1-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]-4-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]phthalazine

• ChemBase ID: 148351
• Molecular Formular: C48H54N6O4
• Molecular Mass: 778.98016
• Monoisotopic Mass: 778.42065424
• SMILES: CC[C@@H]1CN2CC[C@@H]1C[C@@H]2[C@@H](c1ccnc2c1cc(cc2)OC)Oc1c2ccccc2c(nn1)O[C@H](c1ccnc2c1cc(cc2)OC)[C@H]1C[C@@H]2CCN1C[C@@H]2CC
• Canonical SMILES: CC[C@@H]1CN2CC[C@@H]1C[C@@H]2[C@@H](c1ccnc2c1cc(OC)cc2)Oc1nnc(c2c1cccc2)O[C@H](c1ccnc2c1cc(OC)cc2)[C@H]1C[C@@H]2CCN1C[C@@H]2CC
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]-4-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]phthalazine
• IUPAC Traditional name: 1-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]-4-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]phthalazine
• Synonyms: AD-mix-alpha; AD-mix-α; Hydroquinine 1,4-phthalazinediyl diether; (DHQ)2PHAL; 氢化奎宁 1,4-(2,3-二氮杂萘)二醚

Database IDs

• CAS Number: 140924-50-1
• MDL Number: MFCD00191975
• Beilstein Number: 5475677
• PubChem SID: 24864480; 162242527
• PubChem CID: 51003674

CALCULATED PROPERTIES

• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): 1.6649724
• LogD (pH = 7.4): 4.6111546
• Log P: 8.310911
• Molar Refractivity: 226.5444 cm^3
• Polarizability: 91.92421 Å^3
• Polar Surface Area: 94.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 178 °C (dec.)(lit.)
• Optical Rotation: [α]22/D +336°, c = 1.2 in methanol

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2; 3
• Risk Statements: 22-32-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H317
• GHS Precautionary statements: P261-P305 + P351 + P338; P280
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Supplemental Hazard Statements: Contact with acids liberates very toxic gas.

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C48H54N6O4

DETAILS

Sigma Aldrich - 392758

Components
Mixture contains: (DHQ)2PHAL (Cat. No. 392723) 0.0016 molePotassium carbonate, powder 0.4988 molePotassium ferricyanide 0.4988 molePotassium osmate dihydrate 0.0007 mole
Application
Catalyst employed in the Sharpless Asymmetric Dihyroxylation of (E,E)- or (E,Z)-1,3-dienoates.1 Also used in the preparation of β-hydroxy-γ-lactones from β,γ-unsaturated esters.2
Reagent for Sharpless Asymmetric Dihydroxylation.
General description
Contains chiral ligand (DHQ)2PHAL
Packaging
10, 50 g in glass bottle

Sigma Aldrich - 392723

Application
Ligand for Sharpless Asymmetric Dihydroxylation employed in an enantioselective preparation of syn-3,5-hydroxycarboxylates from (E,E)- or (E,Z)-1,3-dienoates.1
Packaging
500 mg in glass bottle
Legal Information
Sold under license from Shasun Chemicals and Drugs Limited.
Physical form
Asymmetric dihydroxylation of unsaturated esters with trisubstituted C=C bonds.2