1042368-71-7

Basic information

• Product Name: C₂₆H₂₇NO
• Synonyms: C₂₆H₂₇NO
• CAS NO: 1042368-71-7
• Molecular Weight: 369.506
• Mol File: 1042368-71-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₆H₂₇NO(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₆H₂₇NO(1042368-71-7)
• EPA Substance Registry System: C₂₆H₂₇NO(1042368-71-7)

Safety Data

• Hazardous Substances Data: 1042368-71-7(Hazardous Substances Data)

Upstream product

• 1283098-16-7 (7aR,10R,12S)-7a,8,9,10-tetrahydro-10-ethynyl-12-phenyl-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine 
• 1283098-11-2 (7aR,10R,12S)-7a,8,9,10-tetrahydro-10-vinyl-12-phenyl-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine 
• 1730-25-2 allylmagnesium bromide 
• 667870-41-9 (7aR,10R,12S)-10-(1H-benzotriazol-1-yl)-7a,8,9,10-tetrahydro-12-phenyl-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine 

Downstream Products

• 1283098-14-5 (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester 
• 172277-49-5 (1R,5S)-2-acetyl-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>-2-octene 
• 50-36-2 Cocaine 

Relevant articles and documents

Total synthesis of (-)-cocaine and (-)-ferruginine

Total synthesis of tropane alkaloids (-)-cocaine and (-)-ferruginine were accomplished in nine steps each and in 55% and 46% overall yields, respectively, starting from the known Betti base derivative (+)-(7aR,10R,12S)-10-(1H- benzotriazol-1-yl)-7a,8,9,10-tetrahydro-12-phenyl-12H-naphtho[1,2-e]pyrrolo[2, 1-b][1,3]oxazine. In this novel route, RCM reaction and 1,3-dipolar cycloaddition were employed as key steps for the enantioselective construction of tropane skeleton and the regioselective introduction of 3-bromo-2-isoxazoline ring as masked cis-2,3-disubstituents. To obtain the desired precursor (2S,5R)-2-allyl-5-vinylpyrrolidine for RCM reaction, we developed a general and practical method for the preparation of enantiopure cis-2,5-disubstituted pyrrolidines bearing alkene- and/or alkyne-containing substituents. We also offered two highly efficient pathways for the conversion of the 3-bromo-2-isoxazoline ring into the desired cis-2,3-disubstituted groups in (-)-cocaine and (-)-ferruginine.