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

• ChemBase ID: 146608
• Molecular Formular: C10H15NO2
• Molecular Mass: 181.2316
• Monoisotopic Mass: 181.11027873
• SMILES: CC(C)[C@H]1CO[C@]2(N1C(=O)C=C2)C
• Canonical SMILES: CC([C@H]1CO[C@]2(N1C(=O)C=C2)C)C
• InChI: InChI=1S/C10H15NO2/c1-7(2)8-6-13-10(3)5-4-9(12)11(8)10/h4-5,7-8H,6H2,1-3H3/t8-,10-/m1/s1
• InChIKey: JOXQDNAGAGXGOK-PSASIEDQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7aR)-7a-methyl-3-(propan-2-yl)-2H,3H,5H,7aH-pyrrolo[2,1-b][1,3]oxazol-5-one
• IUPAC Traditional name: (3S,7aR)-3-isopropyl-7a-methyl-2H,3H-pyrrolo[2,1-b][1,3]oxazol-5-one
• Synonyms: (3S-cis)-(+)-2,3-Dihydro-3-isopropyl-7a-methylpyrrolo[2,1-b]oxazol-5(7aH)-one; (3S-顺式)-(+)-2,3-二氢-3-异丙基-7a-甲基吡咯并[2,1-b]氧氮杂茂-5(7aH)-酮

Database IDs

• CAS Number: 116910-11-3
• MDL Number: MFCD06496252
• PubChem SID: 24869479; 162240802
• PubChem CID: 7157231

CALCULATED PROPERTIES

• Log P: 1.4573083
• Molar Refractivity: 50.3422 cm^3
• Polarizability: 19.35842 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4573002
• LogD (pH = 7.4): 1.4573082

PROPERTIES

Physical Property

• Melting Point: 46-49 °C(lit.)
• Optical Rotation: [α]20/D +41.0°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 26-36
• 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%
• Empirical Formula (Hill Notation): C10H15NO2

DETAILS

Sigma Aldrich - 458554

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
Packaging
1 g in glass bottle
250 mg in glass bottle