2-[(1R,4R,7R)-5-methyl-7-(propan-2-yl)bicyclo[2.2.2]octa-2,5-dien-2-yl]propan-2-ol

• ChemBase ID: 143446
• Molecular Formular: C15H24O
• Molecular Mass: 220.35046
• Monoisotopic Mass: 220.18271539
• SMILES: CC1=C[C@H]2[C@H](C[C@@H]1C=C2C(C)(C)O)C(C)C
• Canonical SMILES: CC([C@H]1C[C@@H]2C=C([C@H]1C=C2C)C(O)(C)C)C
• InChI: InChI=1S/C15H24O/c1-9(2)12-7-11-8-14(15(4,5)16)13(12)6-10(11)3/h6,8-9,11-13,16H,7H2,1-5H3/t11-,12-,13+/m1/s1
• InChIKey: NDYITPSGAZLHSH-UPJWGTAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,4R,7R)-5-methyl-7-(propan-2-yl)bicyclo[2.2.2]octa-2,5-dien-2-yl]propan-2-ol
• IUPAC Traditional name: 2-[(1R,4R,7R)-7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-dien-2-yl]propan-2-ol
• Synonyms: (1R,4R,7R)-α,α,5-Trimethyl-7-(1-methylethyl)bicyclo[2.2.2]octa-2,5-diene-2-methanol; (1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene; (1R,4R,7R)-α,α,5-三甲基-7-(1-甲基乙基)二环[2.2.2]辛-2,5-二烯-2-甲醇; (1R,4R,7R)-7-异丙基-2-(1-羟基-1-甲基乙基)-5-甲基二环[2.2.2]辛-2,5-二烯

Database IDs

• CAS Number: 1063949-39-2
• MDL Number: MFCD16876054
• PubChem SID: 162237665
• PubChem CID: 25108316

CALCULATED PROPERTIES

• Acid pKa: 18.77251
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.9755907
• LogD (pH = 7.4): 2.975591
• Log P: 2.975591
• Molar Refractivity: 70.2281 cm^3
• Polarizability: 27.066486 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Density: 0.952 g/mL at 25 °C
• Refractive Index: n20/D 1.495
• Optical Rotation: [α]22/D +42.0°, c = 0.5 in chloroform

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H400
• GHS Precautionary statements: P273
• RID/ADR: UN 3077 9/PG 3

Product Information

• Empirical Formula (Hill Notation): C15H24O

DETAILS

Sigma Aldrich - 723673

Packaging
1 g in glass bottle
Application
Reactant for:
• Chiral ligand for asymmetric 1,4-conjugate addition1Used for:
• Rh-catalyzed asymmetric conjugate addition reaction of boronic acids to α,β-unsaturated ketones2
• Rhodium-catalyzed asymmetric arylation of imines3