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

• ChemBase ID: 141667
• Molecular Formular: C18H21NO6
• Molecular Mass: 347.36244
• Monoisotopic Mass: 347.1368874
• SMILES: CCc1ccc(cc1)N1C[C@@]2(C(=O)[C@H]3[C@@H](CO2)OC(O3)(C)C)OC1=O
• Canonical SMILES: CCc1ccc(cc1)N1C[C@@]2(OC1=O)OC[C@@H]1[C@H](C2=O)OC(O1)(C)C
• InChI: InChI=1S/C18H21NO6/c1-4-11-5-7-12(8-6-11)19-10-18(25-16(19)21)15(20)14-13(9-22-18)23-17(2,3)24-14/h5-8,13-14H,4,9-10H2,1-3H3/t13-,14-,18+/m1/s1
• InChIKey: FLYFZOSQSKQBNR-LBTNJELSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,6S,7aR)-4'-(4-ethylphenyl)-2,2-dimethyl-tetrahydro-2H-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]oxazolidine]-5',7-dione
• IUPAC Traditional name: (3aR,6S,7aR)-4'-(4-ethylphenyl)-2,2-dimethyl-dihydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]oxazolidine]-5',7-dione
• Synonyms: (3aR,5′S,7aR)-3′-(4-Ethylphenyl)-dihydro-2,2-dimethyl-spiro[6H-1,3-dioxolo[4,5-c]pyran-6,5′-oxazolidine]-2′,7(4H)-dione; Shi Epoxidation Oxazolidinone Ethyl Catalyst; (3aR,5′S,7aR)-3′-(4-乙基苯基)-二氢-2,2-二甲基-螺[6H-1,3-二氧并[4,5-c]吡喃-6,5′-噁唑烷]-2′,7(4H)-二酮; 史氏环氧化噁唑烷酮乙基催化剂

Database IDs

• CAS Number: 879880-79-2
• MDL Number: MFCD17019350
• PubChem SID: 162235901
• PubChem CID: 11537539

CALCULATED PROPERTIES

• Acid pKa: 14.94943
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.4012482
• LogD (pH = 7.4): 3.4012482
• Log P: 3.4012482
• Molar Refractivity: 86.6563 cm^3
• Polarizability: 34.292847 Å^3
• Polar Surface Area: 74.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 139-143 °C
• Optical Rotation: [α]22/D -17.0°, c = 0.5 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C18H21NO6

DETAILS

Sigma Aldrich - 693448

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