81590-76-3

Upstream product

• 4883-67-4 2-nitrocyclohexanone 
• 107-02-8 acrolein 
• 1424-22-2 1-cyclohexenyl acetate 
• 108-94-1 cyclohexanone 

Downstream Products

• 1437175-59-1 2-(2-(1,3-dioxolan-2-yl)ethyl)-2-nitrocyclohexanone 
• 1428236-74-1 (S)-2-(2-(1,3-dioxolan-2-yl)ethyl)-2-nitrocyclohexanone 
• 95299-32-4 3-(1'-nitro-2'-oxocyclohexyl)propionic acid 
• 95299-33-5 5-(2',3',4',5'-Tetrahydro-2'-nitro-5'-oxo-2'-furyl)pentansaeure 
• 84246-77-5 2-(3-Hydroxypropyl)-2-nitrocyclohexanone 
• 2568-20-9 2-(3-oxopropyl)cyclohexanone 
• 71759-57-4 4-oxononanedioic acid 
• 92643-60-2 2-(3-Hydroxy-butyl)-2-nitro-cyclohexanone 
• 81590-77-4 2-Methyl-4a-nitro-octahydro-chromen-8a-ol 

Relevant academic research and scientific papers

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

Organocatalytic enantioselective conjugate addition of 2-nitrocyclohexanone to acrylaldehyde: A concise two-step synthesis of chiral building block 1-azaspiro[4.5]decan-6-one

A gram-scale organocatalytic enantioselective Michael addition of a-nitrocyclohexanone to acrolein has been developed, and it was successfully applied to a concise two-step synthesis of (1S)-azaspiro[4.5] decan-6-one, a useful chiral building block for th

Practical and User-Friendly Procedure for Michael Reactions of α-Nitroketones in Water

A variety of α,β-unsaturated carbonyl derivatives gave selective Michael additions with several α-nitrocycloalkanones in water, at room temperature without any added catalyst, or in very dilute, aqueous solutions of potassium carbonate. Both preparative methods constitute new, environmentally benign and more efficient alternatives to previous procedures.

A Novel NO2/OH Exchange in α-Nitro Ketones: A Mechanistic Investigation

The reaction of α-nitro ketones to the corresponding α-hydroxy ketones under basic aqueous conditions, a novel transformation, was studied. The investigation revealed that the reaction is only possible with α-nitro ketones that are CH-acidic in the α′-position and readily deprotonated under the reaction conditions. The NO2/OH exchange was established to proceed with retention of configuration at the stereogenic center, and labeling experiments have shown that the OH O-atom originates, to a great extent, from the solvent. In particular, the stereochemical course of the reaction and the incorporation of external nucleophiles led us to propose a mechanism that involves neighboring-group participation. The product formation is explained by a double SN2 reaction, which proceeds via a favorsii-like cyclopropanone intermediate.

Conjugate Addition of Nitro-Derivatives to α,β-Unsaturated Carbonyl Compounds on Basic Alumina

Conjugate addition of nitroalkanes to α,β-unsaturated carbonyl compounds occurs in the presence of basic alumina without a solvent.Yields are fair to good also with substrates which are acid or base sensitive.

A New Synthesis of 1,5-Dicarbonyl Compounds under Neutral Conditions

Michael addition of α-nitroketones to methyl vinyl ketone or acrylaldehyde followed by denitration with Bu3SnH affords 1,5-dicarbonyl compounds in good yields.

A NEW SYNTHESIS OF MACROCYCLIC KETO-LACTONES VIA RING EXPANSION OF 2-(3-HYDROXYPROPYL)-2-NITROCYCLOALKANONES

2-(3-Hydroxypropyl)-2-nitrocycloalkanones undergo base-catalysed isomerisation into nitro-lactones containing four more atoms in the ring, which can be smoothly converted to the corresponding keto-lactones.

Synthesis of Macrocyclic Lactones by Ring Enlargement Reaction

Treatment of 3-(1-nitro-2-oxocyclohexyl)propanal (1) prepared by Michael addition of 2-nitrocyclohexanon and acrylaldehyde with methyltri(2-propoxy)titanium yielded a mixture of 2 and 3 which was converted into 6-nitro-9-decanolide (4).