CAS 55739-58-7 (R,R)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane

Synonyms

(-)-DIPAMP; UNII-BLJ831OWLW; B3035; ST24036671; (S,S)-Ethylenebis[(2-methoxyphenyl)phenylphosphine]; AKOS008901415; OR310818; (R,R)-(-)-1,2-Bis[2-methoxyphenyl)(phenyl)phosphino]ethane; GS-0006; (R,R)-DIPAMP;

IUPAC Name

(R)-(2-methoxyphenyl)-[2-[(2-methoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane;

Molecular Weight

458.478g/mol

Molecular Formula

C28H28O2P2;

Canonical SMILES

COC1=CC=CC=C1P(CCP(C2=CC=CC=C2)C3=CC=CC=C3OC)C4=CC=CC=C4;

InChI

InChI=1S/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32-/m1/s1;

InChI Key

QKZWXPLBVCKXNQ-ROJLCIKYSA-N;

Complexity

472

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

458.156g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

458.156g/mol

Rotatable Bond Count

Topological Polar Surface Area

18.5A^2

UNII

BLJ831OWLW

Application

(R,R)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane serves as an essential component in the field of chemical synthesis, particularly in the creation of rhodium diphosphine trinuclear complexes. This compound is primarily utilized for its ability to catalyze reactions with high enantioselectivity and activity. As a critical reactant, it facilitates the asymmetric hydrogenation of enamides, enol acetates, and olefins. Furthermore, (R,R)-1,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane is instrumental in the enantioselective [3+2] cycloaddition of γ-substituted allenoates with β-perfluoroalkyl enones, as well as 3-butynoates with electron-deficient olefins, ultimately yielding substituted cyclopentenes. Its role in these processes not only highlights its versatility but also underscores its importance in advancing asymmetric synthesis methodologies.

April 8, 2025

Excellent Catalyst for Asymmetric Hydrogenation in Research

The white crystalline powder of (R,R)-DIPAMP proved essential in preparing Rhodium complexes. It exhibited remarkable enantioselectivity in asymmetric hydrogenation of olefins, enhancing our research outcomes significantly. Highly recommend for catalytic applications.