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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-dien

97%

Synonym(e):

(1S,4S,8S) Carreira DOLEFIN Ligand, (1S,4S,8S)-8-Methoxy-1,8-dimethyl-2-(2-methylpropyl)-5-(phenylmethyl)-bicyclo[2.2.2]octa-2,5-dien

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About This Item

Empirische Formel (Hill-System):
C22H30O
CAS-Nummer:
862499-50-1
Molekulargewicht:
310.47
MDL-Nummer:
MFCD09265063
UNSPSC-Code:
12352112
PubChem Substanz-ID:
329762875
NACRES:
NA.06

Assay

97%

Form

liquid

Optische Aktivität

[α]/D −84±5°, c = 0.5 in chloroform

Eignung der Reaktion

reaction type: click chemistry

Brechungsindex

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

InChIKey

ACWLDJOHMGJACE-BDTNDASRSA-N

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Allgemeine Beschreibung

(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.

Anwendung

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.

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Die Dokumentenbibliothek aufrufen

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)

Verwandter Inhalt

Carreira Group – Professor Product Portal

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.

Unser Team von Wissenschaftlern verfügt über Erfahrung in allen Forschungsbereichen einschließlich Life Science, Materialwissenschaften, chemischer Synthese, Chromatographie, Analytik und vielen mehr..

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