16507-00-9

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 21, p. 107, 1956 DOI: 10.1021/jo01107a023

Upstream product

• 79-46-9 2-nitropropane 
• 107-13-1 acrylonitrile 
• 552-89-6 2-nitro-benzaldehyde 
• 112-02-7 cetyltrimethylammonium chloride 

Downstream Products

• 5165-28-6 5,5-dimethyl-2-pyrrolidone 
• 32827-16-0 4-methyl-4-nitropentanoic acid 
• 34211-69-3 2-amino-5,5-dimethylpyrroline 1-oxide 
• 3123-97-5 dihydro-5,5-dimethyl-2(3H)-furanone 
• 105090-82-2 (4-Amino-4-methyl-pentyl)-carbamic acid tert-butyl ester 
• 542-54-1 isocapronitrile 

Relevant academic research and scientific papers

Intermolecular domino Michael/aldol reactions of α,β-unsaturated esters, aromatic aldehydes, and various nucleophiles promoted with a catalytic amount of a guanidine base in DMSO

In DMSO, a catalytic amount of Barton's base (2-t-butyl-1,1,3,3-tetramethylguanidine, BTMG) effectively catalyzed intermolecular three-component reactions of α,β-unsaturated esters, aldehydes, and carbon-, sulfur-, or nitrogen-pronucleophiles to give three-component addition products with the formation of two new σ-bonds: pronucleophiles and aldehydes reacted with α,β-unsaturated esters at their β-positions and α-positions, respectively. Mechanism studies suggested that these reactions proceeded by the first intermolecular Michael addition of anionic nucleophiles that were formed from pronucleophiles with a catalytic amount of BTMG, followed by intermolecular aldol reactions of transient ester enolates even in the presence of more than stoichiometric amounts of acidic pronucleophiles. High nucleophilicity over Br?nsted basicity of transient enolates in polar solvents was observed for transient ester enolates rather than ketone enolates.

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.

2-Substituted nitrones and isomeric hydroxylamines - obtained via aluminium amalgam reduction of nitro nitriles and ketones-a new access to convenient intermediates for nitroso carbonyl compounds preparation

Substituted five-membered cyclic nitrones (pyrroline N-oxides) have been obtained in good to high yields from tertiary γ-nitro ketones and nitriles employing aluminium amalgam as a reducing agent in moist diethyl ether or THF. Attempts to obtain cyclic amino nitrones from α- or β-nitro nitriles failed and only the corresponding hydroxylamines have been isolated. Both nitrones and hydroxylamines have been used for synthesis of tertiary C-nitroso nitriles or ketones.

Method for producing lysine derivative

The present invention provides a method for industrially producing an optically active lysine derivative useful as a pharmaceutical intermediate. More particularly, the present invention provides a production method including protecting an amino group or an amino group and carboxyl group of optically active 2-amino-6-methyl-6-nitroheptanoic acid with a protecting group, reducing a nitro group to synthesize a 6,6-dimethyl lysine derivative and reacting the 6,6-dimethyl lysine derivative with an acetic acid derivative.

Conjugated addition reactions of nitroalkanes with electrophilic alkenes in aqueous media

The Michael reaction of various nitroalkanes 1 with electrophilic alkenes 2 can be performed in NaOH (0.025-0.1 M), without any organic solvent. In many cases the presence of cetyltrimethylammonium chloride (CTACI), as cationic surfactant, produces better

UTILISATION DE MEMBRANES ECHANGEUSES D'IONS EN ELECTROSYNTHESE ORGANIQUE.

The addition of carbon acids to acrylonitrile or methyl acrylate can be initiated by means of bases electrogenerated in aprotic media in the absence of supporting-electrolyte, at the interface between a porous cathode and a solid polymer electrolyte.The consumption of electricity is below 1E-2 faraday per mole.Putting to the test donors with decreasing acidity (2-nitropropane, malononitrile, diethyl malonate, ethyl cyanacetate, 2-methylcyclohexanone, fluorene) allows to estimate the basicity level that can be reached at such an interface.The influence of differentfactors (such as the nature of the ion exchange membrane, the basicity of the second side of the membrane, the presence of a probase) on the rates and yields of the reactions has been investigated.