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

• ChemBase ID: 141324
• Molecular Formular: C30H48BF4P2Rh
• Molecular Mass: 660.3597548
• Monoisotopic Mass: 660.23154708
• SMILES: [B-](F)(F)(F)F.CC[C@@H]1P([C@H](CC1)CC)c1c(cccc1)P1[C@H](CC[C@@H]1CC)CC.C1C=CCCC=CC1.[Rh+]
• Canonical SMILES: C1CC=CCCC=C1.F[B-](F)(F)F.CC[C@H]1CC[C@@H](P1c1ccccc1P1[C@@H](CC)CC[C@@H]1CC)CC.[Rh+]
• InChI: InChI=1S/C22H36P2.C8H12.BF4.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)5;/h9-12,17-20H,5-8,13-16H2,1-4H3;1-2,7-8H,3-6H2;;/q;;-1;+1/t17-,18-,19-,20-;;;/m0.../s1
• InChIKey: DSYBEQKPSKLNMC-FGOMORKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: λ^1-rhodium(1+) ion (2S,5S)-1-{2-[(2S,5S)-2,5-diethylphospholan-1-yl]phenyl}-2,5-diethylphospholane cycloocta-1,5-diene tetrafluoroboranuide
• 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 tetrafluoroborate
• Synonyms: (S,S)-Et-DUPHOS-Rh; 1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1,2-双[(2S,5S)-2,5-二乙基膦烷基]苯(1,5-环辛二烯)四氟硼酸铑(I)

Database IDs

• CAS Number: 213343-64-7
• PubChem SID: 162235558
• PubChem CID: 11006841

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: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C30H48BF4P2Rh

DETAILS

Sigma Aldrich - 698385

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:
• Preparation of a key unit B precursor of cryptophycins via Horner-Wadsworth-Emmons reaction and asymmetric hydrogenation1
• Preparation of constrained phenylalanine analogs via Heck reaction followed by asymmetric hydrogenation and cyclization steps2
• Enantioselective preparation of N-benzyloxy-β-amino acid Me esters by hydrogenation of α-(benzyloxyaminomethyl)acrylate stereoisomers3
• Preparation of fluoro amino acids as synthons for potent macrocyclic HCV NS3 protease inhibitors4
• Stereoselective preparation of triply isotope-labeled Ser, Cys, and Ala5
• Preparation of β-amino acids from asymmetric hydrogenation of α-(aminomethyl)acrylates6
• Asymmetric hydrogenation of a-primary and secondary amino ketones and asymmetric synthesis of (-)-arbutamine and (-)-denopamine7