101067-80-5

Basic information

• Product Name: trans-3-hydroxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one
• CAS NO: 101067-80-5
• Molecular Weight: 269.3
• Mol File: 101067-80-5.mol

Chemical Properties

• CAS DataBase Reference: trans-3-hydroxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3-hydroxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one(101067-80-5)
• EPA Substance Registry System: trans-3-hydroxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one(101067-80-5)

Safety Data

• Hazardous Substances Data: 101067-80-5(Hazardous Substances Data)

Upstream product

• 40339-42-2 4-methoxy-N-[(1Z)-phenylmethylene]aniline 
• 41625-51-8 trimethylsiloxyacetic acid 
• 94612-33-6 1-(4-methoxyphenyl)-4-phenylazetidine-2,3-dione 
• 131968-76-8 (+/-)-(3R,4S)-3-acetoxy-N-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 100-52-7 benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 57469-50-8 2-hydroxyacetyl chloride 
• 194234-97-4 3-Hydroxy-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 186613-02-5 cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one 
• 19340-68-2 1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 63160-12-3 2-[(4-methylphenyl)sulfonyl]-3-phenyl-oxaziridine 
• 146924-91-6 (-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 

Downstream Products

• 146924-95-0 (-)-(3S,4R)-3-acetoxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 162599-35-1 cis-1-(p-anisyl)-3'S-(4,6-diacetoxy-2,3-enyl-α-O-glycoside)-4R-phenyl-azetidin-2-one 
• 162458-86-8 cis-1-(p-anisyl)-3'R-(4,6-diacetoxy-2,3-enyl-α-O-glycoside)-4S-phenyl-azetidin-2-one 
• 94612-33-6 1-(4-methoxyphenyl)-4-phenylazetidine-2,3-dione 
• 146924-91-6 (-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 1415716-33-4 C₂₁H₂₅NO₄ 

Relevant articles and documents

Ni-Catalyzed asymmetric reduction of α-keto-β-lactams: via DKR enabled by proton shuttling

Chiral α-hydroxy-β-lactams are key fragments of many bioactive compounds and antibiotics, and the development of efficient synthetic methods for these compounds is of great value. The highly enantioselective dynamic kinetic resolution (DKR) of α-keto-β-lactams was realized via a novel proton shuttling strategy. A wide range of α-keto-β-lactams were reduced efficiently and enantioselectively by Ni-catalyzed asymmetric hydrogenation, providing the corresponding α-hydroxy-β-lactam derivatives with high yields and enantioselectivities (up to 92% yield, up to 94% ee). Deuterium-labelling experiments indicate that phenylphosphinic acid plays a pivotal role in the DKR of α-keto-β-lactams by promoting the enolization process. The synthetic potential of this protocol was demonstrated by its application in the synthesis of a key intermediate of Taxol and (+)-epi-Cytoxazone. This journal is

Synthesis and biological evaluation of novel larotaxel analogues

Taxoids are a class of successful drugs and have been successfully used in chemotherapy for a variety of cancer types. However, despite the hope and promises that these taxoids have engendered, their utility is hampered by some clinic limitations. Extensive structure-activity relationship (SAR) studies of toxoids have been performed in many different laboratories. Whereas, SAR studies that based on the new-generation toxoid, larotaxel, have not been reported yet. In view of the advantages in preclinical and clinical data of larotaxel over former toxoids, new taxoids that strategicly modified at the C3’/C3′-N and C2 positions of larotaxel were designed, semi-synthesized, and examined for their potency and efficacy in vitro. As a result, it has been shown that the majority of these larotaxel analogues are exceptionally potent against both drug-sensitive tumor cells and tumor cells with drug resistance arising from P-glycoprotein over expression. Further in vivo antitumor efficacies investigations revealed A2 might be a potent antitumor drug candidate for further preclinical evaluation.

Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines—An Experimental and Computational Approach

The reactivity of 3-oxo-β-lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin-2-one C4 substituent, this reaction was shown to selectively produce 3-imino-β-lactams (through dehydration), α-aminoamides (thr

A mild and selective reduction of β-lactams: Rh-catalyzed hydrosilylation towards important pharmacological building blocks

Four-membered N-heterocyclic compounds exhibit a broad range of pharmacological activities. Herein, we report a useful rhodium-catalyzed protocol for the activation of phenylsilane to reduce tertiary β-lactams. Reaction with the tertiary amides was select

A novel asymmetric synthesis of 3-(1H-pyrrol-1-yl)-substituted β-lactams via a bismuth nitrate-catalyzed reaction

The reaction of racemic α-keto β-lactams 5a-5c with the commercially available chiral compound trans-4-hydroxy-L-proline (6) in the presence of a catalytic amount of Bi(NO3)3·5 H 2O in EtOH gave a diastereoisomer mixture o

Stereospecific novel glycosylation of hydroxy β-lactams via iodine-catalyzed reaction: A new method for optical resolution

Glycosylation of racemic and optically active α-hydroxy β-lactams by reaction with a few glycal derivatives in the presence of catalytic amounts of iodine has provided stereospecific formation of α-glycosides. This method has been extended for the prepara

Arthrobacter sp.: a lipase of choice for the kinetic resolution of racemic arylazetidinone precursors of taxanoid side chains

The native strain of Arthrobacter sp. (MTCC 5125) bearing a lipase has been found to be the most effective in the kinetic resolution of racemic arylazetidinones for producing cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone, cis-(3R,4S)-3-

Reductive ring opening of 2-azetidinones promoted by sodium borohydride

Variously substituted 2-azetidinones 3 and 4 were reacted with sodium borohydride in aqueous isopropanol giving 3-aminopropan-1,2-dioles 5 and 7. Reaction extent was dependent upon the substitution pattern in the 3- and 4-positions of the 2-azetidinone ri

N-Methylthio β-lactam antibacterials: Effects of the C 3/C4 ring substituents on anti-MRSA activity

N-Thiolated β-lactams are a new family of antibacterials that inhibit the growth of Staphylococcus bacteria. Unlike other β-lactam drugs, these compounds retain their full antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) strains and operate through a different mode of action. The structural features, which give these lactams their biological activity, have not yet been completely defined. Earlier efforts in our laboratory established that the N-organothio substituent is essential for antimicrobial activity while other groups at C3 and C4 on the lactam ring play a more subtle role. In this present study, we investigate these effects by varying the polar and steric nature of the ring substituents at these two centers. From the data presented herein, it appears that there is a need to balance the lipophilic character of the C3/C4 groups to obtain an optimal anti-MRSA activity. The structure-bioactivity profiles more closely relate to the compound's ability to penetrate the bacterial cell membrane to sites of action within the cytoplasm rather than to any specific non-bonding interactions with a biological target. Based on these results, a model for the compounds' mode of action is presented.

An efficient and simple procedure for the preparation of α-keto-β-lactams

The methods for the preparation of α-keto-β-lactams described in the literature are generally specific for a particular target molecule and lack generality. A short route to several of these compounds has been developed and is described in this communication. The protocol based on an efficient cyclization procedure followed by hydrolysis and oxidation allows preparation of α-keto-β-lactams 5a-g with sensitive substituents. Wiley-VCH Verlag GmbH, 2000.