λ1-rhodium(1+) ion (2R,5R)-1-{2-[(2R,5R)-2,5-diethylphospholan-1-yl]phenyl}-2,5-diethylphospholane cycloocta-1,5-diene trifluoromethanesulfonate

• ChemBase ID: 141322
• Molecular Formular: C31H48F3O3P2RhS
• Molecular Mass: 722.6242516
• Monoisotopic Mass: 722.18065332
• SMILES: CC[C@H]1P([C@@H](CC1)CC)c1c(cccc1)P1[C@@H](CC[C@H]1CC)CC.C1C=CCCC=CC1.C(S(=O)(=O)[O-])(F)(F)F.[Rh+]
• Canonical SMILES: C1CC=CCCC=C1.FC(S(=O)(=O)[O-])(F)F.CC[C@@H]1CC[C@H](P1c1ccccc1P1[C@H](CC)CC[C@H]1CC)CC.[Rh+]
• InChI: InChI=1S/C22H36P2.C8H12.CHF3O3S.Rh/c1-5-17-13-14-18(6-2)23(17)21-11-9-10-12-22(21)24-19(7-3)15-16-20(24)8-4;1-2-4-6-8-7-5-3-1;2-1(3,4)8(5,6)7;/h9-12,17-20H,5-8,13-16H2,1-4H3;1-2,7-8H,3-6H2;(H,5,6,7);/q;;;+1/p-1/t17-,18-,19-,20-;;;/m1.../s1
• InChIKey: HZLILTNLWVOBFS-QFNVKMGQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: λ^1-rhodium(1+) ion (2R,5R)-1-{2-[(2R,5R)-2,5-diethylphospholan-1-yl]phenyl}-2,5-diethylphospholane cycloocta-1,5-diene trifluoromethanesulfonate
• IUPAC Traditional name: λ^1-rhodium(1+) ion (2R,5R)-1-{2-[(2R,5R)-2,5-diethylphospholan-1-yl]phenyl}-2,5-diethylphospholane 1,5-cyclooctadiene triflate
• Synonyms: (R,R)-Et-DUPHOS-Rh; 1,2-Bis[(2R,5R)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; 1,2-双[(2R,5R)-2,5-二乙基膦烷基]苯(1,5-环辛二烯)三氟甲磺酸铑(I)

Database IDs

• CAS Number: 136705-77-6
• MDL Number: MFCD00269860
• PubChem SID: 162235556
• PubChem CID: 5702639

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.78217
• LogD (pH = 7.4): 6.0301037
• Log P: 6.0478
• Molar Refractivity: 108.7338 cm^3
• Polarizability: 43.824978 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

• Empirical Formula (Hill Notation): C31H48F3O3P2RhS

DETAILS

Sigma Aldrich - 698393

Packaging
50, 250 mg in glass bottle
Legal Information
Sold in collaboration with Kanata Chemical Technologies Inc. for research purposes only. These compounds were made and sold under license from E.I. du Pont de Nemours and Company, which license does not include the right to use the compounds in producing products for sale in the pharmaceutical field.
Application
DuPhos and BPE Ligands: Highly Efficient Privileged LigandsCatalyst for:
• Stereoselective synthesis of δ-amino acid derivatives via asymmetric hydrogenation of acetylaminopentenoic acid derivatives1
• Stereoselective synthesis of manzacidins A and C via stereoselective hydrogenation2
• Stereoselective synthesis of tetracyclic core of manzamine A via Rh-catalyzed asymmetric hydrogenation, diastereoselective Diels-Alder reaction, Eschenmoser-Tanabe fragmentation, Chang′s amide formation, and Hofmann rearrangement3
• Asymmetric preparation of chiral Cbz-aminodifluorobutyric acid Me ester and its analogs4
• Biphasic catalytic hydrogenations in ionic liquids with addition of water as a second solvent5
• Preparation of cyclobutane-containing amino acids via asymmetric hydrogenations of cyclobutyl enamides6
• Asymmetric preparation of both enantiomers of (dimethoxycoumaryl)alanine as suitable fluorescent peptide labels7