(2R)-(2,3,4,5-13C4,1-15N)pyrrolidine-2-carboxylic acid

• ChemBase ID: 176971
• Molecular Formular: C5H9NO2
• Molecular Mass: 121.08714309
• Monoisotopic Mass: 121.07713762
• SMILES: [13CH2]1[13CH2][13CH2][15NH][13C@H]1[13C](=O)O
• Canonical SMILES: O[13C](=O)[13C@H]1[13CH2][13CH2][13CH2][15NH]1
• InChI: InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1/i1+1,2+1,3+1,4+1,5+1,6+1
• InChIKey: ONIBWKKTOPOVIA-WAPLMMNXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-(2,3,4,5-^1^3C₄,1-^1^5N)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2R)-(2,3,4,5-^1^3C₄,1-^1^5N)pyrrolidine-2-carboxylic acid
• Synonyms: (+)-(R)-Proline-13C5,15N; (R)-(+)-Proline-13C5,15N; (R)-2-Carboxypyrrolidine-13C5,15N; (R)-Proline-13C5,15N; (R)-Pyrrolidine-2-carboxylic Acid-13C5,15N; D-(+)-Proline-13C5,15N; D-Proline-13C5,15N

Database IDs

• PubChem SID: 164232881
• PubChem CID: 71751801

CALCULATED PROPERTIES

• Acid pKa: 1.9406707
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.5687168
• LogD (pH = 7.4): -2.5686643
• Log P: -2.5686383
• Molar Refractivity: 28.0643 cm^3
• Polarizability: 11.294152 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P755992

Labelled D-Proline (P755990). Used in the synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine and formal synthesis of (-)-Lasubine II and (+)-Cermizine C.

REFERENCES

• Gawley, R., et al.: Org. Biomol. Chem., 4, 4285 (2006)