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678635

Sigma-Aldrich

1,2-双[(2R,5R)-2,5-二甲基磷]一氧化苯

kanata purity

别名:

(2R,5R)-1-{2-[(2R,5R)-2,5-二甲基磷-1-基]苯基}-2,5-二甲基磷烷 1-氧化物, R,R-Me-BozPhos

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About This Item

经验公式（希尔记法）:
C18H28OP2
CAS号:
638132-66-8
分子量:
322.36
MDL编号:
MFCD09750450
UNSPSC代码:
12352005
PubChem化学物质编号:
24885440
NACRES:
NA.22

表单

solid

旋光性

[α]22/D -171°, c = 1 in chloroform

mp

116-122 °C

官能团

phosphine oxide
phosphine

SMILES字符串

C[C@@H]1CC[C@@H](C)P1(C2=CC=CC=C2P3[C@H](C)CC[C@H]3C)=O

InChI

1S/C18H28OP2/c1-13-9-10-14(2)20(13)17-7-5-6-8-18(17)21(19)15(3)11-12-16(21)4/h5-8,13-16H,9-12H2,1-4H3/t13-,14-,15-,16-/m1/s1

InChI key

ORZVYNTUPREFTI-KLHDSHLOSA-N

一般描述

1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene monooxide is a chiral ligand whose copper complexes are used extensively in many organic reactions such as addition to imines, nitroalkenes, and reduction of β,β-disubstituted vinyl sulfones.

应用

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands
1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene monoxide can be used:
  • As a ligand in the preparation of dihydroquinolones and dihydroisoquinolones through palladium-catalyzed C-H functionalization of cyclopropane derivatives.
  • As an organocatalyst in the [4+1] annulation reactions of 2-enoylpyridine pyridine N-oxides and olefins with Morita-Baylis-Hillman (MBH) carbonates to yield dihydrofurans derivatives enantioselectively.
  • As a ligand in the copper-catalyzed synthesis of chiral nitroalkanes via the addition of dialkylzinc to β-nitroalkenes.

法律信息

与 Kanata Chemical Technologies Inc. 联合销售，仅供研究使用。这些化合物由 E.I. du Pont de Nemours and Company 授权制造和销售，此许可不包括利用这些化合物制备在制药领域销售的产品的权利。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

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分析证书(COA)

Lot/Batch Number
02205DH

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Utilization of BozPhos as an Effective Ligand in Enantioselective C-H Functionalization of Cyclopropanes: Synthesis of Dihydroisoquinolones and Dihydroquinolones
Mayer C, et al.
Organic Letters, 21(8), 2639-2644 (2019)
Enantioselective Construction of Pyridine N-Oxides Featuring 2, 3-Dihydrofuran Motifs via Phosphine-Catalyzed [4+ 1]-Annulation of 2-Enoylpyridine N-Oxides with Morita-Baylis-Hillman Carbonates
Zhang P, et al.
Organic Letters, 21(1), 152-155 (2018)
Application of the chiral bis (phosphine) monoxide ligand to catalytic enantioselective addition of dialkylzinc reagents to β-Nitroalkenes
Cote A, et al.
Organic Letters, 9(1), 85-87 (2007)
Organocatalytic enantioselective [1+ 4] annulation of Morita-Baylis-Hillman carbonates with electron-deficient olefins: Access to chiral 2, 3-dihydrofuran derivatives
Cheng Y, et al.
Organic Letters, 19(18), 4774-4777 (2017)
(R,R)?Me?DuPHOS Monoxide
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2011)

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