392723

(DHQ)₂PHAL

≥95%

• Synonym(e): Hydrochinin-1,4-phthalazindiyl-diether
• Empirische Formel (Hill-System): C₄₈H₅₄N₆O₄
• CAS-Nummer: 140924-50-1
• Molekulargewicht: 778.98
• Beilstein: 5475677
• MDL-Nummer: MFCD00191975
• UNSPSC-Code: 12352005
• PubChem Substanz-ID: 24864480
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 200
• Assay: ≥95%
• Optische Aktivität: [α]22/D +336°, c = 1.2 in methanol
• mp (Schmelzpunkt): 178 °C (dec.) (lit.)
• SMILES String: CC[C@@H]1CN2CCC1CC2[C@H](Oc3nnc(O[C@@H](C4CC5CCN4C[C@@H]5CC)c6ccnc7ccc(OC)cc67)c8ccccc38)c9ccnc%10ccc(OC)cc9%10
• InChI: 1S/C48H54N6O4/c1-5-29-27-53-21-17-31(29)23-43(53)45(35-15-19-49-41-13-11-33(55-3)25-39(35)41)57-47-37-9-7-8-10-38(37)48(52-51-47)58-46(44-24-32-18-22-54(44)28-30(32)6-2)36-16-20-50-42-14-12-34(56-4)26-40(36)42/h7-16,19-20,25-26,29-32,43-46H,5-6,17-18,21-24,27-28H2,1-4H3/t29-,30+,31-,32+,43-,44-,45-,46-/m1/s1
• InChIKey: YUCBLVFHJWOYDN-PPIALRKJSA-N

Beschreibung

Allgemeine Beschreibung

DHQ)₂PHAL is a modified cinchona alkaloid.

Anwendung

Ligand for Sharpless Asymmetric Dihydroxylation employed in an enantioselective preparation of syn-3,5-hydroxycarboxylates from (E,E)- or (E,Z)-1,3-dienoates.

(DHQ)₂PHAL may be used in the following processes:

• As a catalyst Asymmetric and chemoselective N-allylic alkylation of indoles with Morita-Baylis-Hillman carbonates to form pyrrolo[1,2-a]indole and pyrrolo[3,2,1-ij]quinoline derivatives.
• As a ligand for the osmium catalyzed-Sharpless asymmetric dihydroxylation step of (S)-a-benzoyloxy carboxylic acids multistep synthesis.
• As a ligand for the carbamate based asymmetric aminohydroxylation of styrene derivatives to form N-carbamate protected R-arylglycinols.

Physikalische Form

Asymmetric dihydroxylation of unsaturated esters with trisubstituted C=C bonds.

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H317
• P-Sätze: P280 - P302 + P352
• Gefahreneinstufungen: Skin Sens. 1
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type N95 (US)