66050-07-5

Upstream product

• 66050-05-3 N,9-dibenzyl-8-azabicyclo<4.3.0>non-1(6)-en-7-one 
• 100835-75-4 (3R,3aS)-2,3-Dibenzyl-2,3,3a,4,7,7a-hexahydro-isoindol-1-one 
• 85738-13-2 (E)-Penta-2,4-dienoic acid benzyl-(1-benzyl-allyl)-amide 
• 52126-35-9 trans 2,4-pentadienoyl chloride 
• 66090-85-5 N-benzyl-9-benzylidene-cis-8-azabicyclo<4.3.0>nonan-7-one 
• 100835-75-4 (1RS,6SR,9RS)-N,9-dibenzyl-8-azabicyclo<4.3.0>non-3-en-7-one 
• 66056-99-3 N-benzyl-9-benzylidene-8-azabicyclo<4.3.0>non-3-en-7-one 
• 85738-06-3 N-(1-benzylprop-2-ynyl)benzylamine 
• 85738-08-5 N-(1-benzylprop-2-enyl)benzylamine 
• 135663-97-7 1-phenylbut-3-yn-2-ol 
• 85738-05-2 1-phenylbut-3-yn-2-yl 4-methylbenzenesulfonate 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 66050-08-6 (1RS,6SR,9RS)-9-benzyl-8-azabicyclo<4.3.0>nonan-7-one 

Relevant academic research and scientific papers

The Reduction of Tertiary N-Styrylenamides

Magnesium and methanol reduction of N,9-dibenzyl-8-azabicyclonon-1(6)-en-7-one (6) gave all four racemates of N,9-dibenzyl-8-azabicyclononan-7-one (1)-(4), with a 13:6 ratio of cis-fused to trans-fused products.Selective reduction of N,9-dibenzyl-8-azabicyclonon-1(6),3-dien-7-one (5) gave almost exclusively the two cis-fused racemates of N,9-dibenzyl-8-azabicyclonon-3-en-7-one (9) and (10).Magnesium and methanol did not reduce (E)-N-benzyl-9-benzylidene-cis-bicyclononan-7-one (7) and (E)-N-benzyl-N-(1-methyl-2-phenylvinyl)-acetamide (16a), but did reduce (E)-N-benzyl-N-styrylacetamide (16b) and (E)- and (Z)-N-styrylpyrrolidin-2-one (13) and (14); incomplete reduction of (Z)-N-benzyl-N-(1-methyl-2-phenylvinyl)-acetamide (15a) and (Z)-N-benzyl-N-styrylacetamide (15b) was observed.Reduction does not occur when the styryl phenyl group is twisted out of conjugation.Sodium and liquid ammonia reduction of (E)-N-benzyl-9-benzylidene-cis-8-azabicyclononan-7-one (7) gave (1RS,6SR,9RS)-9-benzyl-8-azabicyclononan-7-one and N-benzyl-2-(2-phenylethyl)cyclohexane-1-carboxamide (20).A similar cleavage of the β-styryl-nitrogen bond was observed in the reduction of (Z)-N-benzyl-N-(1-methyl-2-phenylvinyl)acetamide (15a), but not with (E)-N-styrylpyrrolidin-2-one (13).Several tertiary N-styrylenamides were not reduced by sodium cyanoborohydride in acetic acid but N-benzyl-9-benzylidene-cis-8-azabicyclonon-3-en-7-one (8) and N-benzyl-9-benzylidene-cis-8-azabicyclononan-7-one (7) gave (1RS,6SR,9RS)-N,9-dibenzyl-8-azabicyclonon-3-en-7-one (9) and (1RS,6SR,9RS)-N,9-dibenzyl-8-azabicyclononan-7-one (2) respectively.

The Synthesis of 9-Substituted N-Benzyl-8-azabicyclonon-4-en-7-ones by the Intramolecular Diels-Alder Reaction

The intramolecular thermal cyclisation of N-allyl-N-benzylpenta-2(E),4-dienamide in refluxing NN-dimethylformamide gives N-benzyl-cis- and trans-8-azabicyclonon-4-en-7-one; N-allyl-N-benzylhexa-2(E),4(E)-dienamide gives (1RS, 3RS, 6SR)-3-methyl- an