932-90-1

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 932-90-1 differently. You can refer to the following data:
1. Oximes are used as a peel-preventing additive in paints and lacquers. It acts as an antioxidant against oxidative drying materials which forms sticky skin with air oxygen. Oximes are used as chemical building block for the synthesis of agrochemicals and pharmaceuticals. In medicine application, Oxime structure is effective in cholinesterase reactivators to treat the poisoning by organophosphates. Oxime is used as a ligand in transition-metal complex catalyst chemistry. Oxime acts as an antioxidant, radical scavenger which find applications in textile, plastic, paint, detergent, and rubber industry.
2. Benzaldoxime is an intermediate used to prepare Δ2-Isoxazoline derivatives as DNA methyltransferase 1 inhibitors. It is also used in the synthesis of potent 1,2,4-Oxadiazole EthR inhibitors.

Synthesis Reference(s)

Tetrahedron, 51, p. 11305, 1995 DOI: 10.1016/0040-4020(95)00692-2Tetrahedron Letters, 36, p. 1903, 1995 DOI: 10.1016/0040-4039(95)00108-O

Purification Methods

Crystallise the oxime from diethyl ether by adding pet ether (b 60-80o). The syn-isomer [622-32-2] has b 121-124o/12mm, m 34-36o. [Beilstein 7 H 218, 7 IV 527.]

InChI:InChI=1/C7H7NO/c9-8-6-7-4-2-1-3-5-7/h1-6,9H/b8-6-

Upstream product

• 64-17-5 ethanol 
• 12321-46-9 phenylnitromethane sodium salt 
• 100-44-7 benzyl chloride 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 75735-29-4 (E)-O-(2,4-dinitrophenyl)benzaldoxime 
• 108-91-8 cyclohexylamine 
• 100-52-7 benzaldehyde 
• 100-47-0 benzonitrile 
• 71-43-2 benzene 
• 614-21-1 2-nitroacetophenone 
• 100-39-0 benzyl bromide 
• 98-07-7 Benzotrichlorid 
• 100-46-9 benzylamine 
• 102-97-6 Benzyl-isopropyl-amin 

Downstream Products

• 103639-81-2 benzaldehyde-(O-diethoxyphosphoryl oxime ) 
• 16430-09-4 3-methyl-4-(1-phenylmethylidene)-5-isoxazolone 
• 1088-32-0 3-phenyl-4-(1-phenylmethylidene)-5-isoxazolone 
• 6343-54-0 N-benzylformamide 
• 65655-88-1 3-hydroxy-2-phenyl-thiazolidin-4-one 
• 22892-77-9 benzaldehyde O-allyl oxime 
• 19433-13-7 O-Acetylbenzaldoxim 
• 65616-27-5 N-propyl-N-benzylhydroxylamine 
• 52605-62-6 triphenyl-(3-phenyl-isoxazol-5-ylmethyl)-phosphonium; bromide 
• 22892-67-7 O-<2-Propyl>-benzaldoxim 
• 69373-62-2 C₂₆H₂₂N₂O₂Si 
• 17876-73-2 O-(trimethylsilyl)benzaldoxime 
• 65616-29-7 N-benzyl-N-isopropylhydroxylamine 
• 41542-48-7 N-Hydroxy-thiobenzimidic acid 2-diethylamino-ethyl ester 

Relevant academic research and scientific papers

Nickel-Catalyzed NO Group Transfer Coupled with NOxConversion

Nitrogen oxide (NOx) conversion is an important process for balancing the global nitrogen cycle. Distinct from the biological NOx transformation, we have devised a synthetic approach to this issue by utilizing a bifunctional metal catalyst for producing value-added products from NOx. Here, we present a novel catalysis based on a Ni pincer system, effectively converting Ni-NOx to Ni-NO via deoxygenation with CO(g). This is followed by transfer of the in situ generated nitroso group to organic substrates, which favorably occurs at the flattened Ni(I)-NO site via its nucleophilic reaction. Successful catalytic production of oximes from benzyl halides using NaNO2 is presented with a turnover number of >200 under mild conditions. In a key step of the catalysis, a nickel(I)-?NO species effectively activates alkyl halides, which is carefully evaluated by both experimental and theoretical methods. Our nickel catalyst effectively fulfills a dual purpose, namely, deoxygenating NOx anions and catalyzing C-N coupling.

Cyanide-Free Cyanation of Aryl Iodides with Nitromethane by Using an Amphiphilic Polymer-Supported Palladium Catalyst

A cyanide-free aromatic cyanation was developed that uses nitromethane as a cyanide source in water with an amphiphilic polystyrene poly(ethylene glycol) resin-supported palladium catalyst and an alkyl halide (1-iodobutane). The cyanation proceeds through the palladium-catalyzed cross-coupling of an aryl halide with nitromethane, followed by transformation of the resultant (nitromethyl)arene intermediate into a nitrile by 1-iodobutane.

Visible-light mediated stereospecific C(sp2)-H difluoroalkylation of (Z)-aldoximes

A visible light mediated stereospecific C(sp2)-H difluoroalkylation of (Z)-aldoximes to (E)-difluoroalkylated ketoximes has been described. In this reaction, (hetero)-aromatic and aliphatic difluoroalkylated ketoximes could be obtained with the retention of the configuration of the starting aldoximes. A preliminary mechanism study showed that a difluoromethyl radicalviaan SET pathway was involved.

Novel oxime derivative and application thereof in agriculture

The present invention relates to a novel oxime derivative and application thereof in agriculture. The novel oxime derivative has a structure represented by formula (I), wherein R, R, R, R and R are each independently hydrogen, fluorine, chlorine or the like, A is shown as the specification, wherein R and R are each independently hydrogen, C1-4 alkyl group, phenyl group or the like, R is C1-4 alkoxy group or the like, and R is hydrogen or C1-4 alkyl group. The novel oxime derivative disclosed by the invention is novel in structure and simple in synthesis process, and has an excellent control effect on plant diseases, particularly cucumber downy mildew.

Visible-Light-Mediated Strategies for the Preparation of Oxime Ethers Derived from O-H Insertions of Oximes into Aryldiazoacetates

Two visible-light-mediated O-H insertion protocols involving oximes and aryldiazoacetates leading to different products depending on the solvent employed are reported. In DCM, direct O-H insertion takes place. In THF, there is the additional incorporation of the ring-opened form of this solvent into the structure of the product. These metal-free protocols are mild and tolerant to air and moisture. The preparation of an acaricide has been developed as an example of synthetic application.

Dioxido-vanadium(V) complex catalyzed oxidation of alcohols and tandem synthesis of oximes: a simple catalytic protocol for C–N bond formation

We report the synthesis of a vanadium(V) complex characterized by FT-IR and 1H NMR spectroscopy. The structure of the complex was established by single crystal X-ray crystallography. We also carried out the catalytic oxidation of benzyl alcohol, hetero-aryl alcohols and propargylic alcohols. Tandem synthesis of oximes from alcohols were also carried out using our vanadium(V) complex. The newly synthesized complex acts as a catalyst for oxidation reactions and tandem synthesis of oxime from alcohols.

Synthesis and Biological Activity of 2-(2-Amino-2-phenylethyl)-5-oxotetrahydrofuran-2-carboxylic Acid: A Microwave-Assisted 1,3-Dipolar Cycloaddition Approach

The microwave-assisted 1,3-dipolar cycloaddition of furanyl and benzyl oximes and several methyl acrylates effectively provided several isoxazoline when mediated by diacetoxyiodobenzene. The selected isoxazoline, methyl-5-(3-methoxy-3-oxopropyl)-3-phenyl-4,5-dihydro isoxazole-5-carboxylate, was rapidly transformed to the γ-lactone carboxylic acid, 2-(2-amino-2-phenylethyl)-5-oxotetrahydrofuran-2-carboxylic acid, in reasonable yield. The biological activity of this γ-lactone carboxylic acid increased the growth of E. coli organisms by about 44% and has a potential significance in stem cell research.

Design, synthesis, and biological evaluation of N-(4-substituted)-3-phenylisoxazolo[5,4–d]pyrimidin-4-amine derivatives as apoptosis-inducing cytotoxic agents

A library of new 3-phenylisoxazolo[5,4–d]pyrimidines (8–10) was designed based on a scaffold hybridization technique incorporating the important pharmacophoric features of 4-aminopyrimidine and phenyl isoxazole scaffold which is renowned for its BET inhib

Poly(N-vinylimidazole): A biocompatible and biodegradable functional polymer, metal-free, and highly recyclable heterogeneous catalyst for the mechanochemical synthesis of oximes

The catalytic activity of poly(N-vinylimidazole), a biocompatible and biodegradable synthetic functional polymer, was investigated for the synthesis of oximes as an efficient, halogen-free, and reusable heterogeneous catalyst. The corresponding oximes were afforded in high to excellent yields at room temperature and in short times using the planetary ball mill technique. Some merits, such as the short reaction times and good yields for poorly active carbonyl compounds, and avoiding toxic, expensive, metal-containing catalysts, and hazardous and flammable solvents, can be mentioned for the current catalytic synthesis of the oximes. Furthermore, the heterogeneous organocatalyst could be easily separated after the reaction, and the regenerated catalyst was reused several times with no significant loss of its catalytic activity.

Design, synthesis and biological evaluation of novel indanone containing spiroisoxazoline derivatives with selective COX-2 inhibition as anticancer agents

Objective: A new family of 3′-(Mono, di or tri-substituted phenyl)-4′-(4-(methylsulfonyl) phenyl) spiroisoxazoline derivatives containing indanone spirobridge was designed, synthesized, and evaluated for their selective COX-2 inhibitory potency and cytotoxicity on different cell lines. Methods: A synthetic reaction based on 1,3-dipolar cycloaddition mechanism was applied for the regiospecific formation of various spiroisoxazolines. The activity of the newly synthesized compounds was determined using in vitro cyclooxygenase inhibition assay. The toxicity of the compounds was evaluated by MTT assay. In addition, induction of apoptosis, and expression levels of Bax, Bcl-2 and caspase-3 mRNA in MCF-7 cells were evaluated following exposure to compound 9f. The docking calculations and molecular dynamics simulation were performed to study the most probable modes of interactions of compound 9f upon binding to COX-2 enzyme. Results: The docking results showed that the synthesized compounds were able to form hydrogen bonds with COX-2 involving methyl sulfonyl, spiroisoxazoline, meta-methoxy and fluoro functional groups. Spiroisoxazoline derivatives containing methoxy group at the C-3′ phenyl ring meta position (9f and 9g) showed superior selectivity with higher potency of inhibiting COX-2 enzyme. Furthermore, compound 9f, which possesses 3,4-dimethoxyphenyl on C-3′ carbon atom of isoxazoline ring, exhibited the highest COX-2 inhibitory activity, and also displayed the most potent cytotoxicity on MCF-7 cells with an IC50 value of 0.03 ± 0.01 μM, comparable with that of doxorubicin (IC50 of 0.062 ± 0.012 μM). The results indicated that compound 9f could promote apoptosis. Also, compared to the control group, the mRNA expression of Bax and caspase-3 significantly increased, while that of Bcl-2 significantly decreased upon exposure to compound 9f which may propose the activation of mitochondrial-associated pathway as the mechanism of observed apoptosis. Conclusion: In vitro biological evaluations accompanied with in silico studies revealed that indanone tricyclic spiroisoxazoline derivatives are good candidates for the development of new anti-inflammatory and anticancer (colorectal and breast) agents.