[(2R,4R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]methanol

• ChemBase ID: 145846
• Molecular Formular: C10H17NO
• Molecular Mass: 167.24808
• Monoisotopic Mass: 167.13101417
• SMILES: C=C[C@H]1CN2CC[C@@H]1C[C@@H]2CO
• Canonical SMILES: OC[C@H]1C[C@H]2CCN1C[C@@H]2C=C
• InChI: InChI=1S/C10H17NO/c1-2-8-6-11-4-3-9(8)5-10(11)7-12/h2,8-10,12H,1,3-7H2/t8-,9+,10+/m0/s1
• InChIKey: GAFZBOMPQVRGKU-IVZWLZJFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,4R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]methanol
• IUPAC Traditional name: [(2R,4R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]methanol
• Synonyms: (2R,5R)-(+)-5-Vinyl-2-quinuclidinemethanol; (2R,5R)-(+)-5-乙烯基-2-奎宁环甲醇

Database IDs

• MDL Number: MFCD01321270
• PubChem SID: 24870808; 162240047
• PubChem CID: 71311191

CALCULATED PROPERTIES

• Acid pKa: 15.112198
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -2.6805568
• LogD (pH = 7.4): -1.4811612
• Log P: 0.72924036
• Molar Refractivity: 50.0263 cm^3
• Polarizability: 19.598059 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 267 °C(lit.)
• Flash Point: 112 °C; 233.6 °F
• Density: 1.073 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.515(lit.)
• Optical Rotation: [α]20/D +189°, c = 1 in methanol

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C10H17NO

DETAILS

Sigma Aldrich - 472549

Packaging
250 mg in glass bottle
Application
Valuable building block for medicinal chemistry. The skeleton of this compound is identical to the framework of cinchona alkaloids. Possible applications include resolving agents, chiral stationary phases,1 and chiral ligands in asymmetric synthesis.2