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

• ChemBase ID: 141321
• 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-;;;/m0.../s1
• InChIKey: HZLILTNLWVOBFS-FGOMORKPSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: λ^1-rhodium(1+) ion (1Z,5Z)-cycloocta-1,5-diene (2S,5S)-1-{2-[(2S,5S)-2,5-diethylphospholan-1-yl]phenyl}-2,5-diethylphospholane trifluoromethanesulfonate; λ^1-rhodium(1+) ion (2S,5S)-1-{2-[(2S,5S)-2,5-diethylphospholan-1-yl]phenyl}-2,5-diethylphospholane cycloocta-1,5-diene trifluoromethanesulfonate
• IUPAC Traditional name: λ^1-rhodium(1+) ion (2S,5S)-1-{2-[(2S,5S)-2,5-diethylphospholan-1-yl]phenyl}-2,5-diethylphospholane 1,5-cyclooctadiene, (Z,Z)- triflate; λ^1-rhodium(1+) ion (2S,5S)-1-{2-[(2S,5S)-2,5-diethylphospholan-1-yl]phenyl}-2,5-diethylphospholane 1,5-cyclooctadiene triflate
• Synonyms: (+)-1,2-Bis((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (S,S)-Et-DUPHOS-Rh; 1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (+)-1,2-双((2S,5S)-2,5-二乙基膦)苯(环辛二烯)三氟甲磺酸铑(I); 1,2-双[(2S,5S)-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: 142184-30-3
• MDL Number: MFCD00269861
• PubChem SID: 162235555
• PubChem CID: 11146978

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

Physical Property

• Apperance: Crystalline, Packaged under argon

Safety Information

• Storage Warning: Air & Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• TSCA Listed: 否
• 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 - 698407

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 involved in:
• Oxidation of the δ-position via ruthenium catalysis1
• Stereoselective hydrogenation reactions of dehydroamino acid esters2 and macrocyclic peptideomimetics3
• Synthesis of cyclopeptide alkaloid mucronine E4, fluoro-containing amino acids5, and labeled protease inhibitors6