(R,R)-I-PR-DUPHOS - CAS 136705-65-2

(R,R)-I-PR-DUPHOS is a chiral phosphine ligand for enantioselective synthesis with high yield and high enantioselective results.

Catalog Number

136705-65-2

CAS

136705-65-2

IUPAC Name

(2R,5R)-1-[2-[(2R,5R)-2,5-di(propan-2-yl)phospholan-1-yl]phenyl]-2,5-di(propan-2-yl)phospholane

Synonyms

(R,R)-I-PR-DUPHOS; (+)-1,2-BIS((2R,5R)-2,5-DI-I-PROPYLPHOSPHOLANO)BENZENE; (+)-1,2-BIS[(2R,5R)-2,5-DIISOPROPYLPHOSPHOLANO]BENZENE; BisRRdiipropylphospholanobenzene; (+)-1,2-Bis[(2R, 5R)-2,5-diisopropylphospholano]benzene, Kanata purity; (+)-1,2-Bis((2R,5R)-2,

Molecular Weight

418.58

Molecular Formula

C26H44P2

Product Information

Canonical SMILES

CC(C)C1CCC(P1C2=CC=CC=C2P3C(CCC3C(C)C)C(C)C)C(C)C

InChI

InChI=1S/C26H44P2/c1-17(2)21-13-14-22(18(3)4)27(21)25-11-9-10-12-26(25)28-23(19(5)6)15-16-24(28)20(7)8/h9-12,17-24H,13-16H2,1-8H3/t21-,22-,23-,24-/m1/s1

InChI Key

RBVGOQHQBUPSGX-MOUTVQLLSA-N

Purity

95%

MDL

MFCD02684549

Physical State

Solid

Storage

Inert atmosphere. Room temperature.

Boiling Point

502°C at 760 mmHg

Melting Point

40°C

Flash Point

> 110 °C(230.0 °F)

Optical Activity

+103°( c = 1 in chloroform)

Solubility

Insoluble in water.

Refractive Index

1.5701

TSCA

WGK Germany

Safety Information

Signal Word

Warning

Precautionary Statement

P261 - P280 - P301+P312 - P302+P352 - P305+P351+P338

Hazard Statements

H302 - H315 - H319 - H335

Reference Reading

1.Gold(I) complexes of water-soluble diphos-type ligands: synthesis, anticancer activity, apoptosis and thioredoxin reductase inhibition.

Wetzel C1, Kunz PC, Kassack MU, Hamacher A, Böhler P, Watjen W, Ott I, Rubbiani R, Spingler B. Dalton Trans. 2011 Sep 28;40(36):9212-20. doi: 10.1039/c1dt10368g. Epub 2011 Aug 9.

Gold(I) complexes of imidazole and thiazole-based diphos type ligands were prepared and their potential as chemotherapeutics investigated. Depending on the ligands employed and the reaction conditions complexes [L(AuCl)(2)] and [L(2)Au]X (X = Cl, PF(6)) are obtained. The ligands used are diphosphanes with azoyl substituents R(2)P(CH(2))(2)PR(2) {R = 1-methylimidazol-2-yl (1), 1-methylbenzimidazol-2-yl (4), thiazol-2-yl (5) and benzthiazol-2-yl (6)} as well as the novel ligands RPhP(CH(2))(2)PRPh {R = 1-methylimidazol-2-yl (3)} and R(2)P(CH(2))(3)PR(2) {R = 1-methylimidazol-2-yl (2)}. The cytotoxic activity of the complexes was assessed against three human cancer cell lines and a rat hepatoma cell line and correlated to the lipophilicity of the compounds. The tetrahedral gold complexes [(3)(2)Au]PF(6) and [(5)(2)Au]PF(6) with intermediate lipophilicity (logD(7.4) = 0.21 and 0.25) showed significant cytotoxic activity in different cell lines.

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