31887-88-4

Upstream product

• 583-60-8 2-Methylcyclohexanone 
• 100-46-9 benzylamine 
• 62-53-3 aniline 

Downstream Products

• 57152-94-0 (E)-N-benzylcinnamamide 
• 31777-08-9 N-Benzyl-N-cinnamoyl-1-amino-2-methyl-cyclohexen 
• 100699-38-5 2-methyl-2-(2-(phenylsulfonyl)ethyl)cyclohexanone 
• 77508-43-1 C₉H₁₈⁽²⁾HClSi 
• 77508-45-3 C₉H₁₈⁽²⁾HClSi 
• 80344-57-6 cis-N-benzyl-2-methylcyclohexylamine 
• 80344-57-6 trans-N-benzyl-2-methylcyclohexylamine 
• 76947-32-5 N-Benzyl-N-(6-methyl-cyclohex-1-enyl)-acetamide 
• 76947-31-4 N-Benzyl-N-(2-methyl-cyclohex-1-enyl)-acetamide 
• 94089-47-1 3-(1-methyl-2-oxocyclohexyl)propionic acid methyl ester 

Relevant academic research and scientific papers

Diastereoselectivity in the Michael-Type Addition of Imines Reacting as Their Secondary Enamine Tautomers

Michael-type reactions of 2-methyl(benzylimino)cyclohexane (reacting as its secondary enamine tautomer 1) were performed with methyl methacrylate (2), methyl crotonate (5), and maleic anhydride (7).In each case, the stereochemical relationship of the substituents in the major cyclized adducts 4, 6, and 8 obtained with excellent diastereoselectivities was shown to be the one predicted in a previous theoretical calculation which established that the complex of the reactants has a chairlike geometry.The predicted concomitant H-transfer and C-C bond formation in these reaction was also confirmed in the methyl methacrylate case.Besides, these experiments have shown that regioisomers are formed in appreciable amounts when substituted electrophilic olefins are used.

Extension of the Nenitzescu reaction to simple ketones provides an efficient route to 1′-alkyi-5′-hydroxynaltrindole analogues, potent and selective δ-opioid receptor antagonists

The well-established Nenitzescu reaction of imines of β-dicarbonyl systems, as their enamine tautomers, with benzoquinone has been applied to a wide range of such imines to give 5-hydroxyindoles, some of which are of significant biological importance. Thi

Regioselective photochemical rearrangement of N-mesyloxylactams

N-Mesyloxylactams can undergo ring contraction either by C-3 (usually observed) or C-5 migration. C-5 migration can occur when the C-3 migration product possesses ring strain, but it does not usually compete with C-3 migration. The greater preference for C-3 migration is due to the carbonyl oxygen atom, which greatly stabilizes the intermediate. Studies of the photochemical rearrangement of N-mesyloxylactams showed that the lone pair of the carbonyl oxygen atom, and not the degree of the substitution atthe migrating carbon atoms, is the governing factor in the regioselectivity of the reaction. Copyright

Photochemical rearrangement of N-mesyloxylactams: Stereospecific formation of N-heterocycles

N-Mesyloxylactams undergo an efficient ring-contraction to N-heterocycles of various ring sizes. Yields increase with the degree of substitution α to the carbonyl. The stereochemical information of a chiral migrating carbon is conserved making this reacti

New insights into NIS-promoted aminocyclization. Synthesis of decahydroquinolines from 2-allylcyclohexylamines

Equation Presented Bishomoallylic secondary amines embodying the 2-allyl-N-benzylcyclohexylamine unit react with NIS to undergo cyclization through 6-endo processes in either the cis or trans series. Nevertheless, when the resulting cis-3-iododecahydroqui

BF3-mediated additions of organolithiums to ketimines: X-ray crystal structures of BF3-ketimine complexes

(Chemical Equation Presented) Additions of lithium acetylides and n-BuLi to N-alkyl ketimines mediated by BF3-Et2O in THF afford hindered tert-alkylamines in moderate to good yields. Stereochemical results and crystal structures of t

Reaction of Cyclohexanones Imines with Substituted Nitroolefins. New Synthesis of Tetrahydroindole Derivatives

The Michael-type addition of cyclohexanones imines, reacting as their secondary enamine tautomers, to β-substituted nitroolefins is followed by a cyclization reaction with elimination of the nitro group to afford substituted tetrahydroindoles. When a 2-methylcyclohexanone imine is reacted, an unexpected inversion of the regioselectivity is observed when compared with β-substituted ethylenic esters, thus allowing to obtain also substituted tetrahydroindoles. - Keywords: Imines; Michael reactions; Regioselection; Indoles

β- and γ-lactams by nickel powder mediated 4-exo or 5-endo radical cyclisations. A concise construction of the mesembrine skeleton

N-Alkenyl trichloroacetamides, upon treatment with nickel powder and acetic acid in refluxing 2-propanol undergo reversible 4-exo radical cyclisation. The cyclised radical can be trapped in different ways leading to β-lactams. When the trap is omitted or not efficient enough, unusual irreversible 5-endo cyclisation occurs affording functionalised five-membered lactams. Synthesis of bicyclic γ-lactams has also been examined providing in few steps an access to the Sceletium alkaloids skeleton.

Stereoselective Reductions of Substituted Cyclohexyl and Cyclopentyl Carbon-Nitrogen ? Systems with Hydride Reagents

Reductions of 3- and 4-substituted cyclohexyl imines, iminium salts, and enamines (via iminium ions) with various hydride reagents reveal that while small reagents (NaBH4, NaBH3CN) favor axial approach as observed with the corresponding ketones, even moderately bulky reagents (i.e., acetoxyboranes) attack preferentially from the equatorial side.This is in direct contrast to the results observed for the same reagents with the corresponding ketones and is interpreted as implying that additional steric interactions induced by the nitrogen substituents encumber axial attack by substituted hydride reagents and force approach from the equatorial direction.The very bulky tri-sec-butylborohydride anion affords highly stereodiscriminating equatorial attack.Reductions of 2-alkylcyclohexyl and 2-alkylcyclopentyl imines and enamines also proceed with high stereoselectivity to give cis-2-alkyl cyclic amines with both hindered and unhindered reagents.This is interpreted to be the result of (1) augmented steric interactions between nitrogen substituents and equatorial 2-alkyl groups (1,3-allylic strain) which induces conformational changes to favor the axial 2-alkyl conformer and (2) hindrance toward equatorial approach by reagents induced by axial alkyl substituents.The result is that equatorial approach is favored with equatorial 2-alkyl conformers and preferential axial approach with axial 2-alkyl conformers, leading to stereoselective production of cis-2-alkylamines. trans-2-n-Propyl-4-tert-butylcyclohexanone is reduced by LiBH(sec-Bu)3 preferentially from the axial direction in contrast to the usual highly selective equatorial attack observed with other cyclohexanones.