(3aR,6S,7aR)-2,2-dimethyl-4'-(4-methylphenyl)-tetrahydro-2H-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]oxazolidine]-5',7-dione

• ChemBase ID: 140899
• Molecular Formular: C17H19NO6
• Molecular Mass: 333.33586
• Monoisotopic Mass: 333.12123733
• SMILES: Cc1ccc(cc1)N1C[C@@]2(C(=O)[C@H]3[C@@H](CO2)OC(O3)(C)C)OC1=O
• Canonical SMILES: Cc1ccc(cc1)N1C[C@@]2(OC1=O)OC[C@@H]1[C@H](C2=O)OC(O1)(C)C
• InChI: InChI=1S/C17H19NO6/c1-10-4-6-11(7-5-10)18-9-17(24-15(18)20)14(19)13-12(8-21-17)22-16(2,3)23-13/h4-7,12-13H,8-9H2,1-3H3/t12-,13-,17+/m1/s1
• InChIKey: WFKGDVVGAWYPFR-XNJGSVPQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,6S,7aR)-2,2-dimethyl-4'-(4-methylphenyl)-tetrahydro-2H-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]oxazolidine]-5',7-dione
• IUPAC Traditional name: (3aR,6S,7aR)-2,2-dimethyl-4'-(4-methylphenyl)-dihydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]oxazolidine]-5',7-dione
• Synonyms: (3aR,5′S,7aR)-Dihydro-2,2-dimethyl-3′-(4-methylphenyl)-spiro[6H-1,3-dioxolo[4,5-c]pyran-6,5′-oxazolidine]-2′,7(4H)-dione; Shi Epoxidation Oxazolidinone Methyl Catalyst; (3aR,5′S,7aR)-二氢-2,2-二甲基-3′-(4-甲基苯基)-螺[6H-1,3-二氧并[4,5-c]吡喃-6,5′-噁唑烷]-2′,7(4H)-二酮

Database IDs

• CAS Number: 403501-30-4
• MDL Number: MFCD10567035
• PubChem SID: 162235137
• PubChem CID: 11515494

CALCULATED PROPERTIES

• Acid pKa: 14.949068
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.9566796
• LogD (pH = 7.4): 2.9566796
• Log P: 2.9566796
• Molar Refractivity: 82.0553 cm^3
• Polarizability: 32.466488 Å^3
• Polar Surface Area: 74.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 149-154 °C
• Optical Rotation: [α]22/D -28.0°, c = 1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C17H19NO6

DETAILS

Sigma Aldrich - 693456

Application
Asymmetric epoxidation organocatalyst
Packaging
100, 500 mg in glass bottle