180324-13-4

Basic information

• Product Name: 2H-1,5-Diazonin-2-one, 1-(3-aminopropyl)octahydro-4-phenyl-, (4S)-
• CAS NO: 180324-13-4
• Molecular Formula: C16H25N3O
• Molecular Weight: 275.394
• Mol File: 180324-13-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2H-1,5-Diazonin-2-one, 1-(3-aminopropyl)octahydro-4-phenyl-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1,5-Diazonin-2-one, 1-(3-aminopropyl)octahydro-4-phenyl-, (4S)-(180324-13-4)
• EPA Substance Registry System: 2H-1,5-Diazonin-2-one, 1-(3-aminopropyl)octahydro-4-phenyl-, (4S)-(180324-13-4)

Safety Data

• Hazardous Substances Data: 180324-13-4(Hazardous Substances Data)

Upstream product

• 112020-24-3 (+)-(2S)-2,6,7,8-tetrahydro-2-phenyl-3H-pyrrolo<1,2-a>pyrimidin-4-one 
• 100-52-7 benzaldehyde 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 163460-81-9 tert-butyl (E)-[(S)-p-tolylsulfinyl]cinnamate 
• 163460-82-0 tert-butyl (E)-[(R)-p-tolylsulfinyl]cinnamate 
• 112020-25-4 (S)-4-phenyl-1,5-diazacyclononan-2-one 
• 76598-25-9 (R)-(+)-1,5-Diaza-4-phenylbicyclo<4.3.0>nonan-2-one 
• 180324-14-5 (S)-4-phenyl-1-(2'-cyanoethyl)-1,5-diazacyclononan-2-one 
• 400782-35-6 (S)-(-)-4-phenyl-1-(3'-phthalimidopropyl)-1,5-diazacyclononan-2-one 

Downstream Products

• 166373-40-6 (-)-(2S)-2-phenyl-1,5,9-triazacyclotridecan-4-one 
• 53938-05-9 (S)-(-)-celacinnine 
• 74133-16-7 (-)-(2S)-9-hydroxy-2-phenyl-1,5,9-triazacyclotridecan-4-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.

95. Asymmetric synthesis of the alkaloids mayfoline and N(1)-Acetyl-N(1)-deoxymayfoline

The total syntheses of the spermidine alkaloids (-)-mayfoline (11) and (+)-N(1)-acetyl-N(1)-deoxymayfoline (12) are described. These macrocyclic lactams belong to the most interesting conjugates of the polyamine derivatives very commonly found in nature. The enantioselective syntheses were achieved through resolution of the methyl 3-amino-3-phenylpropanoate (2) by recrystallization of its (+)-L-tartrate salt. Construction of the 13-membered ring ensued through condensation, reductive ring expansion (internal bond cleavage), and finally a transamidation reaction involving a second ring expansion.