54520-82-0

Basic information

• Product Name: 1-methyl-3-phenylpyrrolidin-2-one
• CAS NO: 54520-82-0
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.227
• Mol File: 54520-82-0.mol

Chemical Properties

• Boiling Point: 325°C at 760 mmHg
• Flash Point: 134.4°C
• Density: 1.092g/cm³
• Vapor Pressure: 0.000236mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: 1-methyl-3-phenylpyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-3-phenylpyrrolidin-2-one(54520-82-0)
• EPA Substance Registry System: 1-methyl-3-phenylpyrrolidin-2-one(54520-82-0)

Safety Data

• Hazardous Substances Data: 54520-82-0(Hazardous Substances Data)

Usage

Origin

Derived from the opiate alkaloid thebaine

Structural relation

Related to the opioid analgesic drug prodine

Schedule

Schedule I controlled substance in the United States

Effects

Similar to other opioid drugs, such as pain relief and sedation

Risks

High potential for abuse and addiction, associated with severe poisoning and death when illicitly produced and distributed in the 1980s.

Upstream product

• 872-50-4 1-methyl-pyrrolidin-2-one 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 55164-56-2 1-methyl-3-phenyl-1,5-dihydro-2H-pyrrol-2-one 
• 492-38-6 2-phenylacrylic acid 
• 79232-58-9 3-Phenyl-2-oxo-3-pyrrolidincarbonsaeure-ethylester 
• 83-13-6 diethyl 2-phenylmalonate 
• 1159252-68-2 C₁₂H₁₃NO₃ 
• 92647-37-5 diethyl (2-cyanomethyl)-2-phenylpropanedioate 

Downstream Products

• 20127-58-6 N-methyl-3-phenyl-2-pyrroline 
• 1159252-75-1 meso-3,3-bis(1-methyl-3-phenylpyrrolidin-2-one) 
• 1159252-73-9 C₂₃H₂₄N₂O₃ 
• 1159252-72-8 C₂₃H₂₄N₂O₃ 
• 20395-76-0 (+/-)-desdimethoxymesembrine 

Relevant articles and documents

Taming Radical Pairs in the Crystalline Solid State: Discovery and Total Synthesis of Psychotriadine

Solid-state photodecarbonylation is an attractive but underutilized methodology to forge hindered C-C bonds in complex molecules. This study discloses the use of this reaction to assemble the vicinal quaternary stereocenter motif present in bis(cyclotryptamine) alkaloids. Our strategy was enabled by experimental and computational investigations of the role of substrate conformation on the success or failure of the solid-state photodecarbonylation reaction. This informed a crystal engineering strategy to optimize the key step of the total synthesis. Ultimately, this endeavor culminated in the successful synthesis of the bis(cyclotryptamine) alkaloid "psychotriadine,"which features the elusive piperidinoindoline framework. Psychotriadine, a previously unknown compound, was identified in the extracts of the flower Psychotria colorata, suggesting it is a naturally occurring metabolite.

Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent "Ene"-Reductases

Non-natural photoenzymatic reactions reported to date have depended on the excitation of electron donor-acceptor complexes formed between substrates and cofactors within protein active sites to facilitate electron transfer. While this mechanism has unlocked new reactivity, it limits the types of substrates that can be involved in this area of catalysis. Here we demonstrate that direct excitation of flavin hydroquinone within "ene"-reductase active sites enables new substrates to participate in photoenzymatic reactions. We found that by using photoexcitation these enzymes gain the ability to reduce acrylamides through a single electron transfer mechanism.

Erratum: Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent 'Ene'-Reductases (J. Am. Chem. Soc. (2021) 143:4 (1735-1739) DOI: 10.1021/jacs.0c11494)

Support by the Department of Energy was inadvertently left out of the Acknowledgments and a coauthor's name was misspelled in the Supporting Information. The scientific part of the manuscript remains unchanged. The complete correct Acknowledgment paragraph is as follows.

Palladium-Catalyzed Inter- and Intramolecular α-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles

2A palladium-catalyzed α-arylation of amides is reported. Intermolecular arylation of N,N-dimethylamides and lactams occurs using aryl halides, silylamide base, and a palladium catalyst. Intramolecular arylation of N-(2-halophenyl)amides occurs using alkoxide base and a palladium catalyst. The palladium catalyst was formed in situ from Pd(dba)2 (dba = trans,trans-dibenzylidene acetone) and BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthalene). Although the intermolecular arylation of amides is less general than that reported previously for ketones, unfunctionalized and electron-rich aryl halides gave α-arylamides in 48-75% yield and N-methyl-α-phenylpyrrolidinone in 49% yield. These reactions provided the highest yields yet reported for regioselective amide arylations. Intramolecular amide arylation of 2-bromoanilides gave oxindoles in 52-82% yield. Mono- and disubstituted acetanilides gave 1,3-di- and 1,3,3-trisubstituted oxindoles. The use of dioxane, rather than THF, solvent was important for some of the amide arylations.

A short synthesis of (±)-mesembrine

An efficient synthesis of (±)-mesembrine and (±)-desdimethoxymesembrine from N-methyl-2-pyrrolidone is reported.