(2R)-3,6-dimethoxy-2-(propan-2-yl)-2,5-dihydropyrazine

• ChemBase ID: 152288
• Molecular Formular: C9H16N2O2
• Molecular Mass: 184.23554
• Monoisotopic Mass: 184.12117776
• SMILES: CC(C)[C@@H]1C(=NCC(=N1)OC)OC
• Canonical SMILES: COC1=N[C@@H](C(=NC1)OC)C(C)C
• InChI: InChI=1S/C9H16N2O2/c1-6(2)8-9(13-4)10-5-7(11-8)12-3/h6,8H,5H2,1-4H3/t8-/m1/s1
• InChIKey: FCFWEOGTZZPCTO-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3,6-dimethoxy-2-(propan-2-yl)-2,5-dihydropyrazine
• IUPAC Traditional name: (3R)-3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazine
• Synonyms: (R)-2,5-Dimethoxy-3-isopropyl-3,6-dihydropyrazine; (R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine; (2R)-2,5-Dihydro-3,6-dimethoxy-2-(1-methylethyl)pyrazine; (-)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine; 2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine; (R)-Schollkopf Reagent; (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine; (R)-2,5-二甲氧基-3-异丙基-3,6-二氢吡嗪; (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪

Database IDs

• CAS Number: 109838-85-9
• MDL Number: MFCDN/AN/AN/A4N/A565; MFCD00040565
• Beilstein Number: 3542790
• PubChem SID: 24863173; 162246433
• PubChem CID: 736066

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.0652707
• LogD (pH = 7.4): 1.1099555
• Log P: 1.110556
• Molar Refractivity: 49.6423 cm^3
• Polarizability: 19.43399 Å^3
• Polar Surface Area: 43.18 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol
• Apperance: Clear Colourless Liquid
• Flash Point: 185 °F; 85 °C
• Density: 1.028 g/mL at 20 °C(lit.)
• Optical Rotation: [α]20/D -102±5°, c = 1% in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.0% (GC); 95+%
• Empirical Formula (Hill Notation): C9H16N2O2

DETAILS

Sigma Aldrich - 37286

Other Notes
Chiral auxiliary for the synthesis of α-amino acids1
Packaging
1, 5 mL in glass bottle

Toronto Research Chemicals - I824430

An inhibitor with antitumor activity.

REFERENCES

• Plumb, J., et al.: Mol. Cancer Ther., 2, 721 (2003)
• de Ruijter, A., et al.: Biochem. J., 370, 737 (2003)
• Dey, P., et al.: Curr. Med. Chem., 13, 2909 (2003)
• Maiso, P., et al.: Cancer Res., 66, 5781 (2003)
• Paris, M., et al.: J. Med. Chem., 51, 1505 (2