1,4-bis[(S)-[(2R,4S,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]-9,10-dihydroanthracene-9,10-dione

• ChemBase ID: 149539
• Molecular Formular: C54H56N4O6
• Molecular Mass: 857.04564
• Monoisotopic Mass: 856.41998553
• SMILES: CC[C@@H]1CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cc(cc2)OC)Oc1ccc(c2c1C(=O)c1ccccc1C2=O)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)Oc1ccc(c2c1C(=O)c1ccccc1C2=O)O[C@@H](c1ccnc2c1cc(OC)cc2)[C@H]1C[C@@H]2CCN1C[C@H]2CC
• InChI: InChI=1S/C54H56N4O6/c1-5-31-29-57-23-19-33(31)25-45(57)53(39-17-21-55-43-13-11-35(61-3)27-41(39)43)63-47-15-16-48(50-49(47)51(59)37-9-7-8-10-38(37)52(50)60)64-54(46-26-34-20-24-58(46)30-32(34)6-2)40-18-22-56-44-14-12-36(62-4)28-42(40)44/h7-18,21-22,27-28,31-34,45-46,53-54H,5-6,19-20,23-26,29-30H2,1-4H3/t31-,32-,33+,34+,45-,46-,53+,54+/m1/s1
• InChIKey: ARCFYUDCVYJQRN-ZPCQJLRDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-bis[(S)-[(2R,4S,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: 1,4-bis[(S)-[(2R,4S,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]anthracene-9,10-dione
• Synonyms: Hydroquinidine (anthraquinone-1,4-diyl) diether; (DHQD)2AQN; 氢化奎尼丁(蒽醌-1,4-二基)二醚

Database IDs

• CAS Number: 176298-44-5
• MDL Number: MFCD00467216
• PubChem SID: 162243704
• PubChem CID: 71311419

CALCULATED PROPERTIES

• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): 5.0624204
• LogD (pH = 7.4): 8.442632
• Log P: 9.275421
• Molar Refractivity: 246.8538 cm^3
• Polarizability: 99.1259 Å^3
• Polar Surface Area: 103.32 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 165 °C(lit.)
• Optical Rotation: [α]/D -498°

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C54H56N4O6

DETAILS

Sigma Aldrich - 456713

Application
Superior ligand for asymmetric dihydroxylation reactions of most olefins bearing aliphatic substituents or olefins having heteroatoms in the allylic position.1
Packaging
500 mg in glass bottle
Legal Information
Sold under license from Rhodia Pharma Solutions.