470678-04-7

Basic information

• Product Name: benzyl N-benzyl-N-(1-phenyl-3-butenyl)carbamate
• Synonyms: benzyl N-benzyl-N-(1-phenyl-3-butenyl)carbamate
• CAS NO: 470678-04-7
• Molecular Weight: 371.479
• Mol File: 470678-04-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: benzyl N-benzyl-N-(1-phenyl-3-butenyl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl N-benzyl-N-(1-phenyl-3-butenyl)carbamate(470678-04-7)
• EPA Substance Registry System: benzyl N-benzyl-N-(1-phenyl-3-butenyl)carbamate(470678-04-7)

Safety Data

• Hazardous Substances Data: 470678-04-7(Hazardous Substances Data)

Upstream product

• 620-05-3 iodomethylbenzene 
• 138723-71-4 benzyl (1-phenylbut-3-en-1-yl)carbamate 
• 43008-56-6 Benzoyl-benzyl-carbamic acid benzyl ester 
• 1485-70-7 N-benzylbenzamide 
• 24850-33-7 allyltributylstanane 
• 470677-92-0 benzyl-(phenyl-trimethylsilanyloxy-methyl)-carbamic acid benzyl ester 

Relevant articles and documents

Diastereoselective synthesis of 6-functionalized 4-aryl-1,3-oxazinan-2-ones and their application in the synthesis of 3-aryl-1,3-aminoalcohols and 6-arylpiperidine-2,4-diones

Halocyclocarbamation of benzyl N-(1-phenyl-3-butenyl)carbamates afforded 6-functionalized 4-aryl-1,3-oxazinan-2-ones with moderate to excellent diastereoselectivity depending on the N-substituent. Importantly, in contrast to reported cyclocarbamations of homoallylic carbamates, which are generally trans-diastereoselective, cyclization of N-unsubstituted Cbz-protected homoallylamines led to cis-1,3-oxazinan-2-ones, predominantly. The use of N-benzylated and in situ prepared N-silylated derivatives resulted however in trans-selectivity. Transition states are proposed to explain the stereochemical influence of the N-substituent on the cyclocarbamations. The functionalized 1,3-oxazinan-2-ones could be further elaborated towards biologically or synthetically important 6-arylpiperidine-2,4-diones and 3-aryl-1,3-aminoalcohols.