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

• ChemBase ID: 137294
• Molecular Formular: C18H17NO2
• Molecular Mass: 279.33308
• Monoisotopic Mass: 279.12592879
• SMILES: c1ccc(cc1)[C@H]1CO[C@]2(N1C(=O)CC2)c1ccccc1
• Canonical SMILES: O=C1CC[C@@]2(N1[C@H](CO2)c1ccccc1)c1ccccc1
• InChI: InChI=1S/C18H17NO2/c20-17-11-12-18(15-9-5-2-6-10-15)19(17)16(13-21-18)14-7-3-1-4-8-14/h1-10,16H,11-13H2/t16-,18+/m1/s1
• InChIKey: DKQMLBIEOBOMDP-AEFFLSMTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7aS)-3,7a-diphenyl-hexahydropyrrolo[2,1-b][1,3]oxazol-5-one
• IUPAC Traditional name: (3S,7aS)-3,7a-diphenyl-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one
• Synonyms: (3S-cis)-(+)-Tetrahydro-3,7a-diphenylpyrrolo[2,1-b]oxazol-5(6H)-one; (3S-顺)-(+)-四氢-3,7a-二苯基吡咯并[2,1-b]噁唑-5(6H)-酮

Database IDs

• CAS Number: 161970-71-4
• MDL Number: MFCD00274329
• PubChem SID: 24869475; 162231558
• PubChem CID: 854037

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.2657633
• LogD (pH = 7.4): 3.2657633
• Log P: 3.2657633
• Molar Refractivity: 80.0801 cm^3
• Polarizability: 31.40756 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 82-85 °C(lit.)
• Optical Rotation: [α]20/D +113°, c = 1 in chloroform

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): C18H17NO2

DETAILS

Sigma Aldrich - 458538

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