64468-50-4

Basic information

• Product Name: cis-3-hydroxy-1,4-diphenylazetidin-2-one
• CAS NO: 64468-50-4
• Molecular Weight: 239.274
• Mol File: 64468-50-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: cis-3-hydroxy-1,4-diphenylazetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: cis-3-hydroxy-1,4-diphenylazetidin-2-one(64468-50-4)
• EPA Substance Registry System: cis-3-hydroxy-1,4-diphenylazetidin-2-one(64468-50-4)

Safety Data

• Hazardous Substances Data: 64468-50-4(Hazardous Substances Data)

Upstream product

• 538-51-2 benzylidene phenylamine 
• 94673-73-1 3-acetoxy-1,4-diphenylazetidin-2-one 
• 41625-51-8 trimethylsiloxyacetic acid 
• 33993-35-0 cis-benzylideneaniline 
• 64468-50-4 trans-3-hydroxy-1,4-diphenyl-2-azetidinone 

Downstream Products

• 1379469-48-3 (3S,4S)-1,4-diphenyl-3-(1H-pyrrol-1-yl)azetidin-2-one 
• 1379469-45-0 (3R,4S)-1,4-diphenyl-3-(1H-pyrrol-1-yl)azetidin-2-one 
• 112383-87-6 1,4-diphenylazetidine-2,3-dione 
• 16311-94-7 cis-3-azido-1,4-diphenylazetidin-2-one 
• 64468-50-4 trans-1,4-Diphenyl-3-hydroxyazetidin-2-on 

Relevant articles and documents

Microwave-mediated synthesis of 3-unsubstituted β-lactams with aqueous trimethylborane

A new microwave-induced method for the preparation of 3-unsubstituted β-lactams is explored via aqueous trimethylborane-mediated reaction of the corresponding xanthates.

Reactions of acid chlorides/ketenes with 2-substituted 4,5-dihydro-4,4- dimethyl-1,3-thiazoles: Formation of penam derivatives

Addition reactions of acid chlorides with various 2-substituted 4,5-dihydro-4,4-dimethyl-5-(methylsulfanyl)-1,3-thiazoles under basic conditions were studied. Two kinds of products were obtained from these additions, β-lactams and non-β-lactam adducts. When the reaction was carried out with 4,5-dihydro-1,3-thiazoles with a Ph substituent at C(2), the reaction proceeded via formal [2+2] cycloaddition and led to the correspoding β-lactam. On the other hand, acid chlorides and 4,5-dihydro-1,3-thiazoles bearing an α-H-atom at the C(2)-substituent underwent C(α)- and/or N-addition reactions and furnished non-β-lactam adducts, i.e., C(α)- and/or N-acylated 1,3-thiazolidines. The attempted transformations of sulfonyl esters of exo-6-hydroxy penams to endo-6-azido penams failed, although they were successful with mono-β-lactams under the same conditions. Copyright

Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity

The synthesis of a series of 3-acetoxyazetidin-2-ones 3a-n and 3-hydroxyazetidin-2-ones 6a-j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-acetoxyazetidin-2-ones 11a-h which possess a free carboxylic acid group on the N-1 aryl ring were obtained by treatment of suitably substituted Schiff bases 10a-h with acetoxyacetyl chloride. The novel bicyclic structures 7-acetoxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 13 and 7-hydroxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 14 were also obtained. Many of the compounds displayed antifungal activity in vitro when evaluated against the pathogenic fungi Cryptococcus neoformans, Candida albicans, Candida tropicalis, Candida parapsilosis, Candida glabrata, and Trichosporon cutaneum, while 3-acetoxyazetidin-2-ones 11a-h containing a free carboxylic acid group on the N-1 aryl ring displayed antibacterial activity against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Bacillus subtilis, Klebsiella aerogenes and Escherischia coli.