76465-85-5

Basic information

• Product Name: (+/-)-dihydroperiphylline
• Synonyms: (+/-)-dihydroperiphylline
• CAS NO: 76465-85-5
• Molecular Weight: 405.54
• Mol File: 76465-85-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (+/-)-dihydroperiphylline(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-dihydroperiphylline(76465-85-5)
• EPA Substance Registry System: (+/-)-dihydroperiphylline(76465-85-5)

Safety Data

• Hazardous Substances Data: 76465-85-5(Hazardous Substances Data)

Upstream product

• 88909-10-8 (R,S)-4-phenyl-1,5-diazacyclooctan-2-one 
• 76405-00-0 5-[(E)-(3-Phenyl-acryloyl)]-[1,5]diazonan-2-one 
• 76405-01-1 7-oxo-1,6-diazabicyclo<4.3.0>nonane 
• 76405-02-2 [1,5]Diazonan-2-one 
• 76404-99-4 (E)-1-((E)-4-Methoxy-2,3,6,7,8,9-hexahydro-[1,5]diazonin-1-yl)-3-phenyl-propenone 
• 11082-66-9 periphylline 
• 110425-69-9 4-phenyl-1,5,9-triazacyclotridecan-2-one 
• 102-92-1 Cinnamoyl chloride 
• 76404-98-3 (E)-2-phenyl-9-(3-phenylacryloyl)-2,5,6,7,8,9,10,11-octahydro-3H-1,4a,9-triazabenzocyclononen-4-one 
• 110447-23-9 1-(4-chlorobutyl)-4-phenyl-1,5-diazacyclooctan-2-one 
• 110425-68-8 1-(4-aminobutyl)-4-phenyl-1,5-diazacyclooctan-2-one 
• 154218-88-9 N-(3-bromopropyl)-4-phenylazetidin-2-one 
• 88909-09-5 N-(3-chloropropyl)-4-phenylazetidin-2-one 
• 52341-70-5 N-chlorosulfonyl-4-phenylazetidin-2-one 

Downstream Products

• 64482-04-8 tetrahydroperiphylline 

Relevant articles and documents

β-lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids

Syntheses of the macrocyclic spermidine alkaloids (±)-celacinnine (1) and (±)-dihydroperiphylline (2) as well as the related spermine alkaloid (±)-verbascenine (3) were accomplished by means of sequential ring expansions of smaller lactam rings. Three ring expansion methods were employed: (1) transamidation of N-(aminoalkyl)lactams, (2) β-lactam-lactim ether condensation followed by reductive cleavage of the bicyclic 4-oxotetrahydropyrimidine product with NaBH3CN/AcOH and (3) bicyclic acyl hydrazine formation followed by N-N bond cleavage with Na/NH3. Each synthesis features ring expansion of a 4-phenylazetidin-2-one intermediate that undergoes transamidative ring expansion or lactim ether condensation.

Transamidation reactions of β-lactams: A synthesis of (±)-dihydroperiphylline

-

Total synthesis of (±)-dihydroperiphylline

-