DIPAMP

DIPAMP
Names
Preferred IUPAC name
(Ethane-1,2-diyl)bis[(2-methoxyphenyl)(phenyl)phosphane]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.203.286 Edit this at Wikidata
UNII
  • 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
  • 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
C28H28O2P2
Molar mass 458.478 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 one of the first industrial scale asymmetric hydrogenation, the synthesis of the drug L-DOPA.[2]

Synthesis of L-DOPA via hydrogenation with the C2-symmetric diphosphine DIPAMP.

DIPAMP is a C2-symmetric diphosphine. Each phosphorus 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 achiral meso isomer.

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

Structure of [Rh(DIPAMP)(cod)]+ by X-ray crystallography.[3]

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.