{1-[2-(diphenylphosphanyl)-5,6,7,8-tetrahydronaphthalen-1-yl]-5,6,7,8-tetrahydronaphthalen-2-yl}diphenylphosphane

• ChemBase ID: 140888
• Molecular Formular: C44H40P2
• Molecular Mass: 630.735922
• Monoisotopic Mass: 630.26052454
• SMILES: c1ccc(cc1)P(c1ccccc1)c1ccc2c(c1c1c(ccc3c1CCCC3)P(c1ccccc1)c1ccccc1)CCCC2
• Canonical SMILES: c1ccc(cc1)P(c1ccc2c(c1c1c3CCCCc3ccc1P(c1ccccc1)c1ccccc1)CCCC2)c1ccccc1
• InChI: InChI=1S/C44H40P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-12,19-26,29-32H,13-18,27-28H2
• InChIKey: ANSOKCGDSQQISA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {1-[2-(diphenylphosphanyl)-5,6,7,8-tetrahydronaphthalen-1-yl]-5,6,7,8-tetrahydronaphthalen-2-yl}diphenylphosphane
• IUPAC Traditional name: {1-[2-(diphenylphosphanyl)-5,6,7,8-tetrahydronaphthalen-1-yl]-5,6,7,8-tetrahydronaphthalen-2-yl}diphenylphosphane
• Synonyms: (R)-(+)-2,2′-Bis(diphenylphospino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl; [(1R)-5,5′,6,6′,7,7′,8,8′-octahydro-[1,1′-binaphthalene]-2,2′-diyl]bis[diphenylphosphine]; (R)-H8-BINAP; (S)-(-)-2,2′-Bis(diphenylphospino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl; [(1S)-5,5′,6,6′,7,7′,8,8′-octahydro-[1,1′-binaphthalene]-2,2′-diyl]bis[diphenylphosphine]; (S)-H8-BINAP; (R)-(+)-2,2′-双(二苯基膦)-5,5′,6,6′,7,7′,8,8′-八氢-1,1′-联萘; [(1R)-5,5′,6,6′,7,7′,8,8′-八氢-[1,1′-联萘]-2,2′-二基]双[二苯基膦]; (S)-(-)-2,2′-2,2′-双(二苯基膦)-5,5′,6,6′,7,7′,8,8′-八氢-1,1′-联萘; [(1S)-5,5′,6,6′,7,7′,8,8′-八氢-[1,1′-联萘]-2,2′-二基]双[二苯基膦]

Database IDs

• CAS Number: 139139-86-9; 139139-93-8
• MDL Number: MFCD01630795
• PubChem SID: 162235126
• PubChem CID: 4366894

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 12.297
• LogD (pH = 7.4): 12.297
• Log P: 12.297
• Molar Refractivity: 197.2884 cm^3
• Polarizability: 78.32092 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +74°, c = 0.5 in toluene

Product Information

• Purity: ≥94%
• Grade: technical grade
• Empirical Formula (Hill Notation): C44H40P2

DETAILS

Sigma Aldrich - 693014

Packaging
50, 100 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only.
Application
Takasago Ligands and Complexes for Asymmetric Reactions

Sigma Aldrich - 692387

Packaging
50, 100 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only.
Application
Takasago Ligands and Complexes for Asymmetric Reactions
Catalytic ligand used for:
• Enantioselective synthesis of dihydrobenzofurans and dihydronaphthofurans via olefin isomerization/enantioselective intramolecular Alder-ene reaction of enynes catalyzed by Rh
• Preparation of axially chiral biaryl compounds by gold-catalyzed stereoselective intramolecular hydroarylation
• Preparation of chiral 3-alkyl-substituted indolines by tandem condensation-asymmetric hydrogenation of indoles with aldehydes, catalyzed by Bronsted acids and palladium BINAP complexes
• Stereoselective preparation of hydrindanes and decalins containing up to four contiguous stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of ene-allenes with allenes
• Rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes
• Stereoselective preparation of 2,3-substituted indolines via Pd-catalyzed hydrogenation of (α-hydroxyalkyl)indoles