186613-02-5

Basic information

• Product Name: 3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE
• Synonyms: 3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE;3-(Acetyloxy)-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone;1-(4-Methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl acetate
• CAS NO: 186613-02-5
• Molecular Formula: C₁₈H₁₇NO₄
• Molecular Weight: 311.33
• Mol File: 186613-02-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.27
• Refractive Index: 1.588
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE(186613-02-5)
• EPA Substance Registry System: 3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE(186613-02-5)

Safety Data

• Hazardous Substances Data: 186613-02-5(Hazardous Substances Data)

Usage

General Description

3-(4-Methoxyphenyl)-2-oxo-4-phenylcyclobutyl acetate is a chemical compound with the molecular formula C18H16O4. It is a cyclobutyl acetate derivative with a substituent of 4-methoxyphenyl and a phenyl group. 3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE is commonly used in organic synthesis and pharmaceutical research due to its potential pharmacological properties. It may also have applications in the development of new drugs or as a building block in the synthesis of more complex organic molecules.

InChI:InChI=1/C19H18O4/c1-12(20)23-19-17(13-6-4-3-5-7-13)16(18(19)21)14-8-10-15(22-2)11-9-14/h3-11,16-17,19H,1-2H3

Upstream product

• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 13831-31-7 Acetoxyacetyl chloride 
• 124-63-0 methanesulfonyl chloride 
• 216094-54-1 (2R,3S)-N-benzoyl-O-(1-ethoxyethyl)-3-phenylisoserine 
• 104-94-9 4-methoxy-aniline 
• 100-52-7 benzaldehyde 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 141685-06-5 S-2-pyridyl acetoxythioacetate 

Downstream Products

• 1145983-10-3 (3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-methyl ester 
• 162993-22-8 (S)-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 37088-64-5 (S)-4-phenyl-2-azetidinone 
• 1067647-06-6 (S)-2-oxo-4-phenyl-azetidine-1-carboxylic acid tert-butyl ester 
• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 146924-91-6 (-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 146924-90-5 (+)-cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 194234-97-4 3-Hydroxy-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 101067-78-1 (+/-)-(3R,4S)-3-hydroxy-4-phenyl-N-(4-methoxyphenyl)azetidin-2-one 
• 194234-97-4 3-hydroxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 146924-94-9 (3R,4S)-(+)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 132127-31-2 (3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one 
• 155371-59-8 (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-phenylazetidin-2-one 

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

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.

Method for preparation of taxol using β-lactam

A β-lactam of the formula: STR1 wherein R1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R2 is hydrogen, alkyl, acyl, acetal, ethoxyethyl, or other hydroxyl protecting group; and R3 is aryl, substituted aryl, alky