176847-60-2

Basic information

• Product Name: 4(3H)-Quinazolinone, 2-[(1S)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-[(2S,3S)-2-phenyl -3-(trimethylsilyl)-1-aziridinyl]-
• CAS NO: 176847-60-2
• Molecular Formula: C27H39N3O2Si2
• Molecular Weight: 493.797
• Mol File: 176847-60-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4(3H)-Quinazolinone, 2-[(1S)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-[(2S,3S)-2-phenyl -3-(trimethylsilyl)-1-aziridinyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(3H)-Quinazolinone, 2-[(1S)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-[(2S,3S)-2-phenyl -3-(trimethylsilyl)-1-aziridinyl]-(176847-60-2)
• EPA Substance Registry System: 4(3H)-Quinazolinone, 2-[(1S)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-[(2S,3S)-2-phenyl -3-(trimethylsilyl)-1-aziridinyl]-(176847-60-2)

Safety Data

• Hazardous Substances Data: 176847-60-2(Hazardous Substances Data)

Upstream product

• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 175085-31-1 (S)-3-acetoxyamino-2-[1-(t-butyldimethylsilyloxy)ethyl]quinazolin-4(3H)-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 141236-01-3 (S)-3-Amino-2-(1-hydroxyethyl)-3,4-dihydroquinazolin-4-one 
• 175085-35-5 3-amino-2-<(1S)-1-tert-butyldimethylsilyloxyethyl>-3,4-dihydroquinazolin-4-one 

Downstream Products

• 177018-15-4 (2R,3S)-2-cyano-3-phenylaziridine 
• 159517-27-8 (R)-2-amino-3-phenylpropanenitrile 
• 181376-74-9 (+)-(R)-N-(1-cyano-2-phenyl-ethyl)-acetamide 

Relevant articles and documents

Preparation of N-H aziridines in high enantiomeric excess by in situ aziridine-azirine-aziridine interconversion

Aziridine 6 is produced highly diastereoselectively by treatment of enantiopure 3-acetoxyaminoquinazolinone 4 (Q*NHOAc) with β-trimethylsilylstyrene: desilylative elimination of Q* and in situ addition of cyanide to the intermediate azirine gives the NH-a

Reagent-controlled diastereoselectivity in aziridination of alkenes by chiral 3-acetoxyamino-3,4-dihydroquinazolin-4-ones: 1'-(t- butyldimethylsilyloxy)ethyl as the chiral 2-substituent on the quinazolinone

Conformational preferences within the (t)BuMe2SiOCH(Me)C=N unit in 3- acetoxyaminoquinazolinone 3 lead to well defined site preferences for H, Me and OSiMe21Bu in the transition state for, and hence high diastereoselectivity in, its reaction with β-trimethylsilylstyrene 4 to give aziridine 5.