(3R)-3-(propan-2-yl)piperazine-2,5-dione

• ChemBase ID: 145304
• Molecular Formular: C7H12N2O2
• Molecular Mass: 156.18238
• Monoisotopic Mass: 156.08987763
• SMILES: CC(C)[C@@H]1C(=O)NCC(=O)N1
• Canonical SMILES: O=C1CNC(=O)[C@H](N1)C(C)C
• InChI: InChI=1S/C7H12N2O2/c1-4(2)6-7(11)8-3-5(10)9-6/h4,6H,3H2,1-2H3,(H,8,11)(H,9,10)/t6-/m1/s1
• InChIKey: IULFBTHVPRNQCG-ZCFIWIBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-(propan-2-yl)piperazine-2,5-dione
• IUPAC Traditional name: (3R)-3-isopropylpiperazine-2,5-dione
• Synonyms: (R)-(-)-3-Isopropyl-2,5-piperazinedione; (R)-3-Isopropyl-2,5-piperazinedione; (R)-3-Isopropyl-2,5-piperizinedione; (R)-3-ISOPROPYL-2,5-PIPERAZINEDIONE; (R)-(-)-3-异丙基-2,5-哌嗪二酮; (R)-3-异丙基-2,5-哌嗪二酮

Database IDs

• CAS Number: 143673-66-9
• MDL Number: MFCD00210060
• Beilstein Number: 82869
• PubChem SID: 24868402; 162239511
• PubChem CID: 736000

CALCULATED PROPERTIES

• Acid pKa: 11.141649
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.75430787
• LogD (pH = 7.4): -0.75437677
• Log P: -0.75430703
• Molar Refractivity: 39.0965 cm^3
• Polarizability: 15.37034 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 256-262 °C; 258-262 °C(lit.)
• Optical Rotation: [α]20/D -28.0±2°, c = 1 in H2O; [α]20/D -31.5°, c = 1 in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.5% (sum of enantiomers, HPLC); 95+%; 97%; 98%
• Grade: puriss.
• Empirical Formula (Hill Notation): C7H12N2O2
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 448362

Application
Chiral auxiliary developed by Professor Schöllkopf for the enantioselective synthesis of α-amino acids.1,2,3
Packaging
1 g in glass bottle