158271-95-5

Basic information

• Product Name: (R)-1-(2-Hydroxy-1-phenylethyl)-1,5-dihydropyrrol-2-one
• Synonyms: (R)-1-(2-HYDROXY-1-PHENYLETHYL)-1,5-DIHYDROPYRROL-2-ONE;1-(2-HYDROXY-1-PHENYLETHYL)-1,5-DIHYDROPYRROL-2-ONE;1-[(1R)-2-hydroxy-1-phenylethyl]-2H-pyrrol-5-one
• CAS NO: 158271-95-5
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.24
• Mol File: 158271-95-5.mol

Chemical Properties

• Melting Point: 103 °C
• Boiling Point: 341.55°C (rough estimate)
• Flash Point: 217.1°C
• Appearance: /
• Density: 1.1255 (rough estimate)
• Vapor Pressure: 2.37E-08mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• PKA: 14.23±0.10(Predicted)
• CAS DataBase Reference: (R)-1-(2-Hydroxy-1-phenylethyl)-1,5-dihydropyrrol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(2-Hydroxy-1-phenylethyl)-1,5-dihydropyrrol-2-one(158271-95-5)
• EPA Substance Registry System: (R)-1-(2-Hydroxy-1-phenylethyl)-1,5-dihydropyrrol-2-one(158271-95-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 158271-95-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(2-Hydroxy-1-phenylethyl)-1,5-dihydropyrrol-2-one is used as a pharmaceutical intermediate for the development of new drugs targeting various medical conditions. Its unique chemical structure and chiral nature make it a promising candidate for drug discovery and design.
Used in Organic Synthesis:
(R)-1-(2-Hydroxy-1-phenylethyl)-1,5-dihydropyrrol-2-one is used as a valuable intermediate in the synthesis of other organic compounds, leveraging its distinctive structural features to create novel molecules with potential applications in various fields.
Research and Development:
(R)-1-(2-Hydroxy-1-phenylethyl)-1,5-dihydropyrrol-2-one is the subject of ongoing research to explore its properties and potential uses further. The scientific community continues to investigate its applications in different industries, aiming to unlock its full potential and contribute to advancements in various sectors.

InChI:InChI=1/C12H13NO2/c14-9-11(10-5-2-1-3-6-10)13-8-4-7-12(13)15/h1-7,11,14H,8-9H2/t11-/m0/s1

Upstream product

• 332-77-4 2,5-dihydro-2,5-dimethoxyfuran 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 56613-80-0 D-2-phenylglycinol 

Downstream Products

• 158271-98-8 3-Benzyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-1,5-dihydro-pyrrol-2-one 
• 158271-97-7 1-((R)-2-Hydroxy-1-phenyl-ethyl)-3-propyl-1,5-dihydro-pyrrol-2-one 
• 158271-96-6 1-((R)-2-Hydroxy-1-phenyl-ethyl)-3-methyl-1,5-dihydro-pyrrol-2-one 
• 205808-10-2 1-(2-hydroxy-1-phenylethyl)-pyrrolidin-2-one 
• 228098-62-2 (2R)-2-(2,5-Dihydro-2-oxopyrrol-1-yl)-2-phenylethylbenzoate 
• 133007-27-9 (3R,7aS)-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo[2,1-b]oxazol-5-one 
• 158272-01-6 (S)-3-Benzyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-3-methyl-1,3-dihydro-pyrrol-2-one 
• 228098-71-3 (2R)-2-<(3S,4S)-3,4-Dihydroxy-(2S)-2-<(1R)-1-hydroxy-3-phenylpropyl>-5-oxopyrrolidin-1-yl>-2-phenylethylbenzoate 
• 362045-69-0 (5R)-butyl-1-(2-hydroxy-(1'R)-phenylethyl)-pyrrolidin-2-one 

Relevant articles and documents

Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam

3-Alkyl pyrrolidones 9 were synthesized in good yield and high diastereoselectivity by α-alkylation of the new chiral non-racemic lactam 8 derived from (R)-(-)-phenylglycinol. After debenzylation and introduction of an electron-withdrawing group, 3-methylpyrrolidone 10 is easily hydrolyzed in a basic medium to produce γ-aminobutyric acid (GABA) analogue 13.

Diastereoselective bis-alkylation of chiral non-racemic α,β-unsaturated γ-lactams

A new chiral non-racemic γ-lactam 1 easily prepared in one step from (R)-(-)-phenylglycinol was bis-alkylated α to the carbonyl function in very high to complete diastereoselectivity. The stereochemistry at the so-formed chiral quaternary center was ascertained through an X-ray crystallographic study.