5661-55-2

Usage

Uses

Used in Cognitive Enhancement:
4-Phenyl-2-azetidinone is used as a cognitive enhancer for its reported ability to improve memory, cognition, and physical performance. It is particularly favored by individuals seeking to enhance their cognitive capabilities in various settings, including academic, professional, and personal pursuits.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-Phenyl-2-azetidinone is used as a research compound for exploring its potential therapeutic applications. It is being studied for its possible efficacy in treating conditions such as anxiety, depression, and ADHD, with ongoing research aimed at confirming these indications and understanding its mechanisms of action.
Used in Regulatory Compliance:
In countries where Phenylpiracetam is regulated, 4-Phenyl-2-azetidinone is used in the development and enforcement of regulatory policies and guidelines. This ensures that its distribution, sale, and use are controlled to prevent abuse and misuse, safeguarding public health and safety.

InChI:InChI=1/C9H9NO/c11-9-6-8(10-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,11)

Upstream product

• 52341-70-5 N-chlorosulfonyl-4-phenylazetidin-2-one 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 14898-52-3 methyl 3-amino-3-phenylpropanoate 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 58521-58-7 (+/-)-trimethylsilyl β-(N-trimethylsilylamino)-β-phenylpropionate 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 7757-83-7 sodium sulfite 
• 645-45-4 hydrocinnamic acid chloride 
• 1514926-94-3 N-(5-methoxyquinolin-8-yl)-3-phenylpropanamide 
• 1514927-38-8 1-(5-methoxyquinolin-8-yl)-4-phenylazetidin-2-one 
• 97754-31-9 N-(4-methoxyphenyl)-3-phenylpropionamide 

Downstream Products

• 22117-14-2 (2-bromo-1-isocyanato-ethyl)-benzene 
• 117505-46-1 4-phenyl-2-pyrrolidinomethylazetidin-2-one 
• 76528-86-4 1-(4,5-Dihydro-3H-pyrrol-2-yl)-4-phenyl-azetidin-2-one 
• 4996-33-2 2-phenyl-2,6,7,8-tetahydro-3H-pyrrolo[1,2-a]pyrimidin-4-one 
• 89044-72-4 N-(4-chlorobutyl)-4-phenylazetidin-2-one 
• 4458-62-2 1-methyl-4-phenylazetidin-2-one 
• 74536-07-5 1-hydroxymethyl-4-phenyl-2-azetidinone 
• 89044-74-6 N-(5-bromopentyl)-4-phenylazetidin-2-one 
• 154218-80-1 N-(3-methylbut-2-enyl)-4-phenylazetidine-2-one 
• 110425-57-5 N-(8-bromooctyl)-4-phenylazetidin-2-one 
• 110425-66-6 (Z)-N-(4-chlorobut-2-enyl)-4-phenylazetidin-2-one 
• 110425-67-7 (E)-N-(4-bromobut-2-enyl)-4-phenylazetidin-2-one 
• 154218-88-9 N-(3-bromopropyl)-4-phenylazetidin-2-one 
• 89044-71-3 N-(3-bromobutyl)-4-phenylazetidin-2-one 

Relevant academic research and scientific papers

A Convenient Preparative Method for β-Lactams from β-Amino Acids Using Sulfenamide/Triphenylphosphine

β-,β-, and δ-Amino acids were easily cyclized in high yields to corresponding β-,γ-, and δ-lactams by treatment with N-alkyl-2-benzothiazolsulfenamide and triphenylphosphine.

SYNTHESIS OF 4-SUBSTITUED 2-AZETIDIONES

4-Substitued 2-azetidiones were obtained in excellent yields from the reaction of various cuprates with 4-acetoxy-2-azetidinone.

Copper-Catalyzed Oxidative Benzylic C(sp3)?H Cyclization for the Synthesis of β-Lactams

β-Lactams are important structural motifs because of their ubiquity in natural products and pharmaceuticals. We report herein a Cu-catalyzed intramolecular oxidative C(sp3)?H amidation for the synthesis of β-lactams using tBuOOtBu. This method

COMPOUNDS AND USES THEREOF

The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

2-Arylazetidines as ligands for nicotinic acetylcholine receptors

Alternative and complementary procedures were adopted for preparing 2-arylazetidine derivatives in moderate to good yields. Preliminary biological evaluation of 2-arylazetidines as ligands of nicotinic acetylcholine receptors allowed to identify chloro-substituted analogs as the most interesting congeners. The title compounds may be considered as suitable hit compounds for developing new nicotinic acetylcholine receptor ligands that may be safer than the currently available drugs targeting nicotinic acetylcholine receptors. Our described synthetic approaches enable facile access to a large number of diversely decorated azetidines for studying the structure-activity relationships and for refining the toxico-pharmacological profile of these agents.

Improved Synthetic Utility of a Sluggish Electrophile: Reaction of Chlorosulfonyl Isocyanate with Unreactive and Reactive Alkenes

Chlorosulfonyl isocyanate (CSI) is a sluggish electrophile in reactions with electron-deficient alkenes or with many monofluoroalkenes. The efficiency of these reactions is improved at temperatures between 15 and 25C because, at these temperatures, CSI an

Easy access to constrained peptidomimetics and 2,2-disubstituted azetidines by the unexpected reactivity profile of α-lithiated N-Boc-azetidines

The reactivity profile of lithiated N-Boc-2-arylazetidines has been investigated filling a gap in the chemistry of this class of four-membered heterocycles. Two unexpected and unprecedented results have been observed: an "ortho-effect" accounting for the regioselective functionalization of the azetidine ring, and self-condensation leading to new and interesting azetidine-based peptidomimetics.

Studies on N-activation for the lipase-catalyzed enantioselective preparation of β-amino esters from 4-phenylazetidin-2-one

The effect of N-substitution was examined for the enantio-selective lipase-catalyzed ring-opening reaction of racemic 4-phenylazetidin-2-one with methanol in dry organic solvents. Marked differences in the reactivity of various N-protected 4-phenylazetidin-2-ones were observed. Preparativescale reactions with Candida antarctica lipase B (Novozym 435 preparation) yielded N-acylated methyl (R)-3-amino-3- phenylpropanoates with enantiomeric excess (ee) values >99% in up to a 49% isolated yield, whereas Thermomyces lanuginosus lipase (Lipozyme TM IM) gave enantiomerically enriched methyl (S)-3-acetamido-3-phenylpropanoate. Candida antarctica lipase A catalyzed the cleavage of the N-chloroacetyl protective group, whereas all of the other examined lipases underwent the ring-opening reaction.

Poly-β-peptides from functionalized β-lactam monomers and antibacterial compositions containing same

Disclosed is a method of making β-polypeptides. The method includes polymerizing β-lactam-containing monomers in the presence of a base initiator and a co-initiator which is not a metal-containing molecule to yield the product β-polypeptides. Specifically disclosed are methods wherein the base initiator is potassium t-butoxide, lithium bis(trimethylsilyl)amide (LiN(TMS)2), potassium bis(trimethyl-silyl)amide, and sodium ethoxide, and the reaction is carried out in a solvent such as chloroform, dichloromethane, dimethylsulfoxide, or tetrahydrofuran.

Regioselective functionalization of 2-arylazetidines: Evaluating the ortho-directing ability of the azetidinyl ring and the α-directing ability of the N-substituent

The regioselective lithiation-functionalization of 2-arylazetidines has been explored. The nature of the N-substituent is mainly responsible for a regioselectivity switch. ortho-Lithiation occurred, using hexyllithium as a greener base, in N-alkylazetidines, while α-benzylic lithiation has been observed with N-Boc azetidines.