temperature of 65 DEG C; step two, cooling to 0 DEG C, dropwise adding 6 mL (57 mmol) of isobutyryl chloride within one hour, and carrying out reactions at the room temperature for 12 hours; step three, cooling to 0 DEG C, carefully adding 70 mL of 13% hydrochloric acid, keeping the temperature not higher than 20 DEG C in theprocess; step four, separating out an organic phase, extracting a water layer with toluene (40 mL*3), merging the organic phase, washing with a saturated sodium bicarbonate solution until the organicphase is neutral, and washing with 25 mL of saturated edible salt water, and carrying out reduced pressure distillation to remove the solvent; and step five, carrying out reduced pressure distillation on the crude product to obtain 5.5 g of colorless liquid. The method provided by the invention solves the problems of low productivity and low purity during production and manufacturing of isobutyryl ethyl acetate at present.

Discovery of the bifunctional modulator of angiotensin II type 1 receptor (AT1R) and PPARγ derived from the AT1R antagonist, Fimasartan

Inspired by the well-known PPARγ partial agonism of angiotensin II type 1 receptor (AT1R) antagonists exemplified by an antihypertensive drug, Telmisartan, efforts to identify compounds with the dual activities have been pursued in order to control the two major metabolic disorders, hypertension and hyperglycemia simultaneously. Lead compound 18 derived from the AT1R antagonist, Fimasartan, has successfully presented the possibility to control the medical conditions by a single molecule.

Efficient palladium-catalyzed cross-coupling of β-chloroalkylidene/ arylidene malonates using microwave chemistry

A general method for the synthesis of β-aryl/ alkylarylidene malonates is reported. The key step involves the coupling of an arylboronic acid to a β-chloroalkyl/ arylidene malonate, in the presence of K2CO 3 and 1 mol % of the air-stable palladium catalyst (POPd) under microwave irradiation, to afford β-aryl/alkylarylidene malonates in good yields. The combination of mild reaction conditions, air stable catalyst, microwave-enhanced chemistry, and high levels of functional group compatibility make this an attractive synthetic approach to this class of compounds.

A synthesis of orixiarine

A synthesis of the quinoline alkaloid, orixiarine was achieved starting from N-methylaniline and isopropyl methyl ketone.

Bicyclophosphorothionate antagonists exhibiting selectivity for housefly GABA receptors

2,6,7-Trioxa-1-phosphabicyclo[2.2.2]octane 1-sulfides (bicyclophosphorothionates) with various C1-4 alkyl groups at the 3- and 4-positions were synthesized and tested for their ability to compete with [3H]4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB), a non-competitive antagonist of γ-aminobutyric acid (GABA) receptors, for specific binding to rat-brain and housefly-head membranes, and for their insecticidal activity against houseflies. Among the 3,4-substituted analogues, 20 compounds were selectively active for housefly GABA receptors versus rat GABA receptors. The 3-alkyl groups of C3 length and the 4-alkyl groups of C4 length were tolerated in housefly receptors, whereas such bulky substituents were deleterious in rat receptors. The 4-isobutyl-3-isopropyl analogue was the most potent in housefly receptors (IC50 = 45.2 nM), and tert- butylbicyclophosphorothionate (TBPS), with the 4-tert-butyl group and no 3- substituent, was the most potent in rat receptors (IC50 = 62.2 nM). Their receptor selectivities (rat IC50/housefly IC50) were 52 and 0.038, respectively. The insecticidal activity (LD50) of 20 active analogues was well correlated with their potency (IC50) in inhibiting [3H]EBOB binding to housefly-head membranes (r = 0.93). The results obtained in the present study indicate that the introduction of appropriate alkyl groups into the 3- and 4-positions of bicyclophosphorothionate leads to non-competitive antagonists with increased affinity and selectivity for housefly ionotropic GABA receptors versus rat GABA(A) receptors.

Procedures for the Acylation of Diethyl Malonate and Ethyl Acetoacetate with Acid Chlorides Using Tertiary Amine Bases and Magnesium Chloride

In the presence of magnesium chloride and 2 equiv of triethylamine, diethyl malonate is C-acylated in excellent yields by acid chlorides.A variety of other metal chlorides were ineffective.Similarly, ethyl acetoacetate is C-acylated by acid chlorides in the presence of magnesium chloride and 2 equiv of pyridine.