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DIPAMP

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From Wikipedia, the free encyclopedia

DIPAMP

Names

Preferred IUPAC name

(Ethane-1,2-diyl)bis[(2-methoxyphenyl)(phenyl)phosphane]

Identifiers

CAS Number

3D model (JSmol)

ChemSpider

2016305
(R,R): 9060243
(S,S): 9594634
(R,S): 9910039

ECHA InfoCard

100.203.286

PubChem CID

2734557
(R,R): 10884975
(S,S): 11419748
(R,S): 11735331

UNII

(R,R): BLJ831OWLW
(S,S): HS6F5EW3U6

CompTox Dashboard(EPA)

DTXSID101027541

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
Key: QKZWXPLBVCKXNQ-UHFFFAOYSA-N
(R,R): 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
Key: QKZWXPLBVCKXNQ-ROJLCIKYSA-N
(S,S): 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
(R,S): 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+
Key: QKZWXPLBVCKXNQ-MEKGRNQZSA-N

SMILES

COc1ccccc1P(CCP(c2ccccc2)c3ccccc3OC)c4ccccc4
(R,R): COc1ccccc1[P@](CC[P@](c2ccccc2)c3ccccc3OC)c4ccccc4
(S,S): COc1ccccc1[P@@](CC[P@@](c2ccccc2)c3ccccc3OC)c4ccccc4
(R,S): O(c1ccccc1[P@@](c2ccccc2)CC[P@@](c3ccccc3)c4ccccc4OC)C

Properties

Chemical formula

C₂₈H₂₈O₂P₂

Molar mass

458.478 g·mol⁻¹

Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).

N verify (what is ^YN ?)

Infobox references

Chemical compound

DIPAMP is anorganophosphorus compound that is used as aligand inhomogeneous catalysis. It is a white solid that dissolves in organic solvents. Work on this compound byW. S. Knowles was recognized with theNobel Prize in Chemistry.^[1] DIPAMP was the basis for one of the first industrial scaleasymmetric hydrogenation, the synthesis of the drugL-DOPA.^[2]

Synthesis of L-DOPA via hydrogenation with theC₂-symmetric diphosphine DIPAMP.

DIPAMP is aC₂-symmetric diphosphine. Eachphosphorus centre, which is pyramidal, bears three different substituents -anisyl, phenyl, and the ethylene group. The ligand therefore exists as the enantiomeric (R,R) and (S,S) pair, as well as the achiralmeso isomer.

DIPAMP was originally prepared by an oxidative coupling, starting from anisyl(phenyl)(methyl)phosphine.

Structure of [Rh(DIPAMP)(cod)]⁺ byX-ray crystallography.^[3]

References

[edit]

^Knowles, William S. (2002). "Asymmetric Hydrogenations (Nobel Lecture) Copyright© The Nobel Foundation 2002. We thank the Nobel Foundation, Stockholm, for permission to print this lecture".Angewandte Chemie International Edition.41 (12): 1998.doi:10.1002/1521-3773(20020617)41:12<1998::AID-ANIE1998>3.0.CO;2-8.
^Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. (1977). "Asymmetric hydrogenation. Rhodium chiral bisphosphine catalyst".Journal of the American Chemical Society.99 (18):5946–5952.Bibcode:1977JAChS..99.5946V.doi:10.1021/ja00460a018.
^H.-J.Drexler; Songlin Zhang; Ailing Sun; A. Spannenberg; A. Arrieta; A. Preetz; D. Heller (2004). "Cationic Rh-bisphosphine-diolefin complexes as precatalysts for enantioselective catalysis––what information do single crystal structures contain regarding product chirality?".Tetrahedron: Asymmetry.15 (14):2139–50.doi:10.1016/j.tetasy.2004.06.036.

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