(3S,7aR)-7a-methyl-3-phenyl-2H,3H,5H,7aH-pyrrolo[2,1-b][1,3]oxazol-5-one

• ChemBase ID: 146022
• Molecular Formular: C13H13NO2
• Molecular Mass: 215.24782
• Monoisotopic Mass: 215.09462866
• SMILES: C[C@@]12C=CC(=O)N1[C@H](CO2)c1ccccc1
• Canonical SMILES: O=C1C=C[C@@]2(N1[C@H](CO2)c1ccccc1)C
• InChI: InChI=1S/C13H13NO2/c1-13-8-7-12(15)14(13)11(9-16-13)10-5-3-2-4-6-10/h2-8,11H,9H2,1H3/t11-,13-/m1/s1
• InChIKey: UFQSRYWJCHFOQX-DGCLKSJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7aR)-7a-methyl-3-phenyl-2H,3H,5H,7aH-pyrrolo[2,1-b][1,3]oxazol-5-one
• IUPAC Traditional name: (3S,7aR)-7a-methyl-3-phenyl-2H,3H-pyrrolo[2,1-b][1,3]oxazol-5-one
• Synonyms: (3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one; (3S-顺)-(+)-2,3-二氢-7a-甲基-3-苯基吡咯-[2,1-b]噁唑-5(7aH)-酮

Database IDs

• CAS Number: 143140-06-1
• MDL Number: MFCD00274331
• PubChem SID: 162240222; 24869482
• PubChem CID: 7157228

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.9374771
• LogD (pH = 7.4): 1.9374782
• Log P: 1.9374783
• Molar Refractivity: 61.2106 cm^3
• Polarizability: 23.415218 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 90-92 °C(lit.)
• Optical Rotation: [α]20/D +124°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Optical Purity: ee: ≥99% (HPLC)
• Empirical Formula (Hill Notation): C13H13NO2

DETAILS

Sigma Aldrich - 458570

Packaging
250 mg in glass bottle
Application
High levels of asymmetric induction1 have been obtained with this chiral bicyclic lactam in cycloadditions,2,3 alkylations,4,5,6 conjugate additions,7,8 annulations,9 and dihydroxylations.10