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
• Article Data: 7

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

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

Downstream Products

• 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 
• 20127-58-6 N-methyl-3-phenyl-2-pyrroline 

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.

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.

Reactivity of N,N-Dialkylamide Enolate Ions. Arylation of 1-Methyl-2-pyrrolidinone Enolate Ions by the SRN1 Mechanism

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