N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide

• ChemBase ID: 147620
• Molecular Formular: C13H19NO2
• Molecular Mass: 221.29546
• Monoisotopic Mass: 221.14157885
• SMILES: CCC(=O)N(C)[C@@H](C)[C@H](c1ccccc1)O
• Canonical SMILES: CCC(=O)N([C@H]([C@H](c1ccccc1)O)C)C
• InChI: InChI=1S/C13H19NO2/c1-4-12(15)14(3)10(2)13(16)11-8-6-5-7-9-11/h5-10,13,16H,4H2,1-3H3/t10-,13+/m0/s1
• InChIKey: NOUIRZGGWSLLAJ-GXFFZTMASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide
• IUPAC Traditional name: N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide
• Synonyms: (1S,2S)-(+)-Pseudoephedrinepropionamide; (1S,2S)-(+)-伪麻黄碱丙酰胺

Database IDs

• CAS Number: 159213-03-3
• MDL Number: MFCD03093975
• PubChem SID: 24878477; 162241807
• PubChem CID: 11138684

CALCULATED PROPERTIES

• Acid pKa: 13.863406
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.6283123
• LogD (pH = 7.4): 1.6283127
• Log P: 1.6283128
• Molar Refractivity: 63.8801 cm^3
• Polarizability: 25.039867 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 114-118 °C(lit.)
• Optical Rotation: [α]20/D +104°, c = 1 in methanol

Safety Information

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

Product Information

• Purity: 98%
• Optical Purity: ee: 99% (HPLC)
• Empirical Formula (Hill Notation): C13H19NO2

DETAILS

Sigma Aldrich - 540544

Application
Enolates of (1R,2R)-(-)- and (1S,2S)-(+)-pseudoephedrinepropionamide are substrates for diastereoselective alkylation reactions.1
Packaging
5 g in glass bottle