(1R,2S,3R,4S)-1,7,7-trimethyl-3-(morpholin-4-yl)bicyclo[2.2.1]heptan-2-ol

• ChemBase ID: 135559
• Molecular Formular: C14H25NO2
• Molecular Mass: 239.3538
• Monoisotopic Mass: 239.18852905
• SMILES: C[C@@]12CC[C@@H](C1(C)C)[C@H]([C@H]2O)N1CCOCC1
• Canonical SMILES: O[C@@H]1[C@H](N2CCOCC2)[C@@H]2C([C@@]1(C)CC2)(C)C
• InChI: InChI=1S/C14H25NO2/c1-13(2)10-4-5-14(13,3)12(16)11(10)15-6-8-17-9-7-15/h10-12,16H,4-9H2,1-3H3/t10-,11-,12-,14+/m1/s1
• InChIKey: ZUCSYVYDPCTIJI-BYNQJWBRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3R,4S)-1,7,7-trimethyl-3-(morpholin-4-yl)bicyclo[2.2.1]heptan-2-ol
• IUPAC Traditional name: (1R,2S,3R,4S)-1,7,7-trimethyl-3-(morpholin-4-yl)bicyclo[2.2.1]heptan-2-ol
• Synonyms: [(-)-MIB]; (2S)-3-exo-(Morpholino)isoborneol; (2S)-3-外型-(吗啉)异冰片

Database IDs

• CAS Number: 287105-48-0
• MDL Number: MFCD09265096
• PubChem SID: 162229833; 24885345
• PubChem CID: 11481841

CALCULATED PROPERTIES

• Acid pKa: 14.117538
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.4278748
• LogD (pH = 7.4): 0.31531715
• Log P: 1.4827541
• Molar Refractivity: 67.4001 cm^3
• Polarizability: 27.16556 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 56-65 °C
• Optical Rotation: [α]/D -6°, c = 1 in methanol

Safety Information

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

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C14H25NO2

DETAILS

Sigma Aldrich - 676942

Application
Catalyst for the enantioselective addition of an ethoxy vinyl zinc reagent to aldehydes providing hydroxy vinyl ethers, in turn, easily converted to chiral hydroxy aldehydes.1
Packaging
1 g in glass bottle