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

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

Uses

Used in Organic Synthesis:
3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE is used as a key intermediate in organic synthesis for the creation of more complex organic molecules. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of various compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE is used as a precursor in the development of new drugs. Its potential pharmacological properties make it a promising candidate for the discovery of novel therapeutic agents.
Used in Drug Development:
3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE may also have applications in the development of new drugs, where its specific chemical structure could contribute to the creation of innovative pharmaceuticals with unique mechanisms of action.
Overall, 3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE is a versatile chemical compound with significant applications in various fields, particularly in organic synthesis and pharmaceutical research, where its unique structure and potential pharmacological properties are highly valued.

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

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

Downstream Products

• 144790-01-2 (3R-cis)-3-acetyloxy-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 
• 146924-91-6 (-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 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 
• 144465-78-1 1-(4-Methoxyphenyl)-3-triisopropylsilyloxy-4-phenyl-2-azetidinone 
• 146924-90-5 (+)-cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 1067647-06-6 (S)-2-oxo-4-phenyl-azetidine-1-carboxylic acid tert-butyl ester 
• 37088-64-5 (S)-4-phenyl-2-azetidinone 

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

Process for preparation of enantiomerically pure S-(+)-N, N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine

The present invention relates to improved, efficient process for the preparation of enantiomerically pure S-(+)-N,N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine and pharmaceutically acid addition salts thereof. The present invention particularly provides a process for preparation of (3S, 4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one useful as a key intermediate for preparation of (s)-dapoxetine.

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.

Stereoselective one-pot synthesis of β-lactams by reaction of 2-pyridylthioesters with imines in the presence of AlBr3 or EtAlCl2

The reactions of some 2-pyridylthioesters with imines in the presence of AlBr3 or EtAlCl2 and of a tertiary amine afford β-lactams in a simple one-pot procedure with fair to high trans stereoselectivity. The condensation can be also

Method for preparation of taxol using an oxazinone

Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: STR1 wherein R1 is aryl, heteroaryl, alkyl, alkenyl, alkynyl or OR7 wherein R7 is alkyl, alkenyl, a

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

Method for preparation of taxol using an oxazinone

Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: STR1 wherein R1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R2 is hydrogen, ethoxyethyl, 2,2,2-tric