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Merck

682144

Sigma-Aldrich

(R)-(–)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane

96%

Sinónimos:

(R)-Phanephos

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About This Item

Fórmula empírica (notación de Hill):
C40H34P2
Número de CAS:
Peso molecular:
576.65
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

assay

96%

form

solid

optical activity

[α]/D -34±4°, c = 1 in chloroform

mp

222-226 °C

InChI

1S/C40H34P2/c1-5-13-35(14-6-1)41(36-15-7-2-8-16-36)39-29-31-21-25-33(39)27-23-32-22-26-34(28-24-31)40(30-32)42(37-17-9-3-10-18-37)38-19-11-4-12-20-38/h1-22,25-26,29-30H,23-24,27-28H2

Inchi Key

GYZZZILPVUYAFJ-UHFFFAOYSA-N

Application

(R)-(-)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane may be used as a ligand in the following processes:
  • Enantioselective reductive cyclization of 1,6-enynes via asymmetric hydrogenation in the presence of a rhodium catalyst to form alkylidene-substituted heterocycles.
  • Asymmetric hydroboration of 3,3-disubstituted cyclopropenes to form 2,2-disubstituted cyclopropyl boronates.
  • Asymmetric ring-opening reactions of azabenzonorbornadienes in the presence of zinc(II) triflate and palladium(II) acetate to form aminodihydronaphthalenes.
Efficient ligand for asymmetric hydrogentation of dehydroamino acids, methyl esters and keytones.

Legal Information

Sold in collaboration with Johnson Matthey Catalyst for research purposes only. US5874629 and any patents arising therefrom apply.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificados de análisis (COA)

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Enantioselective Reductive Cyclization of 1, 6-Enynes via Rhodium-Catalyzed Asymmetric Hydrogenation: C- C Bond Formation Precedes Hydrogen Activation.
Jang HY, et al.
Journal of the American Chemical Society, 127(17), 6174-6175 (2005)
Catalytic enantioselective hydroboration of cyclopropenes.
Rubina M, et al.
Journal of the American Chemical Society, 125(24), 7198-7199 (2003)
[2.2] Paracyclophane Derivatives: Synthesis and Application in Catalysis
Paradies, Jan
Synthesis, 2011.23, 3749-3766 (2011)
Highly efficient ruthenium-catalyzed oxime to amide rearrangement
Owston, Nathan A., Alexandra J. Parker, and Jonathan MJ Williams
Organic Letters, 9.18, 3599-3601 (2007)
Amide bond formation via C (sp 3)?H bond functionalization and CO insertion
Liu, Huizhen, et al.
Chemical Communications (Cambridge, England), 50.3, 341-343 (2014)

Artículos

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P-Phos ligand family enhances catalysis, featuring atropisomeric biaryl bisphosphine with unique structural elements.

P-Phos ligand family enhances catalysis, featuring atropisomeric biaryl bisphosphine with unique structural elements.

P-Phos ligand family enhances catalysis, featuring atropisomeric biaryl bisphosphine with unique structural elements.

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