268541-14-6

Basic information

• Product Name: Benzamide, 4-methoxy-N-(1-methyl-1-phenylethyl)-N-(phenylmethyl)-
• CAS NO: 268541-14-6
• Molecular Formula: C24H25NO2
• Molecular Weight: 359.468
• Mol File: 268541-14-6.mol

Chemical Properties

• CAS DataBase Reference: Benzamide, 4-methoxy-N-(1-methyl-1-phenylethyl)-N-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, 4-methoxy-N-(1-methyl-1-phenylethyl)-N-(phenylmethyl)-(268541-14-6)
• EPA Substance Registry System: Benzamide, 4-methoxy-N-(1-methyl-1-phenylethyl)-N-(phenylmethyl)-(268541-14-6)

Safety Data

• Hazardous Substances Data: 268541-14-6(Hazardous Substances Data)

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 585-32-0 2-phenyl-2-propylamine 
• 100-39-0 benzyl bromide 
• 454479-63-1 N-(1-methyl-1-phenylethyl)-4-methoxybenzamide 

Downstream Products

• 414871-53-7 (3S,3aS,7aR)-2-(1-methyl-1-phenylethyl)-3-phenyl-2,3,3a,7a-tetrahydro-1H-isoindole-1,5(4H)-dione 
• 848476-42-6 3-((3R,3aR,7R,7aS)-octahydro-1,5-dioxo-3-phenyl-1H-isoindol-7-yl)propyl formate 
• 848476-33-5 (1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate 
• 848476-32-4 (3R,3aR,7R,7aS)-hexahydro-7-(1-triisopropylsilyloxy)propyl-3-phenyl-2-(2-phenylpropan-2-yl)-6H-isoindole-1,5-dione 
• 454479-66-4 (1S,3aR,4S,7aS)-4-methyl-3,6-dioxo-1-phenyl-octahydro-isoindole-2-carboxylic acid tert-butyl ester 
• 454479-65-3 (3S,3aS,7S,7aR)-7-methyl-3-phenylperhydro-isoindole-1,5-dione 

Relevant articles and documents

The synthesis of (-)-isodomoic acid C

The neuroactive algal metabolite (-)-isodomoic acid C, a kainoid amino acid, has been synthesized for the first time. Asymmetric dearomatizing cyclization of an aromatic amide using a chiral lithium amide base generates a bicyclic enone containing a pyrro

Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

Chiral lithium amide bases are able to deprotonate N-benzyl-N-cumyl anisamides enantioselectively to yield enantiomerically enriched benzylic organolithiums. These spontaneously undergo dearomatising cyclisation to yield, in high enantiomeric excess enantiomerically enriched partially saturated isoindolones, which in some cases may be recrystallised to enantiomeric purity. These isoindolone derivatives are converted in nine steps, among them a surprisingly regioselective Baeyer-Villiger reaction, to (-)-kainic acid.

Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

N-Benzyl p-anisamide 6, on lithiation with Bu(t)Li in the presence of HMPA, undergoes a stereoselective anionic cyclisation with loss of aromaticity to give a bicyclic enone which may be converted in nine steps to (±)-kainic acid.