131226-02-3

Basic information

• Product Name: 3-phenyl-2-(toluene-4-sulfinyl)-hexahydro-pyrazolo[1,2-a]pyridazin-1-one
• CAS NO: 131226-02-3
• Molecular Weight: 354.473
• Mol File: 131226-02-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-phenyl-2-(toluene-4-sulfinyl)-hexahydro-pyrazolo[1,2-a]pyridazin-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-2-(toluene-4-sulfinyl)-hexahydro-pyrazolo[1,2-a]pyridazin-1-one(131226-02-3)
• EPA Substance Registry System: 3-phenyl-2-(toluene-4-sulfinyl)-hexahydro-pyrazolo[1,2-a]pyridazin-1-one(131226-02-3)

Safety Data

• Hazardous Substances Data: 131226-02-3(Hazardous Substances Data)

Upstream product

• 400782-30-1 t-butyl (-)-3-hydroxy-3-phenyl-2-<(S)-p-tolylsulfinyl>propionate 
• 94404-20-3 (-)-(S_S)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester 
• 100-52-7 benzaldehyde 
• 41103-85-9 (E)-(R)-(+)-β-styryl p-tolyl sulfoxide 
• 505-19-1 piperidazine 
• 131226-01-2 (E)-(R)-1-(Methoxycarbonyl)-2-phenylvinyl p-tolyl sulfoxide 
• 131226-00-1 (E)-(S)-1-(Methoxycarbonyl)-2-phenylvinyl p-tolyl sulfoxide 

Downstream Products

• 76598-25-9 (R)-(+)-1,5-Diaza-4-phenylbicyclo<4.3.0>nonan-2-one 
• 76598-25-9 (S)-(-)-1,5-Diaza-4-phenylbicyclo<4.3.0>nonan-2-one 
• 112020-27-6 (R)-4-phenyl-1,5-diazacyclononan-2-one 
• 112020-25-4 (S)-4-phenyl-1,5-diazacyclononan-2-one 

Relevant articles and documents

Conjugate addition of 6-membered hydrazine to chiral tert-butyl (E)-2-(p-tolylsulfinyl)cinnamates. Synthesis of (S)-celacinnine

Two enantiomers of the bicyclic lactam, (S)- and (R)-9-phenyl-1,6-diazabicyclo[4.3.0]nonan-7-one (6), were synthesized stereoselectively with high optical purity (95% ee) by the asymmetric conjugate addition-cyclization of piperidazine to chiral vinyl sulfoxides, tert-butyl (E)-2-[(R)- and (S)-p-tolylsulfinyl]cinnamate (4), followed by removal of the p-tolylsulfinyl group with SmI2. The subsequent reductive cleavage of the N-N bond of the bicyclic lactam 6 with sodium in liquid ammonia produced the corresponding 9-membered azalactam, (S)- and (R)-4-phenyl-1,5-diazacyclononan-2-one (7) with 99% and 97% ee, respectively. X-ray crystallography showed that (S)-7 exists exclusively as a trans conformer in the crystal state. Starting from (S)-7, naturally occurring (S)-celacinnine 1 was synthesized with 99% ee employing the ring-expansion reaction via intramolecular transamidation.