(3S,7aS)-7a-phenyl-3-(propan-2-yl)-hexahydropyrrolo[2,1-b][1,3]oxazol-5-one

• ChemBase ID: 138004
• Molecular Formular: C15H19NO2
• Molecular Mass: 245.31686
• Monoisotopic Mass: 245.14157885
• SMILES: CC(C)[C@H]1CO[C@]2(N1C(=O)CC2)c1ccccc1
• Canonical SMILES: CC([C@H]1CO[C@]2(N1C(=O)CC2)c1ccccc1)C
• InChI: InChI=1S/C15H19NO2/c1-11(2)13-10-18-15(9-8-14(17)16(13)15)12-6-4-3-5-7-12/h3-7,11,13H,8-10H2,1-2H3/t13-,15+/m1/s1
• InChIKey: USVVTHSUMLVZJC-HIFRSBDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7aS)-7a-phenyl-3-(propan-2-yl)-hexahydropyrrolo[2,1-b][1,3]oxazol-5-one
• IUPAC Traditional name: (3S,7aS)-3-isopropyl-7a-phenyl-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one
• Synonyms: (3S-cis)-(+)-Tetrahydro-3-isopropyl-7a-phenylpyrrolo[2,1-b]oxazol-5(6H)-one; (3S-顺)-(+)-四氢-3-异丙基-7a-苯基吡咯并[2,1-b]噁唑-5(6H)-酮

Database IDs

• CAS Number: 88670-16-0
• MDL Number: MFCD00075054
• PubChem SID: 162232263
• PubChem CID: 359375

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.7855933
• LogD (pH = 7.4): 2.7855933
• Log P: 2.7855933
• Molar Refractivity: 69.2117 cm^3
• Polarizability: 27.335468 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 56-58 °C(lit.)
• Optical Rotation: [α]25/D +70°, c = 1.5 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• 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): C15H19NO2

DETAILS

Sigma Aldrich - 335398

Application
Chiral bicyclic lactams such as this are useful templates for the asymmetric synthesis of a variety of natural and unnatural products.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