37088-64-5

Basic information

• Product Name: 2-Azetidinone, 4-phenyl-, (S)-
• CAS NO: 37088-64-5
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Mol File: 37088-64-5.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 4-phenyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 4-phenyl-, (S)-(37088-64-5)
• EPA Substance Registry System: 2-Azetidinone, 4-phenyl-, (S)-(37088-64-5)

Safety Data

• Hazardous Substances Data: 37088-64-5(Hazardous Substances Data)

Usage

Chemical compound

2-Azetidinone, 4-phenyl-, (S)-

Pharmaceutical drug used for

Neuropathic pain
Anxiety disorders
Adjunct therapy for partial seizures

Mechanism of action

Binds to the alpha 2-delta subunit of voltage-gated calcium channels in the central nervous system

Effects

Reduces release of neurotransmitters
Decreases excitability of neurons

Administration

Orally, in the form of a capsule

Side effects

Drowsiness
Dizziness
Other potential side effects

Caution

Should be used under the guidance of a healthcare professional

Upstream product

• 5661-55-2 4-phenylazetidin-2-one 
• 1514926-95-4 1-(8-quinolinyl)-4-phenyl-azetidinone 
• 100-42-5 styrene 
• 67-56-1 methanol 
• 110425-62-2 N-(2-chloroacetyl)-4-phenylazetidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 146924-91-6 (-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 186613-02-5 cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 1145983-10-3 (3S,4R)-dithiocarbonic acid O-[1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl] ester S-methyl ester 
• 1169704-24-8 C₁₇H₂₇NO₃S 
• 196929-85-8 (R)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 97-72-3 2-Methylpropionic anhydride 
• 162993-22-8 (S)-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 

Downstream Products

• 82359-84-0 1,4-bis<(S)-(-)-2-oxo-4-phenyl-1,5-diazacyclooctanyl>-butane 
• 88931-11-7 (S)-(-)-4-phenyl-1,5-diazacyclooctan-2-one 
• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 1628434-28-5 (S)-1-ethyl-4-phenylazetidin-2-one 
• 1331772-06-5 C₁₂H₁₃NO₂ 
• 1067647-06-6 (S)-2-oxo-4-phenyl-azetidine-1-carboxylic acid tert-butyl ester 
• 872726-33-5 CP 100263 dihydrochloride 
• 65094-32-8 (S)-4-phenyl-9-(3-phenylprop-2-enoyl)-1,5,9-triazacyclotridecan-2-one 

Relevant articles and documents

Asymmetric synthesis of β-lactam via palladium-catalyzed enantioselective intramolecular c(sp3)-h amidation

β-Lactams are important scaffolds in drug design and frequently used as reactive intermediates in organic synthesis. Catalytic reactions featuring intramolecular C-H amidation of alkyl carboxamide substrates could provide a straightforward disconnection strategy for β-lactam synthesis. Herein, we report a streamlined method for asymmetric synthesis of β-aryl β-lactams from propanoic acid and aryl iodides via Pd-catalyzed sequential C(sp3)-H functionalization. The lactam-forming reaction provides an example of PdII-catalyzed enantioselective intramolecular C(sp3)-H amidation reaction and proceeds up to 94% ee. The use of a 2-methoxy-5-chlorophenyl iodide oxidant is critical to control the competing reductive elimination pathways of the PdIV intermediate to achieve the desired chemoselectivity. Mechanistic studies suggest that both steric and electronic effects of the unconventional aryl iodide oxidant are responsible for controlling the competing C-N versus C-C reductive elimination pathways of the PdIV intermediate.

HPLC enantioseparation on a homochiral MOF-silica composite as a novel chiral stationary phase

The last frontier in the development of chiral stationary phases for chromatographic enantioseparation involves homochiral metal-organic frameworks (MOFs). Using enantiopure (R)-2,2′-dihydroxy-1,1′-binaphthalene-6,6′-dicarboxylic acid as a starting material, we prepared three homochiral MOFs that were further used as chiral stationary phases for high-performance liquid chromatography to separate the enantiomers of various kinds of racemic sulfoxides, sec-alcohols, β-lactams, benzoins, flavanones and epoxides. The experimental results showed excellent performances for enantioseparation, and highlighted that enantioseparation on homochiral MOF columns is practical.

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.