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Merck
모든 사진(1)

주요 문서

678635

Sigma-Aldrich

1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene monooxide

kanata purity

동의어(들):

(2R,5R)-1-{2-[(2R,5R)-2,5-Dimethylphospholan-1-yl]phenyl}-2,5-dimethylphospholane 1-oxide, R,R-Me-BozPhos

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About This Item

실험식(Hill 표기법):
C18H28OP2
CAS Number:
Molecular Weight:
322.36
MDL number:
UNSPSC 코드:
12352005
PubChem Substance ID:
NACRES:
NA.22

양식

solid

광학 활성

[α]22/D -171°, c = 1 in chloroform

mp

116-122 °C

작용기

phosphine oxide
phosphine

SMILES string

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

일반 설명

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.[1][2][3][4][5]

애플리케이션

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.[2]
  • As an organocatalyst in the [4+1] annulation reactions of 2-enoylpyridine pyridine N-oxides[3] and olefins[4] 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.[5]

법적 정보

Sold in collaboration with Kanata Chemical Technologies Inc. for research purposes only. These compounds were made and sold under license from E.I. du Pont de Nemours and Company, which license does not include the right to use the compounds in producing products for sale in the pharmaceutical field.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable


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문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

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)
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)
(R,R)?Me?DuPHOS Monoxide
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2011)
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)
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)

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