88229-26-9

Basic information

• Product Name: N-Allyl-4-nitrobenzamide
• Synonyms: N-Allyl-4-nitrobenzamide;4-nitro-N-prop-2-enylbenzamide;4-nitro-N-prop-2-enyl-benzamide
• CAS NO: 88229-26-9
• Molecular Formula: C₁₀H₁₀N₂O₃
• Molecular Weight: 206.2
• Mol File: 88229-26-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Allyl-4-nitrobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Allyl-4-nitrobenzamide(88229-26-9)
• EPA Substance Registry System: N-Allyl-4-nitrobenzamide(88229-26-9)

Safety Data

• Hazardous Substances Data: 88229-26-9(Hazardous Substances Data)

Upstream product

• 62-23-7 4-nitro-benzoic acid 
• 107-11-9 1-amino-2-propene 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 28147-56-0 (p-nitrobenzamido)butyraldehyde 
• 1020192-59-9 (S)-(2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)methanol 
• 1020192-49-7 (R)-(2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)methanol 
• 1344667-71-5 2-allyl-6-methylbenzoic acid 
• 1192720-01-6 5-(bromomethyl)-2-(4-nitrophenyl)oxazole 
• 950692-85-0 N-(2-hydroxypropyl)-4-nitrobenzamide 

Relevant articles and documents

Electrochemical oxidative cyclization of: N -allylcarboxamides: Efficient synthesis of halogenated oxazolines

Herein, we reported an efficient and sustainable intramolecular electrochemical cyclization of N-allylcarboxamides for the synthesis of various halogenated oxazolines. This method was conducted in a simple undivided cell by employing lithium halogen salts

Stereoselective Oxidative Cyclization ofN-Allyl Benzamides to Oxaz(ol)ines

This study presents an enantioselective oxidative cyclization ofN-allyl carboxamides via a chiral triazole-substituted iodoarene catalyst. The method allows the synthesis of highly enantioenriched oxazolines and oxazines, with yields of up to 94% and enantioselectivities of up to 98% ee. Quaternary stereocenters can be constructed and, besidesN-allyl amides, the corresponding thioamides and imideamides are well tolerated as substrates, giving rise to a plethora of chiral 5-memberedN-heterocycles. By applying a multitude of further functionalizations, we finally demonstrate the high value of the observed chiral heterocycles as strategic intermediates for the synthesis of other enantioenriched target structures.

Micellar Catalysis for Sustainable Hydroformylation

It is here reported a fully sustainable and generally applicable protocol for the regioselective hydroformylation of terminal alkenes, using cheap commercially available catalysts and ligands, in mild reaction conditions (70 °C, 9 bar, 40 min). The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in good to high yields. The substrate scope is largely explored as well as the application of hydroformylation in tandem with intramolecular hemiacetalization thus demonstrating the compatibility with a broad variety of functional groups. The reaction is efficient even in large scale and the catalyst and micellar water phase can be reused at least 5 times without any impact in reaction yields. The efficiency and sustainability of this protocol is strictly related to the in situ transformation of the aldehyde into the corresponding Bertagnini's salt that precipitates in the reaction mixture avoiding organic solvent mediated purification steps to obtain the final aldehydes as pure compounds.

Electrochemical Fluorocyclization of N-Allylcarboxamides to 2-Oxazolines by Hypervalent Iodine Mediator

A resource saving protocol for the synthesis of 5-fluoromethyl-2-oxazolines by using electrochemistry has been realized. Thereby, a hypervalent iodine species I(III) is generated by anodic oxidation in the presence of Et3N·5HF and mediates the

Fluorocyclisation via I(I)/I(III) catalysis: A concise route to fluorinated oxazolines

Herein, we describe a catalytic fluorooxygenation of readily accessible N-allylcarboxamides via an I(I)/I(III) manifold to generate 2-oxazolines containing a fluoromethyl group. Catalysis is conditional on the oxidation competence of Selectfluor, whilst HF serves as both a fluoride source and Br?nsted acid activator. The C(sp3)–F bond of the mono-fluoromethyl unit and the C(sp3)–O bond of the ring are aligned in a synclinal relationship thereby engaging in stabilising hyperconjugative interactions with vicinal, electron-rich σ-bonds (σC–C→σ*C–F and σC–H→σ*C–O). This manifestation of the stereoelectronic gauche effect was established by X-ray crystallographic analysis of a representative example. Given the importance of fluorine in drug discovery, its ability to modulate conformation, and the prevalence of the 2-oxazoline scaffold in Nature, this strategy provides a rapid entry into an important bioisostere class.

Efficient conversion of acids and esters to amides and transamidation of primary amides using OSU-6

OSU-6, an MCM-41 type hexagonal mesoporous silica with strong Bronsted acid properties, has been used to promote the high-yield conversion of carboxylic acids and esters to carboxamides as well as transamidations of primary amides in a one-pot solventless approach. A metal-free heterogeneous catalyst that promotes all of these processes has not been previously reported. OSU-6 enables these transformations to proceed in shorter times and at lower temperatures for a broad range of substrates. An added benefit is that the catalyst can be recycled and reused multiple times without significant loss of activity.

Synthesis of cyclopropylpyrrolidines via reaction of N-allyl-N-propargylamides with a molybdenum carbene complex. Effect of substituents and reaction conditions

Previous studies have demonstrated that group 6 carbene complexes react with α,ω-enynes to form vinylcyclopropane derivatives in good to excellent yield, and that the length and composition of the tether between the alkyne and the alkene often has a dramatic impact on the viability of this reaction pathway. The reactivity of allylpropargyl amine derivatives with pentacarbonyl(1-methoxypentylidene)molybdenum(0) (14a) was investigated in order to provide further insight into the steric and electronic factors controlling this reaction. Treatment of allylpropargyl amines with 14a failed to produce the desired cyclization products while treatment of allylpropargyl amides with 14a led to the expected cyclopropylpyrrolidine systems in good to excellent yields. Higher yields are obtained when the reaction is conducted in a sealed vial in the presence of atmospheric oxygen.

The application of a mechanistic model leads to the extension of the sharpless asymmetric dihydroxylation to allylic 4-methoxybenzoates and conformationally related amine and homoallylic alcohol derivatives

The scope and utility of the Sharpless asymmetric dihydroxylation has been expanded to include the use of allylic 4-methoxybenzoates as precursors of a wide variety of substituted chiral glycerol derivatives. The allylic 4-methoxybenzoyl group was found to be superior to other allylic alcohol protecting groups with respect to both yield and enantiomeric purity of the product. For example, asymmetric dihydroxylation of allyl 4-methoxybenzoate (6a) using the (DHQD)2PYDZ·OsO4 (1·OsO4) catalyst system affords (S)-3-(4-methoxybenzoyloxy)-1,2-propanediol (7a) in >99% yield and 98% ee. The 4-methoxybenzoates of a variety of other allylic alcohols also serve as excellent substrates, in contrast to the parent alcohols themselves. The efficient asymmetric dihydroxylation of homoallylic 4-methoxyphenyl ethers (12a and 15), allyl 9-fluorenimine (18b), bis(homoallyl) 4-methoxybenzoate (14) and other structurally related substrates is also described. This methodology was developed under mechanistic guidance from the transition state model advanced earlier by us for the bis-cinchona alkaloid catalyzed asymmetric dihydroxylation reaction. The 4-methoxybenzoyl group functions not only to selectively protect one of the hydroxy groups of the product triol for subsequent synthetic manipulation but also to provide an extended binding group that participates in hydrophobic and aryl-aryl interactions with the U-shaped binding pocket of the (DHQD)2PYDZ·OsO4 catalyst (1·OsO4), thereby enhancing enantioselectivity.

POTENTIAL CENTRAL NERVOUS SYSTEM ACTIVE AGENTS. 3. SYNTHESIS OF SOME SUBSTITUTED BENZAMIDES AND PHENYLACETAMIDES.

The preparation and special properties (IR, **1H NMR) are given for 45 benzamides and 10 phenylacetamides substituted on nitrogen with allyl, benzhydryl, benzyl, or cyclopropyl groups, and variously substituted on the acyl part with halo, methoxyl, methyl, or nitro groups. The benzamide derivatives were synthesized by the Schotten-Baumann method, and the phenylacetamide derivatives were prepared by heating the appropriate N-benzhydrylammonium salt in o-xylene. Thirty-one of the compounds are new.