10312-37-5

Usage

Uses

Used in Organic Synthesis:
4-Nitrovaleric acid methyl ester is used as a building block in organic synthesis for the creation of various organic compounds. Its unique structure allows for the formation of a wide range of chemical entities, making it a valuable component in the synthesis process.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4-Nitrovaleric acid methyl ester is utilized as an intermediate in the production of various drugs. Its reactivity and functional groups enable the synthesis of biologically active molecules, contributing to the development of new medications.
Used in Agrochemical Production:
4-Nitrovaleric acid methyl ester also finds application in the agrochemical sector, where it serves as an intermediate for the synthesis of pesticides and other agricultural chemicals. Its role in this industry is crucial for the development of effective and targeted agrochemicals.
Used in Dye Production:
In the dye industry, 4-Nitrovaleric acid methyl ester is employed as an intermediate for the synthesis of various dyes. Its chemical properties allow for the creation of a diverse array of colorants, enhancing the range of dyes available for different applications.
Used in Medical Research:
4-Nitrovaleric acid methyl ester is used as a precursor in medical research for the synthesis of biologically active molecules. Its potential in this field is significant, as it can contribute to the discovery and development of new therapeutic agents and diagnostic tools.

InChI:InChI=1/C6H11NO4/c1-5(7(9)10)3-4-6(8)11-2/h5H,3-4H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 109178-35-0 4-bromo-4-nitro-valeric acid methyl ester 
• 127-08-2 potassium acetate 
• 79-24-3 Nitroethane 
• 121-44-8 triethylamine 
• 292638-85-8 acrylic acid methyl ester 
• 3395-91-3 Methyl 3-bromopropionate 
• 79-10-7 acrylic acid 

Downstream Products

• 83565-97-3 6-Benzenesulfinyl-4-methyl-4-nitro-hexanoic acid methyl ester 
• 143957-88-4 (Z)-α-Phenyl-N-(1-carbomethoxy-3-butyl)nitrone 
• 108-27-0 5-methylpyrrolidin-2-one 
• 93338-64-8 methyl 4-aminopentanoate 
• 123-76-2 levulinic acid 
• 86958-65-8 4-Methyl-4-nitro-5-(2-nitro-phenyl)-pentanoic acid methyl ester 
• 83566-00-1 6-Benzenesulfinyl-4-methyl-hexanoic acid methyl ester 
• 1381984-87-7 C₁₄H₁₉NO₅ 
• 186903-41-3 (S)-4-tert-Butoxycarbonylamino-pentanoic acid methyl ester 
• 214402-34-3 Boc-(R)-γ⁴-Ala-OH 
• 927-55-9 (±)-4-amino-1-pentanol 
• 525-61-1 primaquine 
• 86958-64-7 4-Methyl-4-nitro-5-(4-nitro-phenyl)-pentanoic acid methyl ester 
• 624-45-3 levulinic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of γ-nitro aliphatic methyl esters via michael additions promoted by microwave irradiation

A simple and efficient protocol has been developed for the direct synthesis of γ-nitrobutyric acid methyl esters under microwave irradiation. This methodology reduces reaction times from days to minutes, compared to conventional conditions. Additionally, these conditions increased yields and provided cleaner reactions.

Surface-Mediated Phase Reaction: Dramatic Improvement of Michael Reaction on the Surface of Alumina

The Michael reaction of several 1,3-dicarbonyl compounds, nitroalkanes, and thiols as donors with methl vinyl ketone, acrolein, methyl acrylate, methyl methacrylate, and mesityl oxide as acceptors on the surface of alumina without any solvent proceed very efficiently and furnish high yield of adducts. Key Words: Michael reaction; Al2O3; dramatic improvement

Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds

A basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [bmIm]OH, catalyzes the Michael addition of active methylene compounds to conjugated ketones, carboxylic esters and nitriles. It further catalyzes the addition of thiols to α,β-acetylenic ketones and alkylation of 1,3-dicarbonyl and -dicyano compounds. The Michael addition to α,β-unsaturated ketones proceeds in the usual way, giving the monoaddition products, whereas addition to α,β-unsaturated esters and nitriles leads exclusively to the bis-addition products. The α,β-acetylenic ketones undergo double conjugate addition with thiols producing β-keto 1,3-dithio-derivatives. In the alkylation reaction the acyclic 1,3-diketones are monoalkylated, whereas cyclic ketones undergo dialkylation under identical conditions. All these reactions were carried out without any organic solvent. The ionic liquid can also be recycled.

Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmIm]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles

(Chemical Equation Presented) A task-specific ionic liquid, [bmIm]OH, has been introduced as a catalyst and as a reaction medium in Michael addition. Very interestingly, although the addition to α,β-unsaturated ketones proceeds in the usual way, giving the monoaddition products, this ionic liquid always drives the reaction of open-chain 1,3-dicarbonyl compounds with α,β-unsaturated esters and nitriles toward bis-addition to produce exclusively bis-adducts in one stroke.

Effect of the Substituent and Amino Group Position on the Lipase-Catalyzed Resolution of γ-Amino Esters: A Molecular Docking Study Shedding Light on Candida antarctica lipase B Enantioselectivity

The kinetic resolution of N-tert-butoxycarbonyl γ-amino methyl esters bearing different stereocenters at alpha (γ2), beta (γ3), or gamma (γ4) positions was carried out by enantioselective hydrolysis with Candida antarctica lipase B (CaLB) in 2-methyl-2-butanol solvent. The results show that the process is significantly less enantioselective for the γ2-amino methyl ester (E=2.5), the γ3-amino methyl ester (E=7.6), and the γ4-amino methyl ester (E=8.3) when compared with the kinetic resolution of analogous N-protected β3-amino esters (E>80). Based on these results, molecular docking studies were carried out, through which particular regions in the CaLB catalytic cavity were analyzed. The steric exclusion region composed of Ile189 and Val190 residues, together with the amino bonding region that induces a hydrogen bond with the Asp134 residue, appear to be responsible for the high selectivity in the resolution of carboxylic acid derivatives with beta stereocenters. This interaction is well preserved for β-amino esters as substrates. By contrast, γ-amino esters exhibit greater conformational diversity, so the effectiveness of the interaction is reduced, which apparently is responsible for the loss of enantioselectivity in the resolution process.

APOPTOSIS SIGNAL-REGULATING KINASE INHIBITORS AND USES THEREOF

Described herein are ASK1 inhibitors and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for the treatment of blood disease, autoimmune disorders, pulmonary disorders, hypertension, inflammatory diseases, fibrotic diseases, diabetes, diabetic nephropathy, renal diseases, respiratory diseases, cardiovascular diseases, acute lung injuries, acute or chronic liver diseases, and neurodegenerative diseases.

Synthesis of Isoxazolines from Nitroalkanes via a [4+1]-Annulation Strategy

A novel access to isoxazolines was developed using the [4+1]-annulation of α-keto-stabilized sulfur ylides with N,N-bis(siloxy)enamines derived from aliphatic nitro compounds. The resulting 5-keto-substituted isoxazolines were shown to be convenient precursors of polysubstituted 3-hydroxypyrrolidines via the one-pot catalytic N?O hydrogenolysis/intramolecular reductive amination sequence. Application of this approach to the formal synthesis of Merck's potent NK1 receptor antagonist was demonstrated. (Figure presented.).

Solvent-Free Henry and Michael Reactions with Nitroalkanes Promoted by Potassium Carbonate as a Versatile Heterogeneous Catalyst

The use of a simple weak inorganic base such as potassium carbonate facilitated the formation of carbon-carbon bonds through both the Henry and the Michael reactions with nitrocompounds. The application of this catalyst under environmentally friendly solventless heterogeneous conditions gave satisfactory to good yields of β-nitroalcohols, involving aliphatic and aromatic starting materials, as well as high to excellent yields in the formation of Michael adducts using several different Michael acceptors and nitroalkanes.

Quinocide and preparation method of hydrochloride thereof

The invention discloses quinocide and a preparation method of hydrochloride thereof and belongs to the field of drug chemical research. According to the method, nitroethane and methyl acrylate serve as initial raw materials, and a Michael condensation reaction, formic ester removing, acyl chlorination, amidation, carbonyl reduction, nitro reduction, amino hydrochloric acid salinization and other reactions are sequentially performed so that quinocide and hydrochloride thereof can be prepared. The preparation method is easy to operate, raw materials are low in price, cost is low, the yield is high and reaches 94% or above, and industrial production can be achieved easily.

CuCN catalyzed one pot synthesis of γ-keto diesters: Domino double Michael addition followed by Nef reaction

An efficient one pot synthesis of γ-keto diesters through double Michael addition coupled with Nef reaction in the presence of CuCN catalyst and Cs2CO3 base is described. The reaction proceeds rapidly in DCM to give the products in good yields. A plausible mechanism is proposed.