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709492

Sigma-Aldrich

(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:
862499-50-1
Molecular Weight:
310.47
MDL number:
MFCD09265063
UNSPSC Code:
12352112
PubChem Substance ID:
329762875
NACRES:
NA.06

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

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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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Rhodium-catalyzed enantioselective conjugate addition of organoboronic acids to alpha, beta-unsaturated sulfones
Mauleon P and Carretero JC
Organic Letters, 6(18), 3195-3198 (2004)
(1S,4S,8S)?8?Methoxy?1,8?dimethyl?2?(2?methylpropyl)?5?(phenylmethyl)bicyclo[2.2.2]octa?2,5?diene
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2011)

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