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

• ChemBase ID: 147491
• Molecular Formular: C10H17NO2
• Molecular Mass: 183.24748
• Monoisotopic Mass: 183.12592879
• SMILES: CC(C)[C@H]1CO[C@]2(N1C(=O)CC2)C
• Canonical SMILES: CC([C@H]1CO[C@]2(N1C(=O)CC2)C)C
• InChI: InChI=1S/C10H17NO2/c1-7(2)8-6-13-10(3)5-4-9(12)11(8)10/h7-8H,4-6H2,1-3H3/t8-,10-/m1/s1
• InChIKey: NUUDVADIQSLTCN-PSASIEDQSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 98203-44-2
• MDL Number: MFCD00467212
• PubChem SID: 24860069; 162241679
• PubChem CID: 853157

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.0748758
• LogD (pH = 7.4): 1.0748758
• Log P: 1.074876
• Molar Refractivity: 49.5133 cm^3
• Polarizability: 19.603642 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 70 °C/0.4 mmHg(lit.)
• Flash Point: 136.4 °F; 58 °C
• Density: 1.027 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.473(lit.)
• Optical Rotation: [α]27/D +90°, c = 2.8 in ethanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• UN Number: 1224
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1224 3/PG 3

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C10H17NO2

DETAILS

Sigma Aldrich - 334235

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
Packaging
5 g in glass bottle