[17-(diphenylphosphanyl)-8,12-dioxatricyclo[11.4.0.02,7]heptadeca-1(13),2(7),3,5,14,16-hexaen-3-yl]diphenylphosphane

• ChemBase ID: 141656
• Molecular Formular: C39H32O2P2
• Molecular Mass: 594.617702
• Monoisotopic Mass: 594.18775352
• SMILES: c1ccc(cc1)P(c1ccccc1)c1cccc2c1c1c(cccc1P(c1ccccc1)c1ccccc1)OCCCO2
• Canonical SMILES: C1COc2cccc(c2c2c(OC1)cccc2P(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C39H32O2P2/c1-5-16-30(17-6-1)42(31-18-7-2-8-19-31)36-26-13-24-34-38(36)39-35(41-29-15-28-40-34)25-14-27-37(39)43(32-20-9-3-10-21-32)33-22-11-4-12-23-33/h1-14,16-27H,15,28-29H2
• InChIKey: GTIXSUJKFAATAE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [17-(diphenylphosphanyl)-8,12-dioxatricyclo[11.4.0.0^2,^7]heptadeca-1(13),2(7),3,5,14,16-hexaen-3-yl]diphenylphosphane
• IUPAC Traditional name: [17-(diphenylphosphanyl)-8,12-dioxatricyclo[11.4.0.0^2,^7]heptadeca-1(13),2(7),3,5,14,16-hexaen-3-yl]diphenylphosphane
• Synonyms: (S)-Bis(diphenylphosphino)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin; (S)-C3-TunePhos; (R)-1,13-Bis(diphenylphosphino)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin; (R)-C3-TunePhos; (S)-二(二苯基膦基)-7,8-二氢-6H-二苯并[f,h][1,5]二噁壬英; (R)-(-)-1,13-二(二苯基膦)-7,8-二氢-6H-二苯并[f,h][1,5]二氧杂环壬四烯

Database IDs

• CAS Number: 301847-89-2; 486429-99-6
• MDL Number: MFCD06658115
• PubChem SID: 24883784; 162235890
• PubChem CID: 10722198

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 9.2199
• LogD (pH = 7.4): 9.2199
• Log P: 9.2199
• Molar Refractivity: 178.1468 cm^3
• Polarizability: 71.39727 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 153-161 °C(lit.)
• Optical Rotation: [α]20/D -252±5°, c = 1 in chloroform

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): C39H32O2P2

DETAILS

Sigma Aldrich - 650862

Application
Provides comparable or superior enantioselectivities and catalytic abilities to BINAP in Ru-catalyzed asymmetric hydrogenations of β-keto esters,6 cyclic β-(acylamino)acrylates7 and α-phthalimide ketones.8
Chiral Quest Phosphine Ligands for Asymmetric HydrogenationLigand used in:
• Redox-neutral domino reaction of arylethynylbenzylidenearylpentynones catalyzed by gold catalyst1
• Asymmetric allylic O-alkylation2
• Asymmetric alkylation of racemic secondary phosphines catalyzed by ruthenium chiral diphosphine hydride complexes3
• Stereoselective preparation of cyclopropylcarboxaldehydes via Rh-catalyzed asymmetric hydroformylation of cyclopropenes4
• Rhodium-catalyzed asymmetric hydrogenations5
Packaging
100, 500 mg in glass bottle

Sigma Aldrich - 696064

Application
Provides comparable or superior enantioselectivities and catalytic abilities to BINAP in Ru-catalyzed asymmetric hydrogenations of β-keto esters5, cyclic β-(acylamino)acrylates6 and a-phthalimide ketones7.
Chiral Quest Phosphine Ligands for Asymmetric HydrogenationReactant for:
• Asymmetric hydrogenation of ketones with TunePhos/diamine/ruthenium complexes1
• Stereoselective preparation of arylalkyl esters via enantioselective hydrogenation of enol acetates2Precatalyst for:
• Enantioselective iridium-catalyzed carbonyl allylation from alcohol or aldehyde by transfer hydrogenative coupling of allyl acetate3Catalyst for:
• Enantioselective hydrogenation of a-keto esters to a-hydroxy esters using Ru-tunephos catalysts4
Packaging
100, 500 mg in glass bottle