743585
(S)-(−)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline
≥95.0% (qNMR)
别名:
(S)-QUINAP
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关于此项目
经验公式（希尔记法）:
C31H22NP
化学文摘社编号:
分子量:
439.49
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Beilstein/REAXYS Number:
6664856
Assay:
≥95.0% (qNMR)
Form:
crystals
assay
≥95.0% (qNMR)
form
crystals
optical purity
enantiomeric excess: ≥98.0%
storage temp.
2-8°C
InChI
1S/C31H22NP/c1-3-13-25(14-4-1)33(26-15-5-2-6-16-26)29-20-19-23-11-7-9-17-27(23)30(29)31-28-18-10-8-12-24(28)21-22-32-31/h1-22H
InChI key
YMJAIEYASUCCMJ-UHFFFAOYSA-N
General description
(S)-QUINAP is a bidentate ligand used in catalytic asymmetric hydroboration, hydrogenation, oxidation, and allylic alkylation reactions.
Application
(S)-QUINAP can be used as a ligand:
[Ir(cod)Cl]2 treated with ligand (S)-QUINAP forms an iridium complex. This complex is used as a catalyst for the enantioselective hydrogenation of olefins. (S)-QUINAP–Rh complex can be employed as a catalyst in enantioselective hydroboration/oxidation of perfluoroalkenes.
- In the asymmetric hydrosilylation of alkyl and α, β-unsaturated ketones in the presence of Fe(OAc)2.
- For the synthesis of chiral organoboron compounds by copper-catalyzed β-borylation of α,β-unsaturated esters.
[Ir(cod)Cl]2 treated with ligand (S)-QUINAP forms an iridium complex. This complex is used as a catalyst for the enantioselective hydrogenation of olefins. (S)-QUINAP–Rh complex can be employed as a catalyst in enantioselective hydroboration/oxidation of perfluoroalkenes.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Practical Preparation and Resolution of 1-(2 `-Diphenylphosphino-1 `-naphthyl) isoquinoline: A Useful Ligand for Catalytic Asymmetric Synthesis
Lim CW, et al.
Organic Process Research & Development, 7(3), 379-384 (2003)
Anna M Segarra et al.
Chemical communications (Cambridge, England), (4), 464-465 (2004-02-07)
Enantioselective access to Markovnikov regioisomeric perfluoroalcohols is achieved in the presence of chiral cationic rhodium complexes and specific hydroborating reagents.
Enantioselective hydrogenation of olefins with axial chiral iridium QUINAP complex
Li X, et al.
Tetrahedron Letters, 48(22), 3915-3917 (2007)
全球贸易项目编号
| 货号 | GTIN |
|---|---|
| 743585-50MG | 04061833555637 |
| 743585-250MG | 04061833555620 |