(1R)-2-tert-butyl-1-[(1R)-2-tert-butyl-2,3-dihydro-1H-isophosphindol-1-yl]-2,3-dihydro-1H-isophosphindole

• ChemBase ID: 142573
• Molecular Formular: C24H32P2
• Molecular Mass: 382.458402
• Monoisotopic Mass: 382.19792428
• SMILES: CC(C)(C)P1Cc2ccccc2[C@@H]1[C@H]1c2ccccc2CP1C(C)(C)C
• Canonical SMILES: CC(P1Cc2c([C@@H]1[C@H]1c3ccccc3CP1C(C)(C)C)cccc2)(C)C
• InChI: InChI=1S/C24H32P2/c1-23(2,3)25-15-17-11-7-9-13-19(17)21(25)22-20-14-10-8-12-18(20)16-26(22)24(4,5)6/h7-14,21-22H,15-16H2,1-6H3/t21-,22-,25?,26?/m1/s1
• InChIKey: HCBRTCFUVLYSKU-URFUVCHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-2-tert-butyl-1-[(1R)-2-tert-butyl-2,3-dihydro-1H-isophosphindol-1-yl]-2,3-dihydro-1H-isophosphindole
• IUPAC Traditional name: (1R)-2-tert-butyl-1-[(1R)-2-tert-butyl-1,3-dihydroisophosphindol-1-yl]-1,3-dihydroisophosphindole
• Synonyms: (1R,1′R,2S,2′S)-2,2′-Di-tert-butyl-2,3,2′,3′-tetrahydro-1H,1′H-(1,1′)biisophosphindolyl; (1R,1′R,2S,2′S)-DuanPhos; (1R,1′R,2S,2′S)-2,2′-二叔丁基-2,3,2′,3′-四氢-1H,1′H-(1,1′)二异磷哚

Database IDs

• CAS Number: 528814-26-8
• PubChem SID: 24884305; 162236800
• PubChem CID: 45052233

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.3000956
• LogD (pH = 7.4): 5.328805
• Log P: 5.3292
• Molar Refractivity: 125.3762 cm^3
• Polarizability: 46.059456 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 214-246 °C
• Optical Rotation: [α]20/D +18°, c = 1 in chloroform

Safety Information

• German water hazard class: 3

Product Information

• Empirical Formula (Hill Notation): C24H32P2

DETAILS

Sigma Aldrich - 657697

Packaging
100, 500 mg in glass bottle
Application
Chiral Quest Phosphine Ligands for Asymmetric HydrogenationCatalytic ligand used for:
• Stereoselective synthesis of cyano-substituted dihydropyrroles by annulation of cyanoallenes1
• Rhodium-catalyzed intermolecular enantioselective hydroacylation of alkynes to give alpha- and beta-substituted unsaturated ketones by kinetic resolution2
• Stereoselective preparation of β-amino nitriles via rhodium-catalyzed asymmetric hydrogenation of amino acrylonitriles3
• Stereoselective preparation of anti-1,3-amino alcohols via rhodium-catalyzed asymmetric hydrogenation of β-ketoenamide intermediates4
• Stereoselective preparation of acetylaminoindane via rhodium-catalyzed asymmetric hydrogenation of acetylaminoindene5