101067-53-2

Basic information

• Product Name: 2-Azetidinone, 4-(4-methoxyphenyl)-3-phenoxy-
• Synonyms: cis-4-(4-methoxyphenyl)-3-phenoxy-azetidin-2-one;4-(4-methoxyhenyl)-3-phenoxyazetidin-2-one;2-Azetidinone,4-(4-methoxyphenyl)-3-phenoxy;4-(4-methoxyphenyl)-3-phenoxy-2-azetidinone
• CAS NO: 101067-53-2
• Molecular Formula: C16H15NO3
• Molecular Weight: 269.29500
• Mol File: 101067-53-2.mol

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 4-(4-methoxyphenyl)-3-phenoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 4-(4-methoxyphenyl)-3-phenoxy-(101067-53-2)
• EPA Substance Registry System: 2-Azetidinone, 4-(4-methoxyphenyl)-3-phenoxy-(101067-53-2)

Safety Data

• Hazardous Substances Data: 101067-53-2(Hazardous Substances Data)

Upstream product

• 92-29-5 hydrobenzamide 
• 123-11-5 4-methoxy-benzaldehyde 
• 101067-50-9 2-phenyl-N-(4'-methoxybenzylidene)ethanolamine 
• 122-59-8 2-phenoxyacetic acid 
• 101067-65-6 [1-(4-Methoxy-phenyl)-meth-(Z)-ylidene]-(2-phenyl-2-trimethylsilanyloxy-ethyl)-amine 
• 96185-29-4 cis-3-phenoxy-4-(4'-methoxyphenyl)-1-(2'-phenyl-2'-tert-butyldimethylsiloxyethyl)azetidin-2-one 
• 102488-26-6 cis-4-(4'-methoxyphenyl)-3-phenoxy-1-(2'-phenyl-2'-trimethylsiloxyethyl)azetidin-2-one 
• 93681-42-6 2-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-1-phenyl-ethanol 
• 93681-46-0 [1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-(2-phenyl-2-trimethylsilanyloxy-ethyl)-amine 
• 93681-48-2 cis-4-(4'-methoxyphenyl)-3-phenoxy-1-(2'-phenyl-2'-hydroxyethyl)azetidin-2-one 
• 100-52-7 benzaldehyde 
• 15475-06-6 p-anisal-p-phenetidine 
• 701-99-5 Phenoxyacetyl chloride 
• 98767-92-1 (3S,4R)-1-(1-Hydroxy-2-oxo-2-phenyl-ethyl)-4-(4-methoxy-phenyl)-3-phenoxy-azetidin-2-one 

Relevant articles and documents

Synthesis of N1-unsubstituted (β-lactams : Introducing n1-(1'-thiophenyl)benzyl as an N-protecting group

A diastereoselective synthesis of (±) cis-β-lactams (5 and 6) via cycloaddition reaction of N1-(α-thiophenyl)benzyl imines (3) with acid chlorides (4) in the presence of triethyl amine is described. Deprotection of N1-(α-thiophenyl)benzyl group was achieved in good yields by oxidation using potassium persulfate.

Ceric ammonium nitrate on silica gel for solid-solid phase N-dearylation of -lactams

Silica gel-supported ceric ammonium nitrate (CAN-SiO2) has been found to be an effective reagent for the solid-solid phase and solvent-free N-dearylation of -lactams. The results have been compared with CAN alone in solution and solid-solid phase.

Exploring a benzyloxyaniline linker utilizing ceric ammonium nitrate (CAN) as a cleavage reagent: Solid-phase synthesis of N-unsubstituted β-lactams and secondary amides

(equation presented) A novel benzyloxyaniline linker that uses ceric ammonium nitrate (CAN) as a cleavage reagent is described. Its application in the solid-phase synthesis of N-unsubstituted β-lactams and secondary amides furnishes compounds in moderate to excellent yield (45-91%) and high purity (93-99%).

From solution-phase to 'on-column' N-dearylation of β-lactams by silica-supported ceric ammonium nitrate (CAN-SiO2)

It has been shown that N-(4-methoxy or 4-ethoxyphenyl) groups can be oxidatively removed by silica gel supported ceric ammonium nitrate (CAN-SiO 2) under mild conditions in solution and on column. The yields in these two methods were good to excellent and purification of products is simpler than the general method by CAN. Especially the 'on-column' reaction is mild, easy, efficient, and cheap. The lower mobility of CAN-SiO2 makes it safer to handle. Georg Thieme Verlag Stuttgart.

Synthesis of N-unsubstituted β-lactams from N-alkoxyphenyl-β- lactams with cobalt(III) fluoride

Mild and efficient oxidative N-dearylation of N-alkoxyphenyl-β-lactams with cobalt(III) fluoride proceeded in good to excellent yields to afford the corresponding N-unsubstituted β-lactams. Optimization of the solvent, molar ratio of reagents, time, and t

Solid-solid phase and solvent-free oxidative removal of N-(4-alkoxyphenyl) groups of monocyclic β-lactams with ceric ammonium nitrate as a cheap, simple, and efficient method

Five N-(4-methoxyphenyl)- and five N-(4-ethoxyphenyl)-β-lactams were prepared by ketene-imine [2+2] cycloaddition (Staudinger reaction). Then these 2-azetidinones were N-dearylated by grinding together with ceric ammonium nitrate without hazardous solvent

Synthesis of novel N-(4-ethoxyphenyl) azetidin-2-ones and their oxidative N-deprotection by ceric ammonium nitrate

It is shown that the N-(p-ethoxyphenyl) group on β-lactams can be oxidatively removed by ceric ammonium nitrate in good yield. Fourteen new N-(p-ethoxyphenyl)-2-azetidinones 8a-n were synthesized through standard [2+2] ketene-imine cycloadditions (Staudinger reaction). Treatment of these compounds with ceric ammonium nitrate yielded the N-dearylated 2-azetidinones 9a-n in good to excellent yields. The effects of solvent, molar equiv of CAN and different temperatures have been investigated and optimum conditions were established.

Synthesis of N1-unsubstituted β-lactams via a facile deprotection of N1-[(α-thiophenyl)benzyl] group

A diastereoselective synthesis of (±) c/s-β-1actams (5 and 6) via cycloaddition reactions of N1-(α-thiophenyl)benzyl imines (3) with acid chlorides (4) in the presence of triethylamine is described. The deprotection of N1-(α-thiophenyl)benzyl group has been achieved by oxidation using potassium persulfate to give N-unsubstituted β-lactams (7) in good yields.

Reagents and Synthetic Methods. Part 58. Synthesis of β-Lactams from Acetic Acids and Imines promoted by Vilsmeier Type Reagents

The development of a practical method for the stereospecific preparation of several 3-substituted β-lactams from acetic acids and imines is described.The key step of the method is the activation of the carboxy component by means of Vilsmeier type reagents.The preparation of some N-(2'-hydroxyethyl)-β-lactams and N-(p-dimethyl-t-butylsiloxyphenyl)-β-lactams as intermediates for N-H azetidinones is also reported.For the last compounds the steric bulk of the N-substituent is the key feature for a high cis-β-lactam formation.

PYRIDINE ASSISTED OXIDATIONS OF ALCOHOLS TO CARBONYL COMPOUNDS BY MEANS OF 3-CARBOXYPYRIDINIUM DICHROMATE (NDC) REAGENT.

3-carboxypyridinium dichromate (NDC), readly prepareted from nicotinic acid and chromium trioxide, is an efficient reagent for the oxidation of alcohols into carbonyl compounds in the presence of pyridine.The optimum molar ratio substrate:reagent:pyridine to ensure complete oxidation of starting material in a short reaction time was found 1:2.5:20 respectlively.A brief compouison between this reagent and pyridinium dichromate (PDC) is made.In contrast to the PDC reagent, NDC allows selective oxidation between benzylic alcohols and aliphatic alcohols.The NDC-pyridine system has been successfully extended to the oxidation of N-(2-hidroxy-2-phenyl or 2-methylethyl)-β-lactams into their corresponding carbonyl compounds as N-H azetidin-2-one precursor.In contrast, primary N-(2-hydroxyethyl)-β-lactams upon treatment with this reagent system afforded N-formylazetidin-2-ones.The influence of pyridine in oxidations by means of NDC is further shown in the conversion of hydroquinones into quinones.Another interesting feature associated with the use of this reagent is the ease of purification of the final products.