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

• 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 
• 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 
• 492-38-6 2-phenylacrylic acid 

Downstream Products

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

Relevant articles and documents

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.

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.

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

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