77184-12-4

Basic information

• Product Name: 2-Azetidinone, 3-hydroxy-1-methyl-3-phenyl-
• CAS NO: 77184-12-4
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Mol File: 77184-12-4.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 3-hydroxy-1-methyl-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 3-hydroxy-1-methyl-3-phenyl-(77184-12-4)
• EPA Substance Registry System: 2-Azetidinone, 3-hydroxy-1-methyl-3-phenyl-(77184-12-4)

Safety Data

• Hazardous Substances Data: 77184-12-4(Hazardous Substances Data)

Upstream product

• 164594-44-9 N-methyl-3-hydroxy-3-phenylazetidine-2-thione 
• 77184-09-9 N-(β-Hydroxyphenaethyl)-N-methyl-carbaminsaeure-(t-butyl)ester 
• 77184-10-2 1,1-dimethylethyl methyl(2-phenyl-2-oxoethyl)carbamate 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 73286-37-0 N-(2-oxo-2-phenylethyl)formamide 
• 93-58-3 benzoic acid methyl ester 
• 671777-78-9 N-methyl-2-oxo-2-phenyl-N-trimethylsilanylmethyl-acetamide 
• 51579-87-4 N,N-dimethyl-2-oxo-2-phenylacetamide 
• 76467-28-2 N-Methyl-N-phenacylformamid 
• 143168-28-9 [(2S,3S)-3-(Hydroxy-diphenyl-methyl)-1,4-dioxa-spiro[4.5]dec-2-yl]-diphenyl-methanol; compound with N,N-dimethyl-2-oxo-2-phenyl-acetamide 
• 143168-27-8 [(2S,3S)-3-(Hydroxy-diphenyl-methyl)-1,4-dioxa-spiro[4.4]non-2-yl]-diphenyl-methanol; compound with N,N-dimethyl-2-oxo-2-phenyl-acetamide 
• 68579-60-2 2-(methylamino)-1-phenylethanol 

Downstream Products

• 184833-02-1 Methanesulfonic acid 1-methyl-2-oxo-3-phenyl-azetidin-3-yl ester 

Relevant articles and documents

Hydroxy-β-thiolactams to oxazole-2-thiones. A novel dmso-promoted oxidation

(Chemical Equation Presented) 3-Aryl-3-hydroxy-1-methylazetidine-2-thiones react with HCI in DMSO to give 3-methyl-5-aryloxazole-2-thiones. Substituent effects correlate with rate effects on hydrolyses of acetals of benzaldehyde. An 17O labeling experiment indicates that the oxygen atom of the product is derived from the hydroxyl group. Trifluoroacetic anhydride/DMSO in CH2Cl2 can also promote the reaction. Mechanisms involving a Grob-type fragmentation of an activated substrate, followed by recyclization, or a cyclopropylcarbinyl type of rearrangement can account for this oxidative rearrangement.

β-Lactam-Forming Photochemical Reactions of N-Trimethylsilylmethyl- and N-Tributylstannylmethyl-Substituted α-Ketoamides

Two mechanisms have been proposed for the β-lactam-forming photochemical reactions of α-ketoamides. One, suggested by Aoyama, involves excited-state H-atom abstraction while the other, put forth by Whitten, follows a sequential SET-proton-transfer route. The photochemical properties of N-trimethylsilylmethyl- and N-tributylstannylmethyl-substituted α-ketoamides were explored in order to gain information about the mechanism of this process and to develop a regioselective method for β-lactam formation. The results of this effort show that (1) photoreactions of N-trimethyl-silylmethyl-substituted α-ketoamides proceed by competitive H-atom abstraction and sequential SET-desilylation pathways and (2) a sequential SET-destannylation pathway is preferentially followed in photochemical reactions of the tributylstannylmethyl-substituted α-ketoamides.

Enantioselective photoreaction in inclusion crystal

Mixing of powdered chiral hosts and achiral guest compounds gives inclusion complexes in which the latter molecules are arranged in a chiral form. Freezing of the chirality of the guest compounds by photoirradiation in the solid state gives optically active photoreaction products.