CAS 147253-67-6 1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene

Synonyms

(R,R)-1,2-Bis(2,5-dimethylphospholano)benzene; DTXSID20163641; (-)-1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene, kanata purity; H5W03D1HAQ; UNII-H5W03D1HAQ; (R,R)-Me-DUPHOS; AJNZWRKTWQLAJK-KLHDSHLOSA-N; (+)-1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene; (-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene; (-)-1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene, >=95.0%;

IUPAC Name

(2R,5R)-1-[2-[(2R,5R)-2,5-dimethylphospholan-1-yl]phenyl]-2,5-dimethylphospholane;

Molecular Weight

306.37g/mol

Molecular Formula

C18H28P2;

Canonical SMILES

CC1CCC(P1C2=CC=CC=C2P3C(CCC3C)C)C;

InChI

InChI=1S/C18H28P2/c1-13-9-10-14(2)19(13)17-7-5-6-8-18(17)20-15(3)11-12-16(20)4/h5-8,13-16H,9-12H2,1-4H3/t13-,14-,15-,16-/m1/s1;

InChI Key

AJNZWRKTWQLAJK-KLHDSHLOSA-N;

Complexity

277

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

EC Number

604-579-6

Exact Mass

306.167g/mol

Heavy Atom Count

Monoisotopic Mass

306.167g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

UNII

H5W03D1HAQ

Application

1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene is a versatile and critical compound utilized in various fields such as organic synthesis, pharmaceuticals, agrochemicals, and dyestuffs. Its primary role is as a highly effective ligand within the DUPHOS family of catalysts, enabling exceptional efficiencies in asymmetric hydrogenation reactions. It facilitates the conversion of numerous substrates, including substituted cetamidoacrylates, enol acetates, imines, enamines, enamides, vinyl alcohols, enol phosphonates, and allylic alcohols, into products with high enantiomeric excess. Additionally, this ligand supports catalytic processes such as asymmetric [4+1] cycloadditions of vinylallenes with CO, Rh-catalyzed enyne cycloisomerizations, and the catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines, demonstrating its broad applicability and essential role in advancing chemical synthesis methods.

February 2, 2025

A Remarkable Catalyst for Asymmetric Hydrogenation

The 1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene from Alfa Chemistry greatly enhanced our research. Utilized in vinyl alcohol hydrogenation, it delivered exceptional enantiomeric excess and reliability, improving efficiency in enol acetate transformations.