CAS 66673-40-3|(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone|(5R)-5-(hydroxymethyl)pyrrolidin-2-one|(5R)-5-(hydroxymethyl)pyrrolidin-2-one|(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone|D-Pyroglutaminol|(R)-...

General Information

Structure

Molecular Formula

C₅H₉NO₂

Molecular Mass

115.13046

Exact Mass

115.06332853

Charge

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

Canonic Smiles

OC[C@H]1CCC(=O)N1

Isomeric Smiles

N1C(=O)CC[C@@H]1CO

Calculated Properties

JChem

Acid pKa

14.226303

H Acceptors

H Donor

LogD (pH = 5.5)

-1.2099442

LogD (pH = 7.4)

-1.2099442

Log P

-1.2099442

Molar Refractivity

28.2204

Polarizability

11.098675

Polar Surface Area

49.33

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinoneD-Pyroglutaminol(R)-(-)-5-(羟甲基)-2-吡咯烷酮D-焦谷氨醇D-焦谷氨醇(R)-(-)-5-Hydroxymethylpyrrolidin-2-one(R)-5-(Hydroxymethyl)-2-pyrrolidinoneH-D-Pyr-ol(R)-(-)-5-(羟基甲基)-2-吡咯酮(R)-5-Oxopyrrolidine-2-methanol(5R)-5-(Hydroxymethyl)-2-pyrrolidinone

IUPAC Traditional name

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

IUPAC name

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

Names and Identifiers

Registration numbers

CAS Number

66673-40-3

PubChem SID

2487972816203323024862645

Beilstein Number

35879745728422

MDL Number

MFCD00077791

PubChem CID

7128291

Registration numbers

Properties

Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

366358

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

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

TRC

H948310

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

Molecule Details

References

PubChem Literature

From Data Sources

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

References

Bioactivity

PubChem BioAssay

Bioactivity