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

• ChemBase ID: 148059
• 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-/m0/s1
• InChIKey: YUCBLVFHJWOYDN-HVLQGHBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-bis[(S)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]phthalazine
• IUPAC Traditional name: 1,4-bis[(S)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]phthalazine
• Synonyms: Hydroquinidine 1,4-phthalazinediyl diether; (DHQD)2PHAL; AD-mix-beta; AD-mix-β; 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚

Database IDs

• CAS Number: 140853-10-7
• MDL Number: MFCD00198107
• Beilstein Number: 5475678
• PubChem SID: 24864481; 162242238
• PubChem CID: 11217202

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: 160 °C (dec.)(lit.)
• Optical Rotation: [α]22/D -262°, 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
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, 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 - 392731

Application
Ligand for Sharpless Asymmetric Dihydroxylation.
Ligand for the Sharpless Asymmetric Dihydroylxation recently used in a study of the hydroxylation of a steroidal dienic side chain.
Packaging
1 g in glass bottle
Legal Information
Sold under license from Rhodia Pharma Solutions.

Sigma Aldrich - 392766

Components
Mixture contains:(DHQD)2PHAL (Cat. No. 392731) 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 (DHQD)2PHAL
Packaging
10 g in glass bottle
50 g in poly bottle
Legal Information
Sold under license from Rhodia Pharma Solutions.