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
Beilstein:
6664856
MDL编号:
UNSPSC代码:
12352005
PubChem化学物质编号:
NACRES:
NA.22
方案
≥95.0% (qNMR)
表单
crystals
光学纯度
enantiomeric excess: ≥98.0%
储存温度
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
一般描述
(S)-QUINAP is a bidentate ligand used in catalytic asymmetric hydroboration, hydrogenation, oxidation, and allylic alkylation reactions.
应用
(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.
警示用语：
Warning
危险分类
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
靶器官
Respiratory system
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
Iron-catalyzed enantioselective hydrosilylation of ketones.
Nadim S Shaikh et al.
Angewandte Chemie (International ed. in English), 47(13), 2497-2501 (2008-02-26)
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)
William J Fleming et al.
Organic & biomolecular chemistry, 7(12), 2520-2524 (2009-06-09)
The synthesis and resolution of a new axially chiral Quinazolinap ligand are reported. The application of this and other related P-N ligands to the copper catalyzed beta-borylation of alpha,beta-unsaturated esters resulted in conversions of up to 100% and ee values
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