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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%

Sinónimos:

(1S,4S,8S) Carreira DOLEFIN Ligand

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About This Item

Fórmula empírica (notación de Hill):
C22H30O
Número de CAS:
862499-50-1
Peso molecular:
310.47
MDL number:
MFCD09265063
UNSPSC Code:
12352112
PubChem Substance ID:
329762875
NACRES:
NA.06

Quality Level

100

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

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

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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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
MKBQ6832V
MKBC2105

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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)

Contenido relacionado

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The Carreira Research Group is focused on expanding and creating access to uncharted landscape in chemical space. In joint efforts with SpiroChem, Carreira develops innovative spirocyclic building blocks, seeking to make them available to the community at large. Molecules constructed from these building blocks take on unique three-dimensional profiles due to the underlying spirocyclic scaffold, enriched by the presence of diverse combinations of exit vectors as sites for functionalization. Importantly, the spirocyclic building blocks possess physicochemical properties useful in the drug discovery process. Thus, drug leads can be tuned through appending these subunits to the periphery of a given scaffold. Moreover, these compact modules represent a useful collection of unprecedented inputs for fragment-based libraries. In all applications, the inherent novelty of the structure affords researchers new opportunities to run wild in their designs and avenues to chemical space – with their imagination as the sole limitations. We are proud to partner in the efforts to make these building blocks widely available.

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