(2R,3R,8aS)-3-(hydroxymethyl)-8a-methyl-2-phenyl-hexahydro-2H-[1,3]oxazolo[3,2-a]pyridin-5-one

• ChemBase ID: 137335
• Molecular Formular: C15H19NO3
• Molecular Mass: 261.31626
• Monoisotopic Mass: 261.13649347
• SMILES: C[C@]12CCCC(=O)N1[C@@H]([C@H](O2)c1ccccc1)CO
• Canonical SMILES: OC[C@@H]1[C@H](O[C@@]2(N1C(=O)CCC2)C)c1ccccc1
• InChI: InChI=1S/C15H19NO3/c1-15-9-5-8-13(18)16(15)12(10-17)14(19-15)11-6-3-2-4-7-11/h2-4,6-7,12,14,17H,5,8-10H2,1H3/t12-,14-,15+/m1/s1
• InChIKey: HMPLCFQDHIGQMF-YUELXQCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,8aS)-3-(hydroxymethyl)-8a-methyl-2-phenyl-hexahydro-2H-[1,3]oxazolo[3,2-a]pyridin-5-one
• IUPAC Traditional name: (2R,3R,8aS)-3-(hydroxymethyl)-8a-methyl-2-phenyl-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridin-5-one
• Synonyms: [2S-(2α,3β,8aβ)]-(+)-Hexahydro-3-(hydroxymethyl)-8a-methyl-2-phenyl-5H-oxazolo[3,2-a]pyridin-5-one; [2S-(2α,3β,8aβ)]-(+)-六氢-3-(羟甲基)-8a-甲基-2-苯基-5H-噁唑并[3,2-a]吡啶-5-酮

Database IDs

• CAS Number: 116950-01-7
• MDL Number: MFCD00192204
• PubChem SID: 24864208; 162231598
• PubChem CID: 736006

CALCULATED PROPERTIES

• Acid pKa: 14.994332
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3692795
• LogD (pH = 7.4): 1.3692795
• Log P: 1.3692795
• Molar Refractivity: 70.9452 cm^3
• Polarizability: 27.965965 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 96-100 °C(lit.)
• Optical Rotation: [α]23/D +14°, c = 1 in ethanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C15H19NO3

DETAILS

Sigma Aldrich - 388114

Application
Chiral bicyclic lactams such as this are useful templates for asymmetric synthesis.1 High levels of asymmetric induction have been obtained in cycloadditions,2,3 alkylations,4,5,6 conjugate additions,7,8 annulations,9 and dihydroxylations.10
Packaging
5 g in glass bottle