22020-87-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Nitro-2-pentanone is used as a synthetic intermediate for the production of various pharmaceuticals, leveraging its reactivity and the presence of the nitro group to facilitate the creation of a range of medicinal compounds.
Used in Organic Synthesis:
In the field of organic chemistry, 5-Nitro-2-pentanone serves as a key reagent in organic reactions, particularly for the synthesis of nitrogen-containing organic compounds. Its ability to participate in a variety of reaction types makes it a valuable asset in the synthesis of complex organic molecules.
Used as a Building Block in Chemical Industries:
The versatility of 5-Nitro-2-pentanone, stemming from its nitro functionality, positions it as an essential building block in the chemical industry for the development of a diverse array of chemical products.

InChI:InChI=1/C5H9NO3/c1-5(7)3-2-4-6(8)9/h2-4H2,1H3

Upstream product

• 75-52-5 nitromethane 
• 590-90-9 1-Hydroxy-3-butanone 
• 124-41-4 sodium methylate 
• 2543-57-9 1-Dimethylamino-3-butanon 
• 35223-55-3 2-methyl-1,5-dinitro-pentan-2-ol 
• 78-94-4 methyl vinyl ketone 
• 25854-38-0 sodium nitromethane 
• 122876-03-3 5-nitro-5-(phenylsulfonyl)pentan-2-one 
• 83-34-1 3-Methylindole 
• 251955-05-2 [2-chloro-1-(methoxymethyl)-1H-indol-3-yl]-1H-indol-2-yl methanone 
• 35223-51-9 2-methyl-1-nitro-2-nitrooxy-pentane 
• 614-21-1 2-nitroacetophenone 
• 23542-51-0 5-nitropent-1-ene 
• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 

Downstream Products

• 173409-84-2 3-(1-Nitro-4-oxo-pent-1-yl)-cyclohexan-1-one 

Relevant academic research and scientific papers

TRANSFORMATION OF 4-NITROALKANE-1,7-DIONES INTO PYRROLIZIDINES

Depending on the conditions the reduction of 5-nitropentadecane-2,8-dione (4) gave as main products the two isomeric pyrrolizidines 1a (xenovenine, NaBH3CN/NH4OAc; as 15N-1a with NaBH3CN/15NH4OAc) and 1b (H2-Pd/C), respectively)

Michael additions in aqueous media: "on-water" and "in-water" processes from α-nitro ketones and their anions

A variety of α,β-unsaturated aldehydes and ketones gave very high-yielding Michael addition reactions with α-nitrocycloalkanones in water, at room temperature without added catalyst. These can be considered as one of the very few "on-water" Michael reacti

SYNTHESIS OF (+/-)-PYRENOPHORIN UTILIZING 1,3-DIPOLAR CYCLOADDITION OF SILYL NITRONATE FOR THE CONSTRUCTION OF 16-MEMBERED RING

1-Methyl-4-nitrobutyl acrylate underwent 1,3-dipolar cycloaddition via its silyl nitronate to give isoxazoline derivative of 16-membered dilactone after acid treatment, from which (+/-)-pyrenophorin was synthesized.

Origin of "Hetero Effect" on Nitrogen Inversion. Comparison of Hydroxylamines and Aminoxide Anions

Rate constants for nitrogen inversion in N-benzyl-N-methylhydroxylamine, N,N-diethylhydroxylamine, 1-hydroxy-2,2,4,4-tetramethylpyrrolidine, their conjugate bases, and their O-acetyl derivatives in dimethylformamide-d7 were determined based on the 1H NMR

A Modular and Diastereoselective 5 + 1 Cyclization Approach to N-(Hetero)Aryl Piperidines

A new general de novo synthesis of pharmaceutically important N-(hetero)aryl piperidines is reported. This protocol uses a robustly diastereoselective reductive amination/aza-Michael reaction sequence to achieve rapid construction of complex polysubstituted ring systems starting from widely available heterocyclic amine nucleophiles and carbonyl electrophiles. Notably, the diastereoselectivity of this process is enhanced by the presence of water, and DFT calculations support a stereochemical model involving a facially selective protonation of a water-coordinated enol intermediate.

Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts

The Br?nsted basicities pKaH (i.e., pKa of the conjugate acids) of 32 pyrrolidines and imidazolidinones, commonly used in organocatalytic reactions, have been determined photometrically in acetonitrile solution using CH acids as indicators. Most investigated pyrrolidines have basicities in the range 16 aH aH aH 12.6) and the 2-imidazoliummethyl-substituted pyrrolidine A21 (pKaH 11.1) are outside the typical range for pyrrolidines with basicities comparable to those of imidazolidinones. Kinetics of the reactions of these 32 organocatalysts with benzhydrylium ions (Ar2CH+) and structurally related quinone methides, common reference electrophiles for quantifying nucleophilic reactivities, have been measured photometrically. Most reactions followed second-order kinetics, first order in amine and first order in electrophile. More complex kinetics were observed for the reactions of imidazolidinones and several pyrrolidines carrying bulky 2-substituents, due to reversibility of the initial attack of the amines at the electrophiles followed by rate-determining deprotonation of the intermediate ammonium ions. In the presence of 2,4,6-collidine or 2,6-di-tert-butyl-4-methyl-pyridine, the deprotonation of the initial adducts became faster, which allowed the rate of the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log?k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale, which compares n-, -, and σ-nucleophiles. The nucleophilic reactivities of the title compounds correlate only poorly with their Br?nsted basicities.

Synergistic Noncovalent Catalysis Facilitates Base-Free Michael Addition

Carbon-carbon bond-forming processes that involve the deprotonation of a weakly acidic C-H pro-nucleophile using a strong Br?nsted base are central to synthetic methodology. Enzymes also catalyze C-C bond formation from weakly C-H acidic substrates; howev

Catalytic Asymmetric Synthesis of Isoxazolines from Silyl Nitronates

1,3-Dipolar cycloadditions of triisopropylsilyl nitronates and 2-alkylacroleins produced isoxazolines bearing a chiral quaternary center in high yields and enantioselectivities with the aid of a chiral oxazaborolidine catalyst. One chiral isoxazoline product was converted to (R)-(+)-Tanikolide in 9 steps in a total yield of 43%. (Chemical Equation Presented).

ALDEHYDE-SELECTIVE WACKER-TYPE OXIDATION OF UNBIASED ALKENES

This disclosure is directed to methods of preparing organic aldehydes, each method comprising contacting a terminal olefin with an oxidizing mixture comprising: (a) a dichloro-palladium complex; (b) a copper complex; (c) a source of nitrite; under aerobic reaction conditions sufficient to convert at least a portion of the terminal olefin to an aldehyde.

Aldehyde-selective wacker-type oxidation of unbiased alkenes enabled by a nitrite co-catalyst

Breaking the rules: Reversal of the high Markovnikov selectivity of Wacker-type oxidations was accomplished using a nitrite co-catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. 18O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt. Copyright