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Merck
CN

696064

Sigma-Aldrich

(S)-C3-TunePhos

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别名:
(S)-二(二苯基膦基)-7,8-二氢-6H-二苯并[f,h][1,5]二噁壬英
经验公式(希尔记法):
C39H32O2P2
分子量:
594.62
MDL编号:
UNSPSC代码:
12352005
PubChem化学物质编号:

形式

powder

InChI

1S/C39H32O2P2/c1-5-16-30(17-6-1)42(31-18-7-2-8-19-31)36-26-13-24-34-38(36)39-35(41-29-15-28-40-34)25-14-27-37(39)43(32-20-9-3-10-21-32)33-22-11-4-12-23-33/h1-14,16-27H,15,28-29H2

InChI key

GTIXSUJKFAATAE-UHFFFAOYSA-N

应用

Chiral Quest Phosphine Ligands for Asymmetric Hydrogenation

Reactant for:
  • Asymmetric hydrogenation of ketones with TunePhos/diamine/ruthenium complexes
  • Stereoselective preparation of arylalkyl esters via enantioselective hydrogenation of enol acetates

Precatalyst for:
  • Enantioselective iridium-catalyzed carbonyl allylation from alcohol or aldehyde by transfer hydrogenative coupling of allyl acetate

Catalyst for:
  • Enantioselective hydrogenation of a-keto esters to a-hydroxy esters using Ru-tunephos catalysts
在钌催化的 β-酮酯、环 β-(酰胺基)丙烯酸酯和 α-邻苯二甲酰亚胺酮的不对称性氢化反应中可以提供与 BINAP 相当或更好的对映选择性以及催化能力。

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

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Wenjun Tang et al.
Journal of the American Chemical Society, 125(32), 9570-9571 (2003-08-09)
Hydrogenation of a series of cyclic beta-(acylamino)acrylates with tetrasubstituted olefins has been accomplished successfully with the use of Ru catalysts with chiral biaryl ligands such as C3-TunaPhos, and up to over 99% ee's have been achieved. This methodology provides an
Synthesis of chiral bisphosphines with tunable bite angles and their applications in asymmetric hydrogenation of beta-ketoesters.
Z Zhang et al.
The Journal of organic chemistry, 65(19), 6223-6226 (2000-09-16)
Aiwen Lei et al.
Journal of the American Chemical Society, 126(6), 1626-1627 (2004-02-12)
A new type of alpha-phthalimide ketones was hydrogenated in excellent enantioselectivity by using a Ru-(C3-TunePhos) complex as the catalyst. Up to 10 000 turnovers have been achieved in more than 99% ee in the hydrogenation reaction. A dynamic kinetic resolution

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