41051-15-4

Basic information

• Product Name: Methyl 4-methoxyacetoacetate
• Synonyms: 4-methoxy-3-oxo-butanoicacimethylester;Butanoic acid, 4-methoxy-3-oxo-, methyl ester;Methyl methoxyacetoacetate;METHYL 4-METHOXYACETOACETATE;METHYL 4-METHOXYACETOXYACETATE;METHYL 4-METHOXY-3-OXO-BUTANOATE;4-METHOXYACETOACETIC ACID METHYL ESTER;methyl 4-methoxy-3-oxobutyrate
• CAS NO: 41051-15-4
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.14
• EINECS: 255-188-9
• Product Categories: Acetics acid and esters;C6 to C7;Carbonyl Compounds;Esters
• Mol File: 41051-15-4.mol

Chemical Properties

• Melting Point: -80℃
• Boiling Point: 89 °C8.5 mm Hg(lit.)
• Flash Point: 193 °F
• Appearance: colorless to yellow liquid
• Density: 1.129 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.146mmHg at 25°C
• Refractive Index: n20/D 1.431(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.88±0.46(Predicted)
• BRN: 1761215
• CAS DataBase Reference: Methyl 4-methoxyacetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-methoxyacetoacetate(41051-15-4)
• EPA Substance Registry System: Methyl 4-methoxyacetoacetate(41051-15-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 41051-15-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Methyl 4-methoxyacetoacetate is used as a reactant for the formation of an abiotic porphyrinogen in aqueous solution. This application highlights its utility in the synthesis of complex organic molecules and its potential role in the study of biological processes.
Used in Pharmaceutical Industry:
Methyl 4-methoxyacetoacetate is used as a key component in the generation of a small focused library of diversely functionalized dihydropyrimidine derivatives. This is achieved through a one-pot three-component Biginelli cyclocondensation of β-ketoesters, aldehydes, and (thio)ureas. The resulting dihydropyrimidine derivatives have potential applications in the development of new pharmaceuticals, particularly in the treatment of various diseases and conditions.

InChI:InChI=1/C6H10O4/c1-9-4-5(7)3-6(8)10-2/h3-4H2,1-2H3

Upstream product

• 6290-49-9 methyl methoxyacetate 
• 96-32-2 bromoacetic acid methyl ester 
• 17790-81-7 methyl 4-bromo-3-oxobutanoate 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 32807-28-6 Methyl 4-chloroacetoacetate 
• 382141-76-6 methyl 3-hydroxy-4-methoxybutanoate 
• 68665-45-2 4-methoxy-3-oxobutanoic acid 
• 107-03-9 1-thiopropane 
• 141-97-9 ethyl acetoacetate 
• 38330-80-2 monomethyl monopotassium malonate 
• 31059-08-2 1-(1H-imidazol-1-yl)-2-methoxyethanone 
• 105-45-3 acetoacetic acid methyl ester 
• 130895-62-4 methyl 2,4-dimethoxyacetoacetate 

Downstream Products

• 494202-82-3 2-amino-6-methoxymethyl-3H-pyrimidin-4-one 
• 104784-20-5 2-(2-Methoxy-acetyl)-4,5-dimethyl-hex-4-enoic acid methyl ester 
• 133902-69-9 4-methoxycarbonyl-5-methoxymethyl-1-phenyl-1,2,3-triazole 
• 192574-28-0 5-methoxycarbonyl-4-methoxymethyl-1,2,3,6-tetrahydro-2-oxo-6-(3,4-difluorophenyl)-pyrimidine 
• 252002-09-8 5-methoxycarbonyl-4-methoxymethyl-2-oxo-1,2,3,6-tetrahydro-6-(3,4,5-trifluorophenyl)pyrimidine 
• 252002-09-8 (+)-5-methoxycarbonyl-4-methoxymethyl-2-oxo-1,2,3,6-tetrahydro-6-(3,4,5-trifluorophenyl)pyrimidine 
• 209731-54-4 3-(3-cyanophenyl)-5-methoxymethyl-4-carbomethoxyisoxazole 
• 127958-19-4 4-(methoxymethyl)-2-phenylpyrimidine 
• 218430-63-8 (S)-4-(3,4-difluorophenyl)-1,2,3,4-tetrahydro-6-(methoxymethyl)-2-oxo-5-pyrimidinecarboxylic acid methyl ester 
• 220497-99-4 (S)-4-(3,4-difluorophenyl)-1,2,3,4-tetrahydro-6-(methoxymethyl)-2-oxo-5-pyrimidinecarboxylic acid 
• 153862-94-3 4-Methoxy-3-oxo-2-(p-tolyl-hydrazono)-butyric acid methyl ester 
• 153862-92-1 2-[(4-Chloro-phenyl)-hydrazono]-4-methoxy-3-oxo-butyric acid methyl ester 
• 153862-99-8 4-Methoxy-2-[(4-nitro-phenyl)-hydrazono]-3-oxo-butyric acid methyl ester 

Relevant articles and documents

Preparation method of methyl 4-methoxyacetoacetate

The invention discloses a preparation method of methyl 4-methoxyacetoacetate, belonging to the technical field of organic synthesis. According to the method, sodium methoxide is used as alkali, acetonitrile and methyl tert-butyl ether are used as a mixed solvent, and the reactant methyl 4-chloroacetoacetate is fed in stages, so a reaction temperature is reduced, ester hydrolysis byproducts are prevented from being generated, product quality is improved, production cost is greatly reduced, and economic benefits are improved.

Preparation method of 4-alkoxyacetoacetate compound

The invention discloses a preparation method of a 4-alkoxyacetoacetate compound, and the method comprises the following steps: reacting a compound I with a first alkali in a first solvent to obtain anintermediate II; reacting the intermediate II obtained in the step (1) with a second alkali in a second solvent to obtain an intermediate III; reacting the intermediate III obtained in the step (2) in an aqueous solution of acid to obtain a product IV, namely the 4-alkoxyacetoacetate compound, wherein X is chlorine, bromine or iodine; wherein R is a C1-C4 alkyl group and a derivative thereof. Thepreparation method provided by the invention has the advantages of simple steps, mild conditions, environmental friendliness, cheap and easily available raw materials, stable supply and low cost, andcreates favorable conditions for reducing the raw material cost of dolutegravir.

NEW ANALOGS AS ANDROGEN RECEPTOR AND GLUCOCORTICOID RECEPTOR MODULATORS

The present invention relates to novel dihydropyridine derivatives of formula (I): as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing's syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism.

Preparation process of methyl 4-methoxyacetoacetate

The invention discloses a preparation process of methyl 4-methoxyacetoacetate, comprising the following process steps: step 1, taking anhydrous toluene as a solvent, adding a methanol solution of sodium methoxide in the solvent as a base, at room temperature, dropwise adding methyl 4-chloroacetoacetate in the solvent, after dropwise adding, stirring, heating to 65-70 DEG C during stirring, and reacting for 3 to 5 hours to obtain a sodium salt of methyl 4-methoxyacetoacetate; step 2, acidifying the sodium salt, adjusting with acid to achieve the pH of 5-6, stirring for 30 min, and adjusting thepH to 3-4 to obtain a toluene layer and an aqueous layer, washing the toluene layer to neutral with a saturated sodium chloride solution, performing reduced pressure distillation to remove toluene and obtain a crude product of methyl 4-methoxyacetoacetate, and performing reduced pressure distillation on the crude product to obtain a target product with the purity of 99 percent. The invention discloses the preparation process of methyl 4-methoxyacetoacetate to realize effective, high-quality and low-cost synthesis.

Synthetic method of methyl 4-methoxyacetoacetate

The invention discloses a synthetic method of methyl 4-methoxyacetoacetate. The synthetic method comprises the following specific steps: (1) adding tetrahydrofuran into a reaction kettle, introducing an inert gas, controlling the internal temperature of the reaction kettle to be 15-25 DEG C, adding sodium hydride and potassium methoxide, adding tetrahydrofuran again, controlling the temperature of the system to be 20 DEG C, dropwise adding a mixed solution of methanol and methyl4-chloroacetoacetate for reaction for 4-6 hours, and heating up to 20-25 DEG C for continuous reaction for 3-5 hours; (2) cooling down to -5-0 DEG C, adding hydrochloric acid solution to adjust the pH value of the reaction system to be 10-12, and performing suction filtration on reaction liquid to obtain a white solid; and (3) adding the white solid into ethyl acetate, dropwise adding hydrochloric acid solution at 0 DEG C to adjust the pH of the reaction system to be 3-5, then performing suction filtration on the reaction liquid to separate out an organic layer from the filtrate, decolorizing an organic phase by using a decolorant, and then performing evaporation to remove the solvent, thereby obtaining a pure product namely methyl 4-methoxyacetoacetate. According to the synthetic method disclosed by the invention, reaction can be carried out at room temperature, and a product can be evaporated out at a relatively low temperature, so that the risk of the production process is directly and effectively reduced, and the impurity content of the product is reduced.

A 4 - methoxy methyl acetoacetate method for the preparation of

The invention discloses a 4-methoxy methyl acetoacetate preparation method. The 4-methoxy methyl acetoacetate preparation method comprises the following steps of adding a solvent tetrahydrofuran into a reaction kettle and leading inert gas into the reaction kettle, setting the internal temperature of the reaction kettle to be 15 DEG C to 25 DEG C, adding industrial sodium hydride and a metal alkaline compound in a stirring state, then adding the solvent tetrahydrofuran, dropwise adding mixed liquid of methyl alcohol and methyl-4-chloroacetoacetate at the temperature of lower than 20 DEG C to perform reaction for 4-6 hours, rising the temperature to be 20 DEG C to 25 DEG C to continue to react for 4-15 hours, reducing the system temperature to be 6 DEG C to 10 DEG C after TLC detection reaction is completed, adding a hydrochloric acid solution with molar concentration of 2 mol/L to regulate the pH of a system to be 5 to 7, performing standing and laying, concentrating and spin-drying upper-layer liquid to remove the solvent tetrahydrofuran after liquid separation and then obtaining a colorless product 4-methoxy methyl acetoacetate through wiped-film molecular distillation. The 4-methoxy methyl acetoacetate can react at room temperature, a product can be produced at low temperature through distillation, and dangerousness in the production process and product impurity content can be directly and effectively reduced.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF PERIODONTITIS AND RHEUMATOID ARTHRITIS

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of periodontitis and rheumatoid arthritis may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection.

Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4- naphthoquinones via one-pot aryne acyl-alkylation/condensation

A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP. The Royal Society of Chemistry 2009.

Method for preparing chiral diphosphines

The invention concerns a method for preparing a compound of formula (1) wherein: A represents naphthyl or phenyl optionally substituted; and Ar1, Ar2independently represent a saturated or aromatic carbocyclic group, optionally substituted.