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1,2-Bis[(2R,5R)-2,5-dimethylphospholano]ethane

Catalog Number
ACM129648073-2
Product Name
1,2-Bis[(2R,5R)-2,5-dimethylphospholano]ethane
Structure
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CAS
129648-07-3
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Synonyms
Phospholane, 1,1'-(1,2-ethanediyl)bis(2,5-dimethyl-, (2R,2'R,5R,5'R)-; (+)-1,2-Bis(2R,5R)-2,5-dimethylphospholano)ethane; MFCD01073770; 1,2-Bis((2R,5R)-2,5-dimethylphospholan-1-yl)ethane; SCHEMBL3688560; ZINC2572357; Me-bpe, (R,R)-; (R,R)-Me-bpe, (+)-; (S,S)-Me-en-duphos; 1,2-Bis[(2R,5R)-2,5-dimethyl-1-phospholanyl]ethane;
IUPAC Name
(2R,5R)-1-[2-[(2R,5R)-2,5-dimethylphospholan-1-yl]ethyl]-2,5-dimethylphospholane;
Molecular Weight
258.326g/mol
Molecular Formula
C14H28P2;
Canonical SMILES
CC1CCC(P1CCP2C(CCC2C)C)C;
InChI
InChI=1S/C14H28P2/c1-11-5-6-12(2)15(11)9-10-16-13(3)7-8-14(16)4/h11-14H,5-10H2,1-4H3/t11-,12-,13-,14-/m1/s1;
InChI Key
IRCDUOCGSIGEAI-AAVRWANBSA-N;
Complexity
185
Covalently-Bonded Unit Count
1
Defined Atom Stereocenter Count
4
Exact Mass
258.167g/mol
Heavy Atom Count
16
Monoisotopic Mass
258.167g/mol
Rotatable Bond Count
3
Topological Polar Surface Area
0A^2
UNII
1LS1AFH1F1
Application
1,2-Bis[(2R,5R)-2,5-dimethylphospholano]ethane, a clear colorless oily liquid, serves as an efficient ligand within the DUPHOS family of catalysts. It is highly effective for the asymmetric hydrogenation of a range of chemical compounds, including various substituted acetamidoacrylates and enol acetates, as well as tetrasubstituted enamides. The use of this product results in the formation of hydrogenated products with high enantiomeric excesses, making it invaluable in applications requiring precise chiral synthesis.
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