(1S,4S,8S)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2-methylpropyl)bicyclo[2.2.2]octa-2,5-diene

• ChemBase ID: 135661
• Molecular Formular: C22H30O
• Molecular Mass: 310.473
• Monoisotopic Mass: 310.22966558
• SMILES: CC(C)CC1=C[C@H]2C(=C[C@@]1(C[C@]2(C)OC)C)Cc1ccccc1
• Canonical SMILES: CO[C@@]1(C)C[C@@]2(C)C=C([C@@H]1C=C2CC(C)C)Cc1ccccc1
• InChI: InChI=1S/C22H30O/c1-16(2)11-19-13-20-18(12-17-9-7-6-8-10-17)14-21(19,3)15-22(20,4)23-5/h6-10,13-14,16,20H,11-12,15H2,1-5H3/t20-,21+,22-/m0/s1
• InChIKey: ACWLDJOHMGJACE-BDTNDASRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,8S)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2-methylpropyl)bicyclo[2.2.2]octa-2,5-diene
• IUPAC Traditional name: (1S,4S,8S)-5-benzyl-8-methoxy-1,8-dimethyl-2-(2-methylpropyl)bicyclo[2.2.2]octa-2,5-diene
• Synonyms: (1S,4S,8S)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethyl-2-bicyclo[2.2.2]octa-2,5-diene; (1S,4S,8S) Carreira DOLEFIN Ligand; (1S,4S,8S)--5-Benzyl-8-methoxy-1,8-dimethyl-2-(2′-methylpropyl)-bicyclo[2.2.2]octa-2,5-diene; (1S,4S,8S)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene; (1S,4S,8S) Carreira DOLEFIN 配体; (1S,4S,8S)-5-苄基-2-异丁基-8-甲氧基-1,8-二甲基-2-双环[2.2.2]辛-2,5-二烯; (1S,4S,8S)-5-苄基-8-甲氧基-1,8-二甲基-2-(2′-甲基丙基)-双环[2.2.2]辛-2,5-二烯

Database IDs

• CAS Number: 862499-50-1
• MDL Number: MFCD09265063
• PubChem SID: 24885112; 162229934
• PubChem CID: 12173574

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.2101183
• LogD (pH = 7.4): 5.2101183
• Log P: 5.2101183
• Molar Refractivity: 99.6018 cm^3
• Polarizability: 38.6249 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Refractive Index: n20/D 1.522
• Optical Rotation: [α]/D -84±5°, c = 0.5 in chloroform; [α]20/D -98±5°, c = 0.7 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: ≥98%; 97%
• Optical Purity: enantiomeric ratio: >99:1
• Empirical Formula (Hill Notation): C22H30O

DETAILS

Sigma Aldrich - 672254

Application
When used in conjunction with Rh precatalysts, selectively perform asymmetric conjugate addition to unsaturated esters and aldehydes.1,2
Carreira DOLEFIN Ligands

Sigma Aldrich - 709492

Packaging
100 mg in glass bottle
Application
Carreira DOLEFIN Ligands