(5R)-5-(hydroxymethyl)pyrrolidin-2-one

• ChemBase ID: 67495
• Molecular Formular: C5H9NO2
• Molecular Mass: 115.13046
• Monoisotopic Mass: 115.06332853
• SMILES: N1C(=O)CC[C@@H]1CO
• Canonical SMILES: OC[C@H]1CCC(=O)N1
• InChI: InChI=1S/C5H9NO2/c7-3-4-1-2-5(8)6-4/h4,7H,1-3H2,(H,6,8)/t4-/m1/s1
• InChIKey: HOBJEFOCIRXQKH-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-(hydroxymethyl)pyrrolidin-2-one
• IUPAC Traditional name: (5R)-5-(hydroxymethyl)pyrrolidin-2-one
• Synonyms: (R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone; H-D-Pyr-ol; (R)-(-)-5-Hydroxymethylpyrrolidin-2-one; D-Pyroglutaminol; (R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone; (R)-5-(Hydroxymethyl)-2-pyrrolidinone; (5R)-5-(Hydroxymethyl)-2-pyrrolidinone; (R)-5-Oxopyrrolidine-2-methanol; (R)-(-)-5-(羟基甲基)-2-吡咯酮; D-焦谷氨醇; D-焦谷氨醇; (R)-(-)-5-(羟甲基)-2-吡咯烷酮

Database IDs

• CAS Number: 66673-40-3
• MDL Number: MFCD00077791
• Beilstein Number: 3587974; 5728422
• PubChem SID: 24862645; 162033230; 24879728
• PubChem CID: 7128291

CALCULATED PROPERTIES

• Acid pKa: 14.226303
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.2099442
• LogD (pH = 7.4): -1.2099442
• Log P: -1.2099442
• Molar Refractivity: 28.2204 cm^3
• Polarizability: 11.098675 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dimethylformamide; Water
• Apperance: White Solid; 白色结晶粉末
• Melting Point: 79-81°C; 79-85 °C; 83-85 °C(lit.); 83-85°C; 86-88°C
• Boiling Point: 147-149 °C/0.06 mmHg(lit.); 147-149°C/0.06 mm; 147-149°C/0.06m
• Optical Rotation: [α]/D -30.5±2.0°, c = 5 in ethanol; [α]20/D -31°, c = 5 in ethanol; -30 (c=2 in ethanol); -31°(c = 2% in EtOH)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC); 95+%; 98%; 99%
• Grade: puriss.
• Empirical Formula (Hill Notation): C5H9NO2

DETAILS

Sigma Aldrich - 366358

Packaging
1, 5 g in glass bottle
Application
Serves as a building block in the synthesis of diphthamide.1

Sigma Aldrich - 55820

Other Notes
Versatile chiral building block and auxiliary, used e.g. for the synthesis of azaprostaglandins or 4,5-diaminovalerate1,2,3; The bicyclic N,O-benzylidene acetal allows enantioselective derivatization of the pyrrolidinone nucleus4,5

Toronto Research Chemicals - H948310

A 2-pyrrolidone derivative for therapeutic use as prostanoid receptor agonist.

REFERENCES

• Naylor, A., et al.: J. Med. Chem., 37, 2138 (1994)