3376-32-7

Usage

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 1565, 1994 DOI: 10.1016/S0040-4039(00)76759-1

InChI:InChI=1/C8H9NO/c1-7-4-2-3-5-8(7)6-9-10/h2-6,10H,1H3/b9-6+

Upstream product

• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 20056-98-8 N-benzyl-N-methoxyamine 
• 3272-27-3 N-methoxy-urea 
• 141-97-9 ethyl acetoacetate 
• 593-56-6 N-methoxylamine hydrochloride 
• 1774-95-4 diethyl-N-methoxyphosphamide 
• 1569-76-2 N-methoxy-α-phenylnitrone 
• 67-62-9 O-Methylhydroxylamin 
• 67-56-1 methanol 
• 101854-96-0 1-(4-bromo-phenyl)-3-methoxyamino-3-phenyl-propan-1-one 

Downstream Products

• 1013-88-3 Benzophenone imine 
• 119-61-9 benzophenone 
• 91-00-9 Benzhydrylamine 
• 1415636-88-2 N-(3,4-dimethyl-1-phenylpent-3-en-1-yl)-N-methoxyacetamide 
• 1415637-00-1 (E)-1-methoxy-8-methyl-10-phenyl-3,4,5,6,9,10-hexahydroazecin-2(1H)-one 
• 1447827-00-0 2-((methoxyimino)methyl)benzonitrile 
• 1417412-48-6 2-benzoylbenzaldehyde O-methyl oxime 
• 552-89-6 2-nitro-benzaldehyde 
• 33499-33-1 3-nitrobenzaldoxime O-methyl ether 
• 55975-13-8 Ozonid des Benzyladamantans ⁽⁷⁾ 
• 103143-50-6 O-methylbenzohydroximoyl chloride 
• 34943-73-2 pentaammine(benzonitrile)ruthenium(II) hexafluorophosphate 
• 86370-67-4 (Z)-β-(2-pyridyl)-α-(trimethylsilylamino)styrene 
• 111515-28-7 N,N'-bis(isopropyl)benzamidine 

Relevant academic research and scientific papers

Compound and application thereof

The compound has the structure shown in the formula (I) or the formula (II) and R. 1 Selected from H. Deuterium, halogen, cyano, nitro, alkenyl, alkynyl, carboxy, C1 - C20 chain alkyl, C3 - C20 cycloalkyl, C1 - C20 alkoxy, substituted or unsubstituted C6 - C60 aryl, substituted or unsubstituted C3 - C60 heteroaryl, and the heteroatom in the heteroaryl is selected from O or S. L Is one selected from a single bond, a substituted or unsubstituted C6 - C60 arylene group, a substituted or unsubstituted C3 - C60 heteroarylene group. R Is one selected from H, deuterium, halogen, cyano, nitro, alkenyl, alkynyl, carboxy, C1 - C20 chain alkyl, C3 - C20 cycloalkyl, C1 - C20 alkoxy, substituted or unsubstituted C6 - C60 aryl, substituted or unsubstituted C3 - C60 heteroaryl. Ar Is a substituted or unsubstituted C6 - C60 aryl group, a substituted or unsubstituted C3 - C60 heteroaryl group. When the compound is applied OLED devices, the device efficiency can be effectively improved, the driving voltage is reduced, and the compound is a good-performance electronic transmission material.

Nickel-Catalyzed Transformation of Alkene-Tethered Oxime Ethers to Nitriles by a Traceless Directing Group Strategy

Nickel-catalyzed transformation of alkene-tethered oxime ethers to nitriles using a traceless directing group strategy has been developed. A series of alkene-tethered oxime ethers derived from benzaldehyde and cinnamyl aldehyde derivatives were converted into the corresponding benzonitriles and cinnamonitriles in 46-98% yields using the nickel catalyst system. Control experiments showed that the alkene group tethered to an oxygen atom on the oximes via one methylene unit plays a key role as a traceless directing group during the catalysis.

Nitrate promoted mild and versatile Pd-catalysed C(sp2)-H oxidation with carboxylic acids

A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp2)-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O-aryl esters. Moreover, the superiority of the nitrate additive in this mild transformation was further determined by experimental and computational evidence.

Synthesis of 2-fluorocholine aryl carbonyl compounds

The invention provides a method for synthesizing 2-fluoroarylcarbonyl compounds, which comprises the following steps: converting arylcarbonyl compounds into corresponding carbonyl oxime ether compounds, mildly implementing aryl hydrocarbon chain direct fluoridation of high-selectivity oximido substituent group ortho-position in the presence of a palladium catalyst, a fluoridation reagent and additives, and finally, rehydrolyzing oxime ethers under the action of acid to obtain the 2-fluoroarylcarbonyl compounds. The fluoridation method has the advantages of mild reaction conditions, high substrate adaptability, high fluoridation selectivity and the like, is simple to operate, and has higher application research value.

A O-nitrobenzaldehyde synthetic method of compound

The invention provides a preparation method for an o-nitrobenzaldehyde compound. The method directly taking benzaldehyde compounds as starting raw materials comprises the following steps: firstly, converting a formyl group into an O-methyl oximido; secondly, taking divalent palladium salt as a catalyst, and realizing the carbon-hydrogen bond activation single nitration reaction on an o-position of an oximido under the condition that both an oxidant and a nitration agent exist; finally, removing the O-methyl oximido by using strong organic acid to obtain the o-nitrobenzaldehyde compound. The nitration method provided by the invention has the advantage of specificity in the o-position of a nitration position, the reaction process is safe and environment-friendly, the substrate is excellent in adaptability, and various substituents can realize o-position nitration; various benzaldehyde is directly taken as raw materials, so that the reaction steps are simple, and the synthesizing method is a novel route for synthesizing various o-nitrobenzaldehyde compounds containing substituents.

An effective Biginelli-type synthesis of 1-methoxy-3,4-dihydropyrimidin-2(1H)-ones

Abstract The ternary condensation of N-methoxyurea, aldehydes, and 1,3-dicarbonyl compounds, resulting in novel 1-methoxy-3,4-dihydropyrimidin-2(1H)-ones has been examined. Commonly used reaction conditions and catalysts (EtOH/HCl, HOAc, DMF) proved to be

Palladium-catalyzed decarboxylative acylation of O-methyl ketoximes with α-keto acids

A mild, practical and efficient palladium-catalyzed decarboxylative ortho-acylation of O-methyl ketoximes with α-keto acids via C-H bond activation is described. In these reactions, a broad range of O-methyl ketoximes and α-keto acids undergoes the decarboxylative cross-coupling reactions with high selectivities and good tolerance. The Royal Society of Chemistry 2013.

Rhodium-catalyzed directed C-H cyanation of arenes with N-cyano-N-phenyl-p-toluenesulfonamide

A Rh-catalyzed directed C-H cyanation reaction was developed for the first time as a practical method for the synthesis of aromatic nitriles. N-Cyano-N-phenyl-p-toluenesulfonamide, a user-friendly cyanation reagent, was used in the transformation. Many different directing groups can be used in this C-H cyanation process, and the reaction tolerates a variety of synthetically important functional groups.

Palladium-catalyzed direct acylation of ketoximes and aldoximes from the alcohol oxidation level through C-H bond activation

A highly efficient palladium-catalyzed oxidative ortho-acylation of O-methyl ketoximes and O-methyl aldoximes with benzylic and aliphatic alcohols from the alcohol oxidation level is described. This protocol potentially provides new opportunities to use readily available alcohols as starting materials for catalytic reactions, and represents a catalytic alternative to transcend the barriers imposed by classical Friedel-Crafts acylation. A highly efficient palladium-catalyzed oxidative ortho-acylation of O-methyl ketoximes and O-methyl aldoximes with benzylic and aliphatic alcohols from the alcohol oxidation level is described. Copyright

Metal-Free 2,2,6,6-tetramethylpiperidin-1-yloxy radical (TEMPO) catalyzed aerobic oxidation of hydroxylamines and alkoxyamines to oximes and oxime ethers

TEMPO-Mediated oxidation of hydroxylamines (=hydroxyamines) and alkoxyamines to the corresponding oxime derivatives is reported (TEMPO=2,2,6,6-tetramethylpiperidin-1-yloxy radical; Scheme 2). These environmentally benign oxidations proceed in good to excellent yields (Table 1). For alkoxyamines, oxidation to the corresponding oxime ethers can be performed by using dioxygen as a terminal oxidant in the presence of 5-10 mol-% of TEMPO or 4-substituted derivatives thereof as a catalyst (Scheme 3 and Table 2). Importantly, benzyl bromides can directly be transformed to oxime ethers via in situ alkoxyamine formation by a nucleophilic substitution followed by TEMPO-mediated oxidation (Scheme 4 and Table 3). Copyright