392723

(DHQ)₂PHAL

≥95%

• Synonym(s): Hydroquinine 1,4-phthalazinediyl diether
• Empirical Formula (Hill Notation): C₄₈H₅₄N₆O₄
• CAS Number: 140924-50-1
• Molecular Weight: 778.98
• Beilstein/REAXYS Number: 5475677
• MDL number: MFCD00191975
• UNSPSC Code: 12352005
• PubChem Substance ID: 24864480
• NACRES: NA.22

Properties

• Quality Level: 200
• assay: ≥95%
• optical activity: [α]22/D +336°, c = 1.2 in methanol
• mp: 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
• InChI key: YUCBLVFHJWOYDN-PPIALRKJSA-N

Description

General description

DHQ)₂PHAL is a modified cinchona alkaloid.

Application

(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.

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

Physical form

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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H317
• pcodes: P280 - P302 + P352
• Hazard Classifications: Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type N95 (US)