(2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid

• ChemBase ID: 69932
• Molecular Formular: C13H15NO5
• Molecular Mass: 265.2619
• Monoisotopic Mass: 265.09502259
• SMILES: N1([C@@H](C[C@H](C1)O)C(=O)O)C(=O)OCc1ccccc1
• Canonical SMILES: O[C@H]1CN([C@@H](C1)C(=O)O)C(=O)OCc1ccccc1
• InChI: InChI=1S/C13H15NO5/c15-10-6-11(12(16)17)14(7-10)13(18)19-8-9-4-2-1-3-5-9/h1-5,10-11,15H,6-8H2,(H,16,17)/t10-,11+/m1/s1
• InChIKey: WWVCWLBEARZMAH-MNOVXSKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid
• Synonyms: N-Cbz-Hydroxy-L-proline; Z-L-4-Hydroxyproline; Z-Hyp-OH; Z-Hyp-OH; trans-4-Hydroxy-L-proline, N-CBZ protected; (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, N-CBZ protected; (2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid; N-Cbz-羟基-L-脯氨酸; Z-L-4-羟脯氨酸

Database IDs

• CAS Number: 13504-85-3
• EC Number: 236-831-2
• MDL Number: MFCD00037329
• Beilstein Number: 90295
• PubChem SID: 24890283; 162035657
• PubChem CID: 391517

CALCULATED PROPERTIES

• Acid pKa: 3.6478767
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.1402832
• LogD (pH = 7.4): -2.6168594
• Log P: 0.7088675
• Molar Refractivity: 65.1843 cm^3
• Polarizability: 25.615402 Å^3
• Polar Surface Area: 87.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 104-107 °C
• Optical Rotation: [α]20/D -54±1°, c = 2% in ethanol
• Hydrophobicity(logP): 1.319

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (T); 95%; 95+%
• Empirical Formula (Hill Notation): C13H15NO5

DETAILS

Sigma Aldrich - 96310

Packaging
5, 25 g in glass bottle