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
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About This Item
Empirical Formula (Hill Notation):
C22H30O
CAS Number:
Molecular Weight:
310.47
NACRES:
NA.06
PubChem Substance ID:
UNSPSC Code:
12352112
MDL number:
Quality Segment
assay
97%
form
liquid
optical activity
[α]/D −84±5°, c = 0.5 in chloroform
reaction suitability
reaction type: click chemistry
refractive index
n
functional group
ether, phenyl
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
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
(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.
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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