- DIPAMP
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DIPAMP Ethane-1,2-diylbis[(2-methoxyphenyl)phenylphosphane]Identifiers CAS number 55739-58-7, (R,R)
97858-62-3 (S,S)PubChem 11419748 ChemSpider 9594634 Jmol-3D images Image 1
Image 2- O(c1ccccc1[P@@](c2ccccc2)CC[P@](c3ccccc3)c4ccccc4OC)C
O(c1ccccc1[P@](c2ccccc2)CC[P@@](c3ccccc3)c4ccccc4OC)C
- 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-/m0/s1
Key: QKZWXPLBVCKXNQ-ACHIHNKUSA-N
InChI=1/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
Key: QKZWXPLBVCKXNQ-ROJLCIKYBJ
InChI=1/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-/m0/s1
Key: QKZWXPLBVCKXNQ-ACHIHNKUBV
Properties Molecular formula C28H28O2P2 Molar mass 458.47 g/mol (verify) (what is:
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references DIPAMP is an organophosphorus compound that is used as a ligand in homogeneous catalysis. It is a white solid that dissolves in organic solvents. Work on this compound by W. S. Knowles was recognized with the Nobel Prize in Chemistry.[1] DIPAMP was the basis for of the first practical asymmetric hydrogenation, the synthesis of the drug L-DOPA.
DIPAMP is a chelating diphosphine. Each phosphorus centre, which is pyramidal, bears three different substituents - anisyl, phenyl, and the ethylene group. It therefore exists as the enantiomeric (R,R) and (S,S) pair, as well as the achiral meso isomer.
DIPAMP was originally prepared by an oxidative coupling reaction, starting from anisyl(phenyl)(methyl)phosphine.
Reference
- ^ William S. Knowles "Asymmetric Hydrogenations (Nobel Lecture)" Angewandte Chemie International Edition, 2002, Volume 41, Issue 12, pages 1998–2007. doi:10.1002/1521-3773(20020617)41:12<1998::AID-ANIE1998>3.0.CO;2-8
Categories:- Bisphosphanes
- O(c1ccccc1[P@@](c2ccccc2)CC[P@](c3ccccc3)c4ccccc4OC)C
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