(1S,2R,4R)-3,3-dimethylspiro[bicyclo[2.2.1]heptane-2,3'-[1,4]oxazolidine]-5'-one

• ChemBase ID: 156589
• Molecular Formular: C11H17NO2
• Molecular Mass: 195.25818
• Monoisotopic Mass: 195.12592879
• SMILES: CC1([C@@H]2CC[C@@H](C2)[C@@]21COC(=O)N2)C
• Canonical SMILES: O=C1OC[C@@]2(N1)[C@H]1CC[C@@H](C2(C)C)C1
• InChI: InChI=1S/C11H17NO2/c1-10(2)7-3-4-8(5-7)11(10)6-14-9(13)12-11/h7-8H,3-6H2,1-2H3,(H,12,13)/t7-,8+,11-/m1/s1
• InChIKey: IIRXFQFVVUAFGC-VHSKPIJISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4R)-3,3-dimethylspiro[bicyclo[2.2.1]heptane-2,3'-[1,4]oxazolidine]-5'-one
• IUPAC Traditional name: (1S,2R,4R)-3,3-dimethylspiro[bicyclo[2.2.1]heptane-2,3'-[1,4]oxazolidine]-5'-one
• Synonyms: (-)-Chiracamphox; (5R)-6,6-Dimethyl-7,10-methylen-3-oxa-1-azaspiro[4.5]decan-2-one; (5R)-6,6-二甲基-7,10-亚甲基-3-噁-1-螺环-癸-2-酮

Database IDs

• CAS Number: 165038-32-4
• Beilstein Number: 6845010
• PubChem SID: 162250726; 24865482
• PubChem CID: 6553899

CALCULATED PROPERTIES

• Acid pKa: 12.861678
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.8508642
• LogD (pH = 7.4): 1.8508629
• Log P: 1.8508642
• Molar Refractivity: 51.4077 cm^3
• Polarizability: 20.719193 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 227-231 °C
• Optical Rotation: [α]20/D -48±2°, c = 5% in methylene chloride

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (CHN)
• Empirical Formula (Hill Notation): C11H17NO2

DETAILS

Sigma Aldrich - 40773

Other Notes
Chiral auxiliary for a wide range of asymmetric transformations1,2