709492

(1S,4S,8S)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene

97%

• Synonym(s): (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-dimethyl-2-bicyclo[2.2.2]octa-2,5-diene
• Empirical Formula (Hill Notation): C₂₂H₃₀O
• CAS Number: 862499-50-1
• Molecular Weight: 310.47
• MDL number: MFCD09265063
• UNSPSC Code: 12352112
• PubChem Substance ID: 329762875
• NACRES: NA.06

Properties

• Assay: 97%
• form: liquid
• optical activity: [α]/D −84±5°, c = 0.5 in chloroform
• reaction suitability: reaction type: click chemistry
• refractive index: n20/D 1.522
• SMILES string: CO[C@@]1(C)C[C@@]2(C)C=C(Cc3ccccc3)[C@@H]1C=C2CC(C)C
• 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
• InChI key: ACWLDJOHMGJACE-BDTNDASRSA-N

Description

General description

(1S,4S,8S)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene, an enantiopure diene ligand developed by Carreira, is most commonly used in asymmetric catalysis. It is generally prepared from commercially available (R)-carvone.

Application

Carreira DOLEFIN Ligands

(1S,4S,8S)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene is mainly useful for the stereoselective synthesis of diarylmethine stereogenic centers.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable